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Visiting the town of Washington Depot on a Gilmore Girls Connecticut Road Trip.

Connecticut is one of the most underrated destinations to visit during the holiday season in New England. Not only is The Constitution State famous for its exclusive towns and charming coastal villages, delicious seafood, historic inns and proximity to New York and Boston, but Connecticut is also iconic for being the inspiration behind the setting for the early 2000s television series Gilmore Girls.

Gilmore Girls was created by Amy Sherman-Palladino and takes place in an idyllic fictional town called Stars Hollow, Connecticut. The show debuted in October 2000 on The WB and ran for seven seasons. Gilmore Girls moved to The CW during its final season, which ended in May 2007.

The TV show follows the lives of a thirty-something single mom, Lorelai Gilmore, and her teenage daughter, Rory Gilmore. The townspeople of Stars Hollow are a constant presence throughout the series, and you can visit all the famous filming landmarks during a road trip through Eastern Connecticut.

A woman at Hogan's Cider Mill in Connecticut during the holiday season.

Even though you can visit the Gilmore Girls locations anytime during the year, the holiday season is one of the most special due to all the small-town charm that will also transport you into a Hallmark Christmas film. In this article, discover the best places to visit on a Gilmore Girls Connecticut road trip.

**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 Connecticut, I stayed in New Haven at Hotel Marcel, which hosted me for two nights.


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Gilmore Girls Holiday Connecticut Road Trip

Where was Gilmore Girls Filmed?

A woman in Washington Depot, Connecticut on a Gilmore Girls trip.

Even though Gilmore Girls’ actual filming location was in Burbank, California, the show’s creator, Amy Sherman-Palladino, got the inspiration for the fictional town of Stars Hollow from the Connecticut villages of Washington Depot, New Milford, Litchfield and West Hartford.

Amy Sherman-Palladino spent three weeks at the beautiful Mayflower Inn in Washington Depot while she explored the region for Gilmore Girls. She explained that the entire area featured the small-town charm she imagined for Stars Hollow, Connecticut.

Since Amy spoke about how magical it was being stuck in a snowstorm during a visit to Washington, it inspired my friend Chantilly and I to make a road trip there during the month of December.

Where to Stay during a Gilmore Girls Connecticut Road Trip:

A woman at Hotel Marcel in New Haven.

Even though the Mayflower Inn is considered the famous Gilmore Girls hotel, it’s regarded as a luxury accommodation and expensive for many people to stay at.

Since Washington and the surrounding towns are established in a rural location, it’s harder to find accommodation. When doing a girl’s trip, I prefer staying in a city that boasts a lot of great hotels, renowned restaurants and fun activities.

New Haven is a fantastic city to base yourself in during a Connecticut road trip because it’s less than an hour outside Washington Depot and less than a half hour from stunning Christmas tree farms. It’s around an hour-and-a-half drive from New York City and two hours and 15 minutes from Boston.

The best hotel to stay at in New Haven, CT is Hotel Marcel, which is part of Hilton’s Tapestry Collection. It’s a sustainable luxury hotel situated right off Interstate 95 and near all the best restaurants, activities and landmarks in the city of New Haven.

Brutalist architecture from Hotel Marcel in New Haven, Connecticut.

Hotel Marcel opened in 2022 in the former Armstrong Rubber Company building in New Haven, which features Brutalist architecture and Bauhaus design. What’s great about staying at Hotel Marcel is that it’s the only hotel in the United States with zero carbon emissions.

The hotel got its name from Marcel Breuer, who was behind the architecture of the Armstrong Rubber Company, a premier tire production. The building was constructed in the 1960s and you can admire its restored light fixtures, furnishings, artwork, tiles and more.

The Bauhaus was an artistic movement that originated in Germany in the early 1900s, which included abstract, angular and geometric elements. Brutalism emerged in the 1950s and showcased unique shapes and heavy materials. Bauhaus is featured throughout Hotel Marcel’s interior, while the exterior has a stark Brutalist design.

