Boston, Massachusetts is a beautiful city that cannot be missed when doing a fall vacation on the East Coast of the United States! In fact, Boston makes for the perfect girl’s weekend getaway and I cannot wait to show you why.
The city of Boston is the capital of Massachusetts and it was named after a town in England. It’s one of the most popular and abundant cities in the USA and was also home to the Boston Tea Party in the late 1700s. Nowadays, the quaint U.S. city is in New England and is filled with charming neighborhoods, the best restaurants, fun bars, beautiful parks and many historic sites.
Overall, Boston (also known as Beantown) is the perfect place to visit in the fall, especially during a girl’s getaway weekend. I’ve visited Boston three times, once in November 2017 and the other two times during October 2020 and 2023. Boston makes for one of the best fall weekend trips from NJ.
What’s nice about visiting Boston during the fall is that it’s surrounded by charming small towns and picturesque rural areas that are easy to explore from the city. Adventuring to places like Salem, the White Mountains of New Hampshire, the Green Mountains of Vermont and the Berkshires will not disappoint you.
Boston is one of my favorite cities during autumn. In this article, discover the best things to do during a girl’s weekend in Boston, MA.
**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. While in Boston, The Liberty Hotel hosted me. I was also hosted for a meal at Lifted.
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Traveling for a Girl’s Weekend in Boston:
Since Boston is a larger city, you can easily travel there from anywhere worldwide by taking a flight to Boston Logan International Airport. You can find affordable flights through Skyscanner!
Other ways to get to Boston are through public transportation. The Amtrak train runs from major U.S. cities like New York, Philadelphia and Washington D.C. and takes passengers to Boston daily. If you’re coming from the New York City area, as I did, you can either drive to Boston or take a Flixbus.
From the New York City area, it’s around a three-and-a-half-hour drive to get to Boston, MA, depending on traffic. It takes about five hours to drive from Philadelphia to this stunning fall city, and from Washington, D.C., it’s over a seven-hour journey. If you decide to drive to Boston and don’t want to put miles on your vehicle or don’t have a car to take with you, it’s best to rent one.
If you fly into Boston and want to do a New England fall road trip from there, you’ll also need to rent a car to get around.
For those who fly into Boston, the best way to get from the airport to your accommodation is via a taxi or rideshare. Another way to get to your hotel is through Go Airport Shuttle!
Getting around the capital city is easy. Many of Downtown Boston’s main attractions are a short walk from each other, but if you need to use public transportation, it’s best to utilize the MBTA bus and railway lines. The “T” is Boston’s subway, running throughout the heart of the city and into Cambridge and the nearby suburbs.
Other ways to get around Boston are through a rideshare (Uber or Lyft), city taxis or the Hop On/Hop Off Trolley. Another great way to get around and see the city is by doing one of the Duck Tours, which is a bus and boat tour.
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Where to Stay in Boston for a Girl’s Weekend:
If you’re wondering where is the best place to stay in Boston during a ladies’ trip, I suggest The Liberty Hotel. This Luxury Collection Hotel by Marriott Bonvoy is in Beacon Hill and before it became a premier Boston accommodation, The Liberty Hotel was the Charles Street Jail. The jail was completed in 1851 and operated for over 120 years.
From 1851 through 1973, the jail housed some of Boston’s most notorious criminals. The prisoners later revolted because of poor living conditions and the jail ended up being declared unfit as it violated their constitutional rights.
On Memorial Day in 1990, the last prisoners were moved to the new Suffolk County Jail. In the early 2000s, the old jail was remodeled into a beautiful, luxurious, innovative hotel. Apart from renovating the building, the jail’s granite exterior and expansive interiors remained unchanged.
The jail cells were wrought-iron gates in the hotel lobby, restaurant and bar. They are examples of preservation!
Not only do the jail features and perfect location make this hotel one of the best places to stay in Boston during a girl’s weekend, but the entire place draws young people from all over the city looking to have a good time.
Staying at The Liberty Hotel in Boston:
There are 298 rooms and suites at The Liberty Hotel. Each room and suite have been renovated to maintain the historic nature of the original building.
While at The Liberty Hotel, I stayed in one of the Deluxe Rooms. Featuring either a king or two queen beds, the Deluxe Rooms at The Liberty Hotel feature floor-to-ceiling windows and include a 55-inch flat panel HD-LCD television, en-suite bathroom with Molton Brown bath products, a mini-bar, comfy bathrobes and more.
The other guest rooms you can book for your girl’s trip to Boston are Superior King or Queen Rooms, Deluxe Courtyard King Rooms, Grand Deluxe City View Rooms and Grand Deluxe Corner Rooms.
Regarding suites, you can book the Charles River Suite, a one-bedroom suite with a master bedroom, one and a half bathrooms, a separate living room and dining area and beautiful views of the Boston skyline and Charles River. You can also book the Ebersol Suite, which has panoramic views of Boston from the State House in the east to Charlestown in the north.
Food and Entertainment at The Liberty Hotel:
One of the best things to do in Boston during a girl’s weekend is to enjoy late-night fun and morning brunch at The Liberty Hotel’s restaurants and bars.
Liberty Bar: Located in the center of the hotel, the Liberty Bar is a great place to casually grab food and after-work drinks. I say that because happy hour is illegal in Boston, Massachusetts. The spicy margarita and pizza are my favorite things to order at the Liberty Bar.
All food and drinks ordered from the Liberty Bar’s menu can be enjoyed on the hotel’s Catwalk on a first-come-first-serve basis.
Alibi: If you want to enjoy a girl’s night, you must visit Alibi, located on the bottom level of The Liberty. Set in the old “drunk tank” of the jail, Alibi features original brick cell walls.
At Alibi, you can enjoy late-night cocktails, tasty bites and dancing! What is cool about Alibi is that celebrity mug shots are scattered along the bar’s walls.
You can see the mug shots of Jay-Z, Lindsay Lohan, Justin Bieber and Matthew McConaughey. These celebrities weren’t inmates in this specific jail, but seeing their mug shots from when they were arrested was interesting.
Even though this trendy lounge has DJs and entertainment from Thursday through Saturday nights, Friday nights are usually when it’s most crowded!
CLINK.: The best place to brunch in Boston is The Liberty’s CLINK. restaurant. Executive Chef Daniel Kenney offers a creative menu for guests to enjoy fresh North Atlantic seafood, seasonal New England fare, heirloom produce and more.
The restaurant features restored jail details and architecture but boasts big windows that let natural light in while you savor your meal.
If you’re a fan of Bloody Mary’s, you must enjoy the DIY bar to make your own drink! There are also other great cocktails you can sip at CLINK.
In addition to the above, The Liberty Hotel also has another fine-dining Italian restaurant called Scampo, featuring Mediterranean dishes by Boston-based Chef Lydia Shire.
I also loved staying at The Liberty Hotel because there is complimentary coffee and tea in the morning near the museum, where you can learn more about the former Charles Street Jail. In addition, you can also take your morning beverage out to The Yard and enjoy the beautiful fall foliage. (Sometimes yoga classes are held in The Yard during the warmer months.)
Where to Eat and Drink During a 3-day Boston Itinerary:
It’s no secret that Boston has some of the most incredible restaurants in the United States!
From historic seafood restaurants in the North End to family-run eateries in Boston’s Little Italy and brunch spots in the South End to quaint coffee shops in Beacon Hill, below is where you must eat in Beantown during a girl’s weekend:
Tatte Bakery: One of the best places to grab breakfast in Boston is Tatte Bakery. With locations all over the city, Tatte Bakery was founded by Tzurit Or, who was born in Israel and is a former film producer.
At Tatte Bakery, you can enjoy a variety of specialty coffees and lattes, pastries, breakfast sandwiches and more. I visited the Seaport location in October 2023 and enjoyed the smoked salmon, avocado and egg sandwich and it was delicious!
Union Oyster House: Recognized as Boston’s oldest restaurant, Union Oyster House is a National Historic Landmark Reserve on the Freedom Trail.
It’s best to visit this seafood restaurant on a Sunday, where you can watch a game and enjoy mimosas, tasty oysters and heartwarming New England clam chowder. I’m happy I finally visited this spot during my Boston to Maine fall road trip!
Lifted: Located at the Omni Boston Hotel at the Seaport, Lifted is a rooftop urban oasis that serves delicious contemporary food and cocktails.
During my most recent girl’s getaway to Boston in October 2023, I enjoyed a sangria with a salted caramel lobster roll and charred Brussels sprouts during an evening at this fun spot.
State Street Provisions: An excellent modern tavern with rustic charm, State Street Provisions is a local favorite in the Long Wharf area. I visited this location during a girl’s trip in October 2020.
While at State Street Provisions, I enjoyed a tasty Angry Queen Pizza, equivalent to a Margherita pizza, with a fall sangria. Nothing disappointed! It’s the perfect place to visit during a Boston girl’s weekend.
Pauli’s: Featured on the Food Network’s Diners, Drive-Ins and Dives, Pauli’s is a great, four-generations, family-owned deli where you can enjoy classic New England lobster rolls, overstuffed sandwiches, fresh salads and more.
Situated on the North End, I visited Pauli’s during my first time in Boston and had the Zagat-rated, hot and buttery Connecticut lobster roll, which was delicious!
Dolce Vita Ristorante: Located in Boston’s renowned Little Italy neighborhood, Dolce Vita Ristorante is one of the best restaurants to enjoy dinner if you’re craving Italian cuisine.
Born in the Sicilian small town of Aragona, owner Franco Graceffa grew up knowing the best Italian cooking. He opened Dolce Vita Ristorante in 1990 and serves delicious dishes that will leave you full and happy!
During my November 2017 trip, I visited Dolce Vita Ristorante and savored fettuccine with jumbo shrimp and scallops in a white wine tomato sauce with fresh sun-dried tomatoes.
Mike’s Pastry and Modern Pastry Shop: Located in Boston’s North End, along with Cambridge, Somerville and TD Garden, Mike’s Pastry was founded in 1946 and is known as one of the best Italian pastry shops in the city.
Owner Michael Mercogliano created a one-of-a-kind cannoli that keeps locals and tourists returning for more. It’s a fantastic pastry shop to get cannoli, pastries, Italian cookies, pies, cakes and gelato. I visited Mike’s Pastry when I traveled to Boston in October 2020.
During my recent trip to Boston in October 2023, I visited Modern Pastry Shop, which was also incredible. This award-winning Italian pastry shop was founded by the Picariello family in 1930.
At Modern Pastry Shop, you can build your own cannoli and choose from various Italian cookies. This popular pastry shop also has cakes, Italian specialty snacks, chocolates, fudge and more.