Staying at Hotel Marcel in New Haven, Connecticut:

Coffee from Hotel Marcel in New Haven.

During our visit to Hotel Marcel, Chantilly and I stayed in the Deluxe Two Queens room, which boasted two cozy queen-sized beds, views of the New Haven harbor, which leads out to the Long Island Sound, a spacious bathroom, modern amenities and curated art prints.

Other rooms and suites to choose from at Hotel Marcel are the Lightwell King, Lightwell Two Doubles, Standard King, Standard Two Queens, Deluxe King, Corner King, King Suite Sofa Bed, Chairman Suite, Lightwell Two Doubles Accessible, Deluxe King Accessible, Deluxe Two Queens Accessible, Corner King Suite Accessible and Presidential Suite Accessible.

What’s great about staying at Hotel Marcel is that it’s all-electric, completely independent of fossil fuels. Heating and air conditioning, hot water, the kitchen, laundry, the elevator and the hotel shuttle are all run by electricity.

There are also 12 250 kw Level 3 electric vehicle chargers for Teslas and 12 7.2 kw Level 2 vehicle chargers on the property. The hotel also has over 1,000 solar panels.

Breakfast from BLDG at Hotel Marcel in New Haven, CT.

Additionally, nothing was better than getting fueled for the day at Hotel Marcel’s BLDG restaurant. It’s New Haven’s newest sustainable dining spot with incredible farm-to-table options and a great wine and craft cocktail selection. Chantilly and I enjoyed breakfast at BLDG during our two-day stay; everything was delicious!

Traveling to Connecticut for a Gilmore Girls Getaway:

Hogan's Cider Mill decorated festively for Christmas in Northern Connecticut.

There are numerous ways to travel to Connecticut to visit the real Stars Hollow and other charming Gilmore Girls villages and Christmas tree farms.

If you’re traveling from afar, booking a flight into Bradley International Airport in Hartford, Tweed New Haven Airport, LaGuardia Airport in New York City or Westchester County Airport in White Plains, NY is best. You can find affordable flights through Skyscanner.

The best way to get around Connecticut to see all the Gilmore Girls locations is by having your own vehicle. If you fly into Connecticut, it’s best to rent a car.

Fairview Tree Farm in Shelton, Connecticut during Christmas time.

Another way to get around Connecticut is by public transportation. The Amtrak train stops in larger towns and cities like Mystic, Hartford, New Haven, Stamford and Waterbury. The New Haven Line, which Metro-North runs, goes from Grand Central Station in New York City to Waterbury, Danbury and New Canaan. The Shore Line East train makes several stops along the coast!

Connecticut also has numerous bus and carpools, along with ferry services. Click here to learn more.

Since Connecticut offers a plethora of wonderful destinations to stop at on a USA or East Coast road trip, click here if you want to rent an RV for you and your family.

2-Day Gilmore Girls Connecticut Road Trip at Christmastime:

Day 1: See the Real-Life Stars Hollow in Connecticut

A woman on a Gilmore Girls trip in Connecticut.

For all my fellow Gilmore Girls fans asking themselves, “Where is Stars Hollow?” you must visit the below destinations in Litchfield County, Connecticut! What is great about the destinations on this road trip itinerary is that many of these cute small towns are not a long drive from each other.

Walk through Downtown New Milford: A Charming Gilmore Girls Town

The first Gilmore Girls town to visit in Connecticut is New Milford. It features the gazebo that inspired the one in Stars Hollow.

A woman at the famous Gilmore Girls gazebo in New Milford, Connecticut.

No matter which season you decide to visit New Milford, CT, the gazebo on the town green will be decked out. Since Chantilly and I visited during the holiday season, it was decorated festively and included a beautiful Christmas tree.

This small Connecticut town is worth strolling through. There are picturesque New England-style churches, clothing boutiques, coffee shops, a movie theater, numerous photo opportunities and more. Lovers Leap State Park, Harris Hill Farm and Housatonic River Brewing are just a short distance from New Milford.