Faneuil Hall Marketplace: If you’re a foodie, you must visit Faneuil Hall Marketplace, home to the world-famous Quincy Market. It’s the largest and oldest food hall in the country.
At Quincy Market, you can savor great food from fresh seafood, ice cream, Mexican cuisine, Asian fare, Korean hot dogs, pizza, sushi, bubble tea and more.
The Best Itinerary for a Girl’s Weekend in Boston:
Wander through Beacon Hill:
A girl’s weekend in Boston would not be complete without getting lost in the cobbled streets of Beacon Hill, the city’s most charming area. It’s also one of Boston’s oldest neighborhoods!
Featuring beautiful Federal-style houses, Beacon Hill is recognized for its narrow, gas-lit streets and brick sidewalks. It’s regarded as one of Boston, Massachusetts’ most desirable and expensive areas.
Discover 5 misconceptions and 5 truths about life in Boston!
Some of the best things to do in Beacon Hill in Boston are to stroll through the cobblestone streets, stop at the most beautiful flower shop – Rouvalis Flowers, make your way into a coffee shop, visit Beacon Hill Books & Café, walk through an antique store and grab brunch with your best girlfriends!
Walk through the Boston Public Garden and Boston Common:
Two great places to walk around in the city during fall trips in Boston are the Boston Common and Boston Public Garden. Both parks are connected and are beautiful spots to see vibrant fall colors.
The Boston Common is a 50-acre urban park that hosted British troops during the American Revolution. Over the past several decades, the Boston Common has been a stage for free speech.
Part of the National Park Service, the Boston Public Garden was the first public botanical garden in the United States. In this park, you can find beautiful Victorian gardens, statues, stunning fountains, various trees and plants and more.
Learn about Boston’s History on the Freedom Trail:
Boston is one of the most historic cities in the United States. One of the best ways to learn about the city’s history is to conquer the Freedom Trail.
The Freedom Trail is a 2.5-mile trail that passes by 17 significant historical locations. It’s also part of the National Park Service. You can do a self-guided tour of the Freedom Trail by downloading the Freedom Trail Tour App, so sign up for a guided tour.
Doing a guided tour is a fun way to taste Boston’s history. You can sign up here for these tours! The historical sites you’ll see on the Freedom Trail are Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel Burying Ground, Benjamin Franklin Statue, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution and Bunker Hill Monument.
Make a Visit to the Cheers Bar:
Located across the street from the Public Garden is the iconic Cheers Bar from the Nick At Nite sitcom Cheers!
I used to watch Cheers at night in elementary school, so of course, the bar was high on my bucket list to visit during my first girl’s weekend getaway to Boston in the fall of 2017. It’s a great place to grab a beer and some light snacks!
The Cheers Bar is bigger than you’d imagine! It’s a fun and interactive experience to add to your Boston weekend trip itinerary. There are three other rooms at the Cheers Bar: the original bar where they shot the sitcom, a restaurant area and another bar that overlooks the park. There are several gift shops and it’s also attached to an exclusive venue called Hampshire House.
Shop Your Way through Newbury Street:
Like NYC has 5th Avenue and LA has Rodeo Drive, Boston has Newbury Street. This swanky street in Back Bay runs east to west from the Boston Public Garden to Brookline Avenue.
On Newbury Street, you can find high-end fashion design stores like Tiffany & Co. and Cartier, women’s retail shops like Zara and Lululemon, wine bars, restaurants, coffee shops and locally owned boutiques.
Stroll around the Seaport District:
The Seaport District is one of Boston’s most beautiful and peaceful areas to enjoy on a girl’s trip. It features stunning views of the Boston Harbor, great brunch and coffee joints, luxury hotels, seafood restaurants, breweries and more.
The best thing to do in Boston’s Seaport District is to stroll part of the Boston Harborwalk, a 43-mile walkway along the city’s shoreline. Fan Pier Park is one of the most picturesque spots in the capital!
Other fun things to do during a girl’s weekend trip to Boston are to visit the Institute of Contemporary Art and Boston Tea Party Ships & Museum. You must also make memories at Puttshack, an indoor mini golf course, visit Harpoon Brewery’s Oktoberfest and do a Boston Harbor cruise.
Attend a Sporting Event during Your Boston Weekend Trip:
What’s great about traveling to Boston during fall is that not only is it football season, but it’s still baseball season! It’s a must to see the New England Patriots play at Gillette Stadium or the Boston Red Sox at Fenway Park.
During a girl’s weekend in Boston, Fenway Park is a fun area to grab a drink, listen to live music and visit Boston’s Museum of Fine Arts and the Isabella Stewart Gardner Museum. Not only do the Red Sox play at Fenway Park, but concerts are also held there year-round!
Enjoy an Afternoon at a Boston Brewery:
A girl’s trip to Boston is incomplete without visiting a brewery. There are a lot of great ones around the city!
Samuel Adams Brewery: Known as Boston’s most famous lager, Samuel Adams is a must-visit when you’re in the city during a girl’s weekend. Please note that the brewery is closed on Sundays.
Each year, beer enthusiasts at Sam Adams travel to Germany to select the world’s best heirloom aroma hops for their lager.
Harpoon Brewery: Located in South Boston on the Boston Main Channel, Harpoon Brewery is a lively spot to appreciate seasonal beers, live music, food trucks and more.
Harpoon Brewery is a lively and fun bier hall with renowned beers straight from the source as well as German and American food. I love the UFO flights!
Cambridge Brewing Co.: One of my favorite breweries in Boston is Cambridge Brewing Co. A trip to Boston is incomplete without exploring Cambridge, including Harvard University.
Located in Kendall Square, Cambridge Brewing Co. is the oldest brewpub in the Greater Boston area and it offers flavor-forward beers using only water, malt, hops and yeast. They also have delicious sandwiches, salads, healthy bowls, burgers and more.
Have a Girl’s Night Out in Boston:
You must enjoy a night out around the Seaport during a girl’s trip to Boston. Below are two great places to grab a drink with friends:
Drink: This fun speakeasy blends classic cocktails of the prohibition era with modern artisanal ingredients.
After you find a seat at Drink, a bartender will approach you and ask what flavors you like in a cocktail. I visited this spot in 2017 and had a maple syrup-related craft cocktail.
Sporting Club: If you’re looking for a fun place to go on a Sunday night to watch a football game, you must go to the Sporting Club at the Omni Boston at the Seaport.
This fantastic spot features 12 high-definition televisions for everyone to watch the game. You can also enjoy globally inspired crafted food, specialty cocktails, a variety of beers on tap and more!
Do a Day Trip to Salem during a Boston Girl’s Trip:
If you’re looking for a fun and festive place to visit from Boston that will get you into the Halloween spirit, you must go to Salem for the day! This city is famous for the Salem Witch Trials and being the filming location for Disney’s Hocus Pocus.
During a day trip to Salem, you must learn about the 1692 Salem Witch Trials by visiting the Salem Witch Museum, The Witch House, House of the Seven Gables and participating in a Salem walking tour. Salem also has interesting haunts, so doing a ghost tour is a must.
You must also visit the Hocus Pocus filming locations, enter one of the shops on Essex Street, visit Salem’s best restaurants and bars like Ledger and Notch Brewery and more.
Other trips you must take with your girlfriends:
7-Day New England Fall Road Trip Itinerary
A Perfect Girl’s Getaway at Woolverton Inn
Best Girl Trip Destinations in the World
I hope you all enjoyed reading about the best things to do during a girl’s weekend in Boston, Massachusetts. If you have any questions about my time in Boston, please email me at info@browneyedflowerchild.com.
Basic Facts of the United States:
Currency: United States Dollar, Capital: Washington D.C., MA State Capital: Boston, Time Zone: Eastern Standard Time
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Boston, Massachusetts is a beautiful city that cannot be missed when doing a fall vacation on the East Coast of the United States! In fact, Boston makes for the perfect girl’s weekend getaway and I cannot wait to show you why.
The city of Boston is the capital of Massachusetts and it was named after a town in England. It’s one of the most popular and abundant cities in the USA and was also home to the Boston Tea Party in the late 1700s. Nowadays, the quaint U.S. city is in New England and is filled with charming neighborhoods, the best restaurants, fun bars, beautiful parks and many historic sites.
Overall, Boston (also known as Beantown) is the perfect place to visit in the fall, especially during a girl’s getaway weekend. I’ve visited Boston three times, once in November 2017 and the other two times during October 2020 and 2023. Boston makes for one of the best fall weekend trips from NJ.
What’s nice about visiting Boston during the fall is that it’s surrounded by charming small towns and picturesque rural areas that are easy to explore from the city. Adventuring to places like Salem, the White Mountains of New Hampshire, the Green Mountains of Vermont and the Berkshires will not disappoint you.
Boston is one of my favorite cities during autumn. In this article, discover the best things to do during a girl’s weekend in Boston, MA.
**Please note that this blog post uses affiliate links meaning that if you make a purchase via my affiliate link, I receive a small commission at no additional cost to you. I only promote and talk about products and services that I have used and like. While in Boston, The Liberty Hotel hosted me. I was also hosted for a meal at Lifted.
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Traveling for a Girl’s Weekend in Boston:
Since Boston is a larger city, you can easily travel there from anywhere worldwide by taking a flight to Boston Logan International Airport. You can find affordable flights through Skyscanner!
Other ways to get to Boston are through public transportation. The Amtrak train runs from major U.S. cities like New York, Philadelphia and Washington D.C. and takes passengers to Boston daily. If you’re coming from the New York City area, as I did, you can either drive to Boston or take a Flixbus.
From the New York City area, it’s around a three-and-a-half-hour drive to get to Boston, MA, depending on traffic. It takes about five hours to drive from Philadelphia to this stunning fall city, and from Washington, D.C., it’s over a seven-hour journey. If you decide to drive to Boston and don’t want to put miles on your vehicle or don’t have a car to take with you, it’s best to rent one.
If you fly into Boston and want to do a New England fall road trip from there, you’ll also need to rent a car to get around.
For those who fly into Boston, the best way to get from the airport to your accommodation is via a taxi or rideshare. Another way to get to your hotel is through Go Airport Shuttle!
Getting around the capital city is easy. Many of Downtown Boston’s main attractions are a short walk from each other, but if you need to use public transportation, it’s best to utilize the MBTA bus and railway lines. The “T” is Boston’s subway, running throughout the heart of the city and into Cambridge and the nearby suburbs.
Other ways to get around Boston are through a rideshare (Uber or Lyft), city taxis or the Hop On/Hop Off Trolley. Another great way to get around and see the city is by doing one of the Duck Tours, which is a bus and boat tour.