Stopping at Park Lane Cider Mill during a Gilmore Girls Connecticut road trip during the holiday season.

Park Lane Cider Mill is an adorable cider mill to visit for warm apple cider, fresh local apples, baked goods as well as homemade jams and sauces. It was a hidden gem!

Adventure through the Gilmore Girls Town of Washington Depot: Stars Hollow Inspiration

The ultimate Gilmore Girls location, where all the famous landmarks from the series were inspired, is in Washington Depot, CT. Here, you’ll spend the most time during your 2-day road trip through Connecticut. Even though Washington is a tiny town, there are a lot of charming spots you cannot miss out on visiting.

The Mayflower Inn

The first destination you must visit in the rural town of Washington is the Mayflower Inn. This luxury boutique hotel by Auberge Resort Collection is a cozy inn with an incredible spa, gardens, farm-to-table restaurant and event venue.

The Mayflower Inn is where Amy Sherman-Palladino stayed and got the inspiration for Stars Hollow’s Independence Inn. Reserve a room at the Mayflower Inn, book a spa day or enjoy the onsite restaurant.

The Hickory Stick Bookshop in Washington Depot, CT.

As you make your way into the Depot, you can visit The Hickory Stick Bookshop, which was the inspiration for Stars Hollow Books. While at The Hickory Stick Bookshop, there is an entire Gilmore Girls section with a Rory Reads List, where you can participate in a book challenge. Stars Hollow Books was also where Rory spent a lot of time shopping for new reads and volunteering.

The Gilmore Girls-inspired hardware store in Washington Depot, Connecticut during the holidays.

Across the street from The Hickory Stick Bookshop is the Washington Supply Company, the inspiration behind the hardware store featured in the show. In fact, Luke’s Diner from Gilmore Girls, inspired by Marty’s Café in Washington Depot, was situated inside Williams Hardware in the show. Even though Marty’s Café is in the building next to Washington Supply Company, it was where Amy got the idea for Luke’s.

Even though Marty’s Café looks nothing like Luke’s Diner in the television series, it’s the social atmosphere from which Amy Sherman-Palladino got its vision. If you’re looking for a café with an aesthetic similar to Luke’s, you must visit The Po Café on Route 47 before passing the big white church on Kirby Road.

A woman enjoying coffee and a treat at Marty's Cafe in Connecticut, which was the inspiration of Luke's Diner in Gilmore Girls.

Marty’s Café is a charming coffee shop where you can grab a specialty latte, baked treat and savory lunch. It boasts a cozy and peaceful atmosphere perfect for relaxing, catching up with a friend and getting work done!

The Pantry is another great eatery like Weston’s in Gilmore Girls. It was where Lorelai and Rory would go when they were mad at Luke Danes (who owned Luke’s Diner).

Also located in the town square is the Washington Town Hall, which resembles the Stars Hollow Court House, where weekly town meetings would occur. Across from the Bryan Memorial Town Hall is Washington Food Market, where Amy Sherman-Palladino got the inspiration for Doose’s Market, where Lorelai and Rory would purchase groceries.

Washington Depot's Bryan Memorial Town Hall.

Next door to Washington Food Market is Five Janes, an adorable gift shop with awesome Stars Hollow merchandise. It’s a fun place to stop on a Gilmore Girls Connecticut road trip!

Go Shopping in Litchfield:

The next stop on a Gilmore Girls trip is to the idyllic town of Litchfield, CT. Fans of the show can visit Arethusa Farm for an incredible meal. (During the summer of 2023, Martha Stewart filmed her “Martha Cooks” show at this location.)

Visiting Arethusa Farm in during a Gilmore Girls Connecticut road trip.

At Arethusa Farm Dairy in Bantam and New Haven, you can enjoy homemade ice cream that rivals Taylor’s Soda Shoppe in the series. (Taylor Doose owned the old-fashioned soda shop and food market in Gilmore Girls.)

The charming downtown of Litchfield, Connecticut.