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Where to Stay in Boston for a Girl’s Weekend:
If you’re wondering where is the best place to stay in Boston during a ladies’ trip, I suggest The Liberty Hotel. This Luxury Collection Hotel by Marriott Bonvoy is in Beacon Hill and before it became a premier Boston accommodation, The Liberty Hotel was the Charles Street Jail. The jail was completed in 1851 and operated for over 120 years.
From 1851 through 1973, the jail housed some of Boston’s most notorious criminals. The prisoners later revolted because of poor living conditions and the jail ended up being declared unfit as it violated their constitutional rights.
On Memorial Day in 1990, the last prisoners were moved to the new Suffolk County Jail. In the early 2000s, the old jail was remodeled into a beautiful, luxurious, innovative hotel. Apart from renovating the building, the jail’s granite exterior and expansive interiors remained unchanged.
The jail cells were wrought-iron gates in the hotel lobby, restaurant and bar. They are examples of preservation!
Not only do the jail features and perfect location make this hotel one of the best places to stay in Boston during a girl’s weekend, but the entire place draws young people from all over the city looking to have a good time.
Staying at The Liberty Hotel in Boston:
There are 298 rooms and suites at The Liberty Hotel. Each room and suite have been renovated to maintain the historic nature of the original building.
While at The Liberty Hotel, I stayed in one of the Deluxe Rooms. Featuring either a king or two queen beds, the Deluxe Rooms at The Liberty Hotel feature floor-to-ceiling windows and include a 55-inch flat panel HD-LCD television, en-suite bathroom with Molton Brown bath products, a mini-bar, comfy bathrobes and more.
The other guest rooms you can book for your girl’s trip to Boston are Superior King or Queen Rooms, Deluxe Courtyard King Rooms, Grand Deluxe City View Rooms and Grand Deluxe Corner Rooms.
Regarding suites, you can book the Charles River Suite, a one-bedroom suite with a master bedroom, one and a half bathrooms, a separate living room and dining area and beautiful views of the Boston skyline and Charles River. You can also book the Ebersol Suite, which has panoramic views of Boston from the State House in the east to Charlestown in the north.
Food and Entertainment at The Liberty Hotel:
One of the best things to do in Boston during a girl’s weekend is to enjoy late-night fun and morning brunch at The Liberty Hotel’s restaurants and bars.
Liberty Bar: Located in the center of the hotel, the Liberty Bar is a great place to casually grab food and after-work drinks. I say that because happy hour is illegal in Boston, Massachusetts. The spicy margarita and pizza are my favorite things to order at the Liberty Bar.
All food and drinks ordered from the Liberty Bar’s menu can be enjoyed on the hotel’s Catwalk on a first-come-first-serve basis.
Alibi: If you want to enjoy a girl’s night, you must visit Alibi, located on the bottom level of The Liberty. Set in the old “drunk tank” of the jail, Alibi features original brick cell walls.
At Alibi, you can enjoy late-night cocktails, tasty bites and dancing! What is cool about Alibi is that celebrity mug shots are scattered along the bar’s walls.
You can see the mug shots of Jay-Z, Lindsay Lohan, Justin Bieber and Matthew McConaughey. These celebrities weren’t inmates in this specific jail, but seeing their mug shots from when they were arrested was interesting.
Even though this trendy lounge has DJs and entertainment from Thursday through Saturday nights, Friday nights are usually when it’s most crowded!
CLINK.: The best place to brunch in Boston is The Liberty’s CLINK. restaurant. Executive Chef Daniel Kenney offers a creative menu for guests to enjoy fresh North Atlantic seafood, seasonal New England fare, heirloom produce and more.
The restaurant features restored jail details and architecture but boasts big windows that let natural light in while you savor your meal.
If you’re a fan of Bloody Mary’s, you must enjoy the DIY bar to make your own drink! There are also other great cocktails you can sip at CLINK.
In addition to the above, The Liberty Hotel also has another fine-dining Italian restaurant called Scampo, featuring Mediterranean dishes by Boston-based Chef Lydia Shire.
I also loved staying at The Liberty Hotel because there is complimentary coffee and tea in the morning near the museum, where you can learn more about the former Charles Street Jail. In addition, you can also take your morning beverage out to The Yard and enjoy the beautiful fall foliage. (Sometimes yoga classes are held in The Yard during the warmer months.)
Where to Eat and Drink During a 3-day Boston Itinerary:
It’s no secret that Boston has some of the most incredible restaurants in the United States!
From historic seafood restaurants in the North End to family-run eateries in Boston’s Little Italy and brunch spots in the South End to quaint coffee shops in Beacon Hill, below is where you must eat in Beantown during a girl’s weekend:
Tatte Bakery: One of the best places to grab breakfast in Boston is Tatte Bakery. With locations all over the city, Tatte Bakery was founded by Tzurit Or, who was born in Israel and is a former film producer.
At Tatte Bakery, you can enjoy a variety of specialty coffees and lattes, pastries, breakfast sandwiches and more. I visited the Seaport location in October 2023 and enjoyed the smoked salmon, avocado and egg sandwich and it was delicious!
Union Oyster House: Recognized as Boston’s oldest restaurant, Union Oyster House is a National Historic Landmark Reserve on the Freedom Trail.
It’s best to visit this seafood restaurant on a Sunday, where you can watch a game and enjoy mimosas, tasty oysters and heartwarming New England clam chowder. I’m happy I finally visited this spot during my Boston to Maine fall road trip!
Lifted: Located at the Omni Boston Hotel at the Seaport, Lifted is a rooftop urban oasis that serves delicious contemporary food and cocktails.
During my most recent girl’s getaway to Boston in October 2023, I enjoyed a sangria with a salted caramel lobster roll and charred Brussels sprouts during an evening at this fun spot.
State Street Provisions: An excellent modern tavern with rustic charm, State Street Provisions is a local favorite in the Long Wharf area. I visited this location during a girl’s trip in October 2020.
While at State Street Provisions, I enjoyed a tasty Angry Queen Pizza, equivalent to a Margherita pizza, with a fall sangria. Nothing disappointed! It’s the perfect place to visit during a Boston girl’s weekend.
Pauli’s: Featured on the Food Network’s Diners, Drive-Ins and Dives, Pauli’s is a great, four-generations, family-owned deli where you can enjoy classic New England lobster rolls, overstuffed sandwiches, fresh salads and more.
Situated on the North End, I visited Pauli’s during my first time in Boston and had the Zagat-rated, hot and buttery Connecticut lobster roll, which was delicious!
Dolce Vita Ristorante: Located in Boston’s renowned Little Italy neighborhood, Dolce Vita Ristorante is one of the best restaurants to enjoy dinner if you’re craving Italian cuisine.
Born in the Sicilian small town of Aragona, owner Franco Graceffa grew up knowing the best Italian cooking. He opened Dolce Vita Ristorante in 1990 and serves delicious dishes that will leave you full and happy!
During my November 2017 trip, I visited Dolce Vita Ristorante and savored fettuccine with jumbo shrimp and scallops in a white wine tomato sauce with fresh sun-dried tomatoes.
Mike’s Pastry and Modern Pastry Shop: Located in Boston’s North End, along with Cambridge, Somerville and TD Garden, Mike’s Pastry was founded in 1946 and is known as one of the best Italian pastry shops in the city.
Owner Michael Mercogliano created a one-of-a-kind cannoli that keeps locals and tourists returning for more. It’s a fantastic pastry shop to get cannoli, pastries, Italian cookies, pies, cakes and gelato. I visited Mike’s Pastry when I traveled to Boston in October 2020.
During my recent trip to Boston in October 2023, I visited Modern Pastry Shop, which was also incredible. This award-winning Italian pastry shop was founded by the Picariello family in 1930.
At Modern Pastry Shop, you can build your own cannoli and choose from various Italian cookies. This popular pastry shop also has cakes, Italian specialty snacks, chocolates, fudge and more.
Faneuil Hall Marketplace: If you’re a foodie, you must visit Faneuil Hall Marketplace, home to the world-famous Quincy Market. It’s the largest and oldest food hall in the country.
At Quincy Market, you can savor great food from fresh seafood, ice cream, Mexican cuisine, Asian fare, Korean hot dogs, pizza, sushi, bubble tea and more.
The Best Itinerary for a Girl’s Weekend in Boston:
Wander through Beacon Hill:
A girl’s weekend in Boston would not be complete without getting lost in the cobbled streets of Beacon Hill, the city’s most charming area. It’s also one of Boston’s oldest neighborhoods!
Featuring beautiful Federal-style houses, Beacon Hill is recognized for its narrow, gas-lit streets and brick sidewalks. It’s regarded as one of Boston, Massachusetts’ most desirable and expensive areas.
Discover 5 misconceptions and 5 truths about life in Boston!
Some of the best things to do in Beacon Hill in Boston are to stroll through the cobblestone streets, stop at the most beautiful flower shop – Rouvalis Flowers, make your way into a coffee shop, visit Beacon Hill Books & Café, walk through an antique store and grab brunch with your best girlfriends!
Walk through the Boston Public Garden and Boston Common:
Two great places to walk around in the city during fall trips in Boston are the Boston Common and Boston Public Garden. Both parks are connected and are beautiful spots to see vibrant fall colors.
The Boston Common is a 50-acre urban park that hosted British troops during the American Revolution. Over the past several decades, the Boston Common has been a stage for free speech.
Part of the National Park Service, the Boston Public Garden was the first public botanical garden in the United States. In this park, you can find beautiful Victorian gardens, statues, stunning fountains, various trees and plants and more.
Learn about Boston’s History on the Freedom Trail:
Boston is one of the most historic cities in the United States. One of the best ways to learn about the city’s history is to conquer the Freedom Trail.
The Freedom Trail is a 2.5-mile trail that passes by 17 significant historical locations. It’s also part of the National Park Service. You can do a self-guided tour of the Freedom Trail by downloading the Freedom Trail Tour App, so sign up for a guided tour.
Doing a guided tour is a fun way to taste Boston’s history. You can sign up here for these tours! The historical sites you’ll see on the Freedom Trail are Boston Common, Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel Burying Ground, Benjamin Franklin Statue, Old Corner Bookstore, Old South Meeting House, Old State House, Boston Massacre Site, Faneuil Hall, Paul Revere House, Old North Church, Copp’s Hill Burying Ground, USS Constitution and Bunker Hill Monument.
Make a Visit to the Cheers Bar:
Located across the street from the Public Garden is the iconic Cheers Bar from the Nick At Nite sitcom Cheers!