The charming town of Litchfield is also worth walking around. It’s popular for its antique stores, lovely restaurants, coffee shops and Hallmark Christmas movie vibes.

Enjoy the Festive Hogan’s Cider Mill:

A woman at Hogan's Cider Mill during the Christmas season.

One of the best places to visit during a Connecticut road trip during Christmastime that has nothing to do with Gilmore Girls is Hogan’s Cider Mill in the small town of Burlington.

This cider mill is iconic in Northeastern Connecticut and reminded me of what you’d see in a Hallmark Christmas movie. Whether you visit Hogan’s Cider Mill during autumn or the holiday season, you will love its charming decorations.

Hogan’s Cider Mill has existed since 1912 when Patrick Hogan, the son of Irish immigrants, started the production of apple cider. Nowadays, it’s a New England icon and one of the most festive places in Connecticut.

The holiday cider from Hogan's Cider Mill in Connecticut.

During December, you can shop for magical décor and home goods and visit the onsite tap room to enjoy seasonal hard cider, non-alcoholic mulled cider and Hogan’s festive Jolly Drunken Donut. This fun holiday drink blends pressed sweet cider and mulled spices, is spiked with December Frost Hard Cider, and served with a cider donut, whipped cream and sprinkles.

Ride the Christmas Train in Thomaston:

Thomaston is another quaint town you must visit during your Connecticut Gilmore Girls road trip. Even though there aren’t any Gilmore Girls-inspired locations in Thomaston, it will still transport you into a Hallmark Christmas film or, better yet, the North Pole through a Polar Express-like experience!

Located in the heart of Thomaston is the Railroad Museum of New England. This non-profit historic organization tells the story of the region’s rich railroad heritage through memorable train rides.

The Christmas train at The Railroad Museum of New England.

During the Christmas season, you can book a festive train ride that is fun for all ages. The Northern Lights Limited is an evening train ride where you and your family can enjoy illuminated train carts, visit Santa’s Workshop and dance to Christmas jams. The Santa Express is an afternoon train ride for young children where Santa and his Elves visit passengers.

For adults 21 and older looking to have a festive experience with friends, a significant other, or even family, the Holiday Spirits – Sippin’ with Santa train ride is a 3-hour journey where you can enjoy drinks with Santa from local breweries, wineries and distilleries. There are also chocolate pairings, fun giveaways and tasty bites.

The Railroad Museum of New England also hosts an Autism-Friendly Santa Express, with sensory considerations and a Toys for Tots Train.

Afterward, walk around Thomaston and stop at one of the restaurants in town, like Black Rock Tavern & Restaurant.

Day 2: Explore New Haven and Connecticut Christmas Tree Farms

A woman at Jones Family Farm in Shelton, Connecticut.

As you travel around Connecticut during the holiday season to see the famous Gilmore Girls locations, you must also explore the city of New Haven and its nearby Christmas tree farms. They are magical!

Check Out Yale University’s Campus:

Yale University campus.

While you stay at Hotel Marcel in New Haven, you must visit Yale University. It’s a private Ivy League university that was founded in 1701.

Since Yale is the third-oldest university in the United States, you can visit and take a tour led by college students. During the tour, you’ll learn about Yale’s 300-year history and see the beautiful Gothic Sterling Memorial Library, one of the most iconic buildings on campus.

Visiting Yale University will transport you to a real-life Hogwarts with its medieval architecture and Harry Potter vibes.

Savor New Haven Pizza:

Pizza and wine from Frank Pepe in New Haven, CT.

A trip to Connecticut is incomplete without savoring delicious New Haven-style pizza, which consists of a thin crust and is coal-fired.

While you’re in New Haven, CT you must visit the city’s Little Italy neighborhood and eat at some of the most iconic pizza restaurants like Frank Pepe Pizzeria Napoletana, Sally’s Apizza and Modern Apizza.

Since I had heard about Frank Pepe numerous times before my Gilmore Girls Connecticut trip, I just had to go there! This iconic spot is also home to the Original White Clam Pizza, so I also had to order that.