I used to watch Cheers at night in elementary school, so of course, the bar was high on my bucket list to visit during my first girl’s weekend getaway to Boston in the fall of 2017. It’s a great place to grab a beer and some light snacks!
The Cheers Bar is bigger than you’d imagine! It’s a fun and interactive experience to add to your Boston weekend trip itinerary. There are three other rooms at the Cheers Bar: the original bar where they shot the sitcom, a restaurant area and another bar that overlooks the park. There are several gift shops and it’s also attached to an exclusive venue called Hampshire House.
Shop Your Way through Newbury Street:
Like NYC has 5th Avenue and LA has Rodeo Drive, Boston has Newbury Street. This swanky street in Back Bay runs east to west from the Boston Public Garden to Brookline Avenue.
On Newbury Street, you can find high-end fashion design stores like Tiffany & Co. and Cartier, women’s retail shops like Zara and Lululemon, wine bars, restaurants, coffee shops and locally owned boutiques.
Stroll around the Seaport District:
The Seaport District is one of Boston’s most beautiful and peaceful areas to enjoy on a girl’s trip. It features stunning views of the Boston Harbor, great brunch and coffee joints, luxury hotels, seafood restaurants, breweries and more.
The best thing to do in Boston’s Seaport District is to stroll part of the Boston Harborwalk, a 43-mile walkway along the city’s shoreline. Fan Pier Park is one of the most picturesque spots in the capital!
Other fun things to do during a girl’s weekend trip to Boston are to visit the Institute of Contemporary Art and Boston Tea Party Ships & Museum. You must also make memories at Puttshack, an indoor mini golf course, visit Harpoon Brewery’s Oktoberfest and do a Boston Harbor cruise.
Attend a Sporting Event during Your Boston Weekend Trip:
What’s great about traveling to Boston during fall is that not only is it football season, but it’s still baseball season! It’s a must to see the New England Patriots play at Gillette Stadium or the Boston Red Sox at Fenway Park.
During a girl’s weekend in Boston, Fenway Park is a fun area to grab a drink, listen to live music and visit Boston’s Museum of Fine Arts and the Isabella Stewart Gardner Museum. Not only do the Red Sox play at Fenway Park, but concerts are also held there year-round!
Enjoy an Afternoon at a Boston Brewery:
A girl’s trip to Boston is incomplete without visiting a brewery. There are a lot of great ones around the city!
Samuel Adams Brewery: Known as Boston’s most famous lager, Samuel Adams is a must-visit when you’re in the city during a girl’s weekend. Please note that the brewery is closed on Sundays.
Each year, beer enthusiasts at Sam Adams travel to Germany to select the world’s best heirloom aroma hops for their lager.
Harpoon Brewery: Located in South Boston on the Boston Main Channel, Harpoon Brewery is a lively spot to appreciate seasonal beers, live music, food trucks and more.
Harpoon Brewery is a lively and fun bier hall with renowned beers straight from the source as well as German and American food. I love the UFO flights!
Cambridge Brewing Co.: One of my favorite breweries in Boston is Cambridge Brewing Co. A trip to Boston is incomplete without exploring Cambridge, including Harvard University.
Located in Kendall Square, Cambridge Brewing Co. is the oldest brewpub in the Greater Boston area and it offers flavor-forward beers using only water, malt, hops and yeast. They also have delicious sandwiches, salads, healthy bowls, burgers and more.
Have a Girl’s Night Out in Boston:
You must enjoy a night out around the Seaport during a girl’s trip to Boston. Below are two great places to grab a drink with friends:
Drink: This fun speakeasy blends classic cocktails of the prohibition era with modern artisanal ingredients.
After you find a seat at Drink, a bartender will approach you and ask what flavors you like in a cocktail. I visited this spot in 2017 and had a maple syrup-related craft cocktail.
Sporting Club: If you’re looking for a fun place to go on a Sunday night to watch a football game, you must go to the Sporting Club at the Omni Boston at the Seaport.
This fantastic spot features 12 high-definition televisions for everyone to watch the game. You can also enjoy globally inspired crafted food, specialty cocktails, a variety of beers on tap and more!
Do a Day Trip to Salem during a Boston Girl’s Trip:
If you’re looking for a fun and festive place to visit from Boston that will get you into the Halloween spirit, you must go to Salem for the day! This city is famous for the Salem Witch Trials and being the filming location for Disney’s Hocus Pocus.
During a day trip to Salem, you must learn about the 1692 Salem Witch Trials by visiting the Salem Witch Museum, The Witch House, House of the Seven Gables and participating in a Salem walking tour. Salem also has interesting haunts, so doing a ghost tour is a must.
You must also visit the Hocus Pocus filming locations, enter one of the shops on Essex Street, visit Salem’s best restaurants and bars like Ledger and Notch Brewery and more.
Other trips you must take with your girlfriends:
7-Day New England Fall Road Trip Itinerary
A Perfect Girl’s Getaway at Woolverton Inn
Best Girl Trip Destinations in the World
I hope you all enjoyed reading about the best things to do during a girl’s weekend in Boston, Massachusetts. If you have any questions about my time in Boston, please email me at info@browneyedflowerchild.com.
Basic Facts of the United States:
Currency: United States Dollar, Capital: Washington D.C., MA State Capital: Boston, Time Zone: Eastern Standard Time
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32 Comments
My husband and I have really been wanting to head to Boston for the longest time! Hopefully we can get there soon!
My favorite part of Boston is for sure Boston Common! Such a beautiful park! Great read Taylor!