What I loved about visiting Frank Pepe Pizzeria Napoletana was that it featured the old-school, laid-back and cozy pizzeria ambiance that is hard to come by nowadays. Also, you can’t beat the prices at Frank Pepe!

Because Frank Pepe Pizzeria Napoletana is popular, you may have to wait in line before being able to enter and get seated. Don’t let that turn you off, though; the pizzeria is efficient and the line goes fast.

Spend an Afternoon at Jones Family Farms:

Jones Family Farm during Christmas.

A half-hour from New Haven is a Hallmark Christmas-type town called Shelton, home to some of the most picture-perfect tree farms.

During a December Connecticut road trip, you must visit Jones Family Farms. From the moment you arrive, you will be greeted with a warm welcome from the farm’s festive ambiance. There is a beautiful selection of Christmas trees, wreaths and garlands to purchase, cozy fire pits to warm up and music to get you and your loved ones in the holiday spirit.

When you visit Jones Family Farms during autumn or the holiday season, you can also go to the winery, where you can do a tasting and warm up with mulled wine or cider.

There’s also The Harvest Kitchen, where you can purchase food and savor it in the onsite gazebo that overlooks the vineyards. Don’t forget to buy homemade jam and farm-fresh cheeses at this spot.

Chantilly and I were lucky to visit Jones Family Farms while snow was flurrying and it was pure magic!

Visit Fairview Tree Farm:

A woman at Fairview Tree Farm during Christmas.

Located down the road from Jones Family Farms is Fairview Tree Farm, which is perfect for those with little ones.

Not only are there countless spots for Christmas card photo opportunities and the ability to choose and cut down your own tree, but you and your family can also enjoy horse-drawn hayrides during the holiday season. There are daytime hayrides, tractor hayrides with Santa and the Nights of Lights Merry Christmas Hayride.

Even though you don’t need a reservation to cut your own tree, you’ll need to reserve your spot for one of the hayrides in advance. Click here to learn more.

This farm is also great to visit during the fall. Remember to say hi to the adorable farm animals at Fairview Tree Farm!


Fairview Tree Farm during a snowstorm.

Loved the holiday vibes of these Connecticut locations? You’ll also enjoy visiting the below destinations:

Cape May, New Jersey

Finger Lakes, New York

Natchitoches, Louisiana

I hope you all enjoyed discovering the best places to visit on a Gilmore Girls Connecticut road trip. If you have any questions, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., CT State Capital: Hartford, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Connecticut Christmas Look:

Click here to shop my Poshmark closet!

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2 Comments

  1. Kim Deer on December 21, 2023 at 12:09 am

    What a fun blog and such beautiful quaint towns in Connecticut! Great time of the year to visit these fun filled Gilmore Girl’s locations. Loved the old fashioned trucks, the Christmas tree farms and delicious farm markets! Enjoyed reading how these areas inspired Amy Sherman Palladino to write the Gilmore Girls TV series. Awesome read ~ love you, mom 👩🏻 xoxo ❤️

    • Taylor Deer on December 27, 2023 at 10:08 am

      Thank you mom! It was very quintessential!

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Taylor-New-Milford1

Visiting the town of Washington Depot on a Gilmore Girls Connecticut Road Trip.

Connecticut is one of the most underrated destinations to visit during the holiday season in New England. Not only is The Constitution State famous for its exclusive towns and charming coastal villages, delicious seafood, historic inns and proximity to New York and Boston, but Connecticut is also iconic for being the inspiration behind the setting for the early 2000s television series Gilmore Girls.

Gilmore Girls was created by Amy Sherman-Palladino and takes place in an idyllic fictional town called Stars Hollow, Connecticut. The show debuted in October 2000 on The WB and ran for seven seasons. Gilmore Girls moved to The CW during its final season, which ended in May 2007.