I’ve been wanting to go to Boston for the longest time! I’d love to see the leaves during fall some time ? it looks like you had a great time there! And the photo of Boston from above is crazy beautiful!!
Such a nice trio, loved to read your experiences! Boston sounds like a perfect city for a weekend getaway! It’s our dream to visit the US one day, we can include Boston in our itinerary ?
I don’t know why but I have the feeling I would totally love Boston! Looking at your photos makes me wanna book a flight there immediately ☺️
Aww another beautiful blog post, Tay! Ya know I just went through Portland, Maine the other day and thought of you. Shame we didn’t make it to Boston!
I love Boston! It would be such a fun place for a girls weekend! The Samuel Adams Brewery was so fun. I also love wandering around the Boston Common and Public Gardens.
I love it in Boston! My uncle moved there a few years ago so we have been to visit a few times! Such a beautiful and calm city
oh my goodness that is SO cool you could see the Cheers bar! What a cool stop!
Boston has so many great breweries, and the Public Gardens are my favorite!
These are some great places to visit in Boston for a weekend away! Adding some of these stops to my list for when I visit the city.
I’ve been to Boston a couple of times but haven’t seen a lot of the places you posted! I will be saving this for my next trip out there!
Boston is such a great city. I really want to go back again soon. Last time I was there was with my friend and it was an amazing girls trip. We did some of the touristy stuff but also just enjoyed checking out the city. I need to visit some of those breweries though. Next time for sure
What a fun blog! I do love Boston. Learned so much. I would love to stay at the old jail cell Hotel. Very cool concept. I also love history so would enjoy the Paul Revere House and Boston Harbor. Great foo recommendations too!
I love Boston! Such a fun city with so much history and is a great weekend getaway ant time of the year. The Liberty Hotel is such a great place to stay for its unique history and fun decor!
I LOVED this post! I’m dying to explore Boston and your article listed so many incredible places! Such a fun read.
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My husband and I have really been wanting to head to Boston for the longest time! Hopefully we can get there soon!
It’s a great city and I highly recommend it for the fall! 🙂
My favorite part of Boston is for sure Boston Common! Such a beautiful park! Great read Taylor!
Yes, I loved the Spanish moss they had. It was so lovely!
I’ve been wanting to go to Boston for the longest time! I’d love to see the leaves during fall some time ? it looks like you had a great time there! And the photo of Boston from above is crazy beautiful!!
You definitely have to make your way to the Northeast of the United States during the fall season. It is so beautiful and you would love it! 🙂
Such a nice trio, loved to read your experiences! Boston sounds like a perfect city for a weekend getaway! It’s our dream to visit the US one day, we can include Boston in our itinerary ?
Thank you so much Zsuzsanna! I highly recommend to visit Boston during the fall season. It is so beautiful! 🙂
I don’t know why but I have the feeling I would totally love Boston! Looking at your photos makes me wanna book a flight there immediately ☺️
Yes, I loved it so much when I went almost two years ago. My cousin and I had such a blast and I totally recommend going in the fall! 🙂
Aww another beautiful blog post, Tay! Ya know I just went through Portland, Maine the other day and thought of you. Shame we didn’t make it to Boston!
Thank you so much Bri! Ah I hope you enjoyed Portland. Next time you have to make it to Boston! 🙂
I love Boston! It would be such a fun place for a girls weekend! The Samuel Adams Brewery was so fun. I also love wandering around the Boston Common and Public Gardens.
It really is a beautiful city! This recent trip was my second time in Boston and I fell in love with it even more! 🙂
I love it in Boston! My uncle moved there a few years ago so we have been to visit a few times! Such a beautiful and calm city
It really is a stunning city! I want to go back and see more. 🙂
oh my goodness that is SO cool you could see the Cheers bar! What a cool stop!
Yes, it was a fun place! Much bigger than I would’ve imagined though. 🙂
Boston has so many great breweries, and the Public Gardens are my favorite!
Yes, I loved them all, especially Cambridge! 🙂
These are some great places to visit in Boston for a weekend away! Adding some of these stops to my list for when I visit the city.
Yes, I love Boston so much! It is such a beautiful city! 🙂
I’ve been to Boston a couple of times but haven’t seen a lot of the places you posted! I will be saving this for my next trip out there!
It’s such a beautiful city! The things to do there are endless. 🙂
Boston is such a great city. I really want to go back again soon. Last time I was there was with my friend and it was an amazing girls trip. We did some of the touristy stuff but also just enjoyed checking out the city. I need to visit some of those breweries though. Next time for sure
Boston really is amazing! I feel like you definitely have to do the touristy stuff there. Also the food is great too! 🙂
What a fun blog! I do love Boston. Learned so much. I would love to stay at the old jail cell Hotel. Very cool concept. I also love history so would enjoy the Paul Revere House and Boston Harbor. Great foo recommendations too!
Thank you Ildiko! It sure was a lot of fun staying at the Liberty Hotel. 🙂
I love Boston! Such a fun city with so much history and is a great weekend getaway ant time of the year. The Liberty Hotel is such a great place to stay for its unique history and fun decor!
It really is a great city! The Liberty Hotel really is a lot of fun! 🙂
I LOVED this post! I’m dying to explore Boston and your article listed so many incredible places! Such a fun read.
Thank you Courtney! You totally have to go to Boston at some point. It is a beautiful city. 🙂