The TV show follows the lives of a thirty-something single mom, Lorelai Gilmore, and her teenage daughter, Rory Gilmore. The townspeople of Stars Hollow are a constant presence throughout the series, and you can visit all the famous filming landmarks during a road trip through Eastern Connecticut.

A woman at Hogan's Cider Mill in Connecticut during the holiday season.

Even though you can visit the Gilmore Girls locations anytime during the year, the holiday season is one of the most special due to all the small-town charm that will also transport you into a Hallmark Christmas film. In this article, discover the best places to visit on a Gilmore Girls Connecticut road trip.

**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 Connecticut, I stayed in New Haven at Hotel Marcel, which hosted me for two nights.


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Gilmore Girls Holiday Connecticut Road Trip

Where was Gilmore Girls Filmed?

A woman in Washington Depot, Connecticut on a Gilmore Girls trip.

Even though Gilmore Girls’ actual filming location was in Burbank, California, the show’s creator, Amy Sherman-Palladino, got the inspiration for the fictional town of Stars Hollow from the Connecticut villages of Washington Depot, New Milford, Litchfield and West Hartford.

Amy Sherman-Palladino spent three weeks at the beautiful Mayflower Inn in Washington Depot while she explored the region for Gilmore Girls. She explained that the entire area featured the small-town charm she imagined for Stars Hollow, Connecticut.

Since Amy spoke about how magical it was being stuck in a snowstorm during a visit to Washington, it inspired my friend Chantilly and I to make a road trip there during the month of December.

Where to Stay during a Gilmore Girls Connecticut Road Trip:

A woman at Hotel Marcel in New Haven.

Even though the Mayflower Inn is considered the famous Gilmore Girls hotel, it’s regarded as a luxury accommodation and expensive for many people to stay at.

Since Washington and the surrounding towns are established in a rural location, it’s harder to find accommodation. When doing a girl’s trip, I prefer staying in a city that boasts a lot of great hotels, renowned restaurants and fun activities.

New Haven is a fantastic city to base yourself in during a Connecticut road trip because it’s less than an hour outside Washington Depot and less than a half hour from stunning Christmas tree farms. It’s around an hour-and-a-half drive from New York City and two hours and 15 minutes from Boston.

The best hotel to stay at in New Haven, CT is Hotel Marcel, which is part of Hilton’s Tapestry Collection. It’s a sustainable luxury hotel situated right off Interstate 95 and near all the best restaurants, activities and landmarks in the city of New Haven.

Brutalist architecture from Hotel Marcel in New Haven, Connecticut.

Hotel Marcel opened in 2022 in the former Armstrong Rubber Company building in New Haven, which features Brutalist architecture and Bauhaus design. What’s great about staying at Hotel Marcel is that it’s the only hotel in the United States with zero carbon emissions.

The hotel got its name from Marcel Breuer, who was behind the architecture of the Armstrong Rubber Company, a premier tire production. The building was constructed in the 1960s and you can admire its restored light fixtures, furnishings, artwork, tiles and more.

The Bauhaus was an artistic movement that originated in Germany in the early 1900s, which included abstract, angular and geometric elements. Brutalism emerged in the 1950s and showcased unique shapes and heavy materials. Bauhaus is featured throughout Hotel Marcel’s interior, while the exterior has a stark Brutalist design.

Staying at Hotel Marcel in New Haven, Connecticut:

Coffee from Hotel Marcel in New Haven.

During our visit to Hotel Marcel, Chantilly and I stayed in the Deluxe Two Queens room, which boasted two cozy queen-sized beds, views of the New Haven harbor, which leads out to the Long Island Sound, a spacious bathroom, modern amenities and curated art prints.

Other rooms and suites to choose from at Hotel Marcel are the Lightwell King, Lightwell Two Doubles, Standard King, Standard Two Queens, Deluxe King, Corner King, King Suite Sofa Bed, Chairman Suite, Lightwell Two Doubles Accessible, Deluxe King Accessible, Deluxe Two Queens Accessible, Corner King Suite Accessible and Presidential Suite Accessible.

What’s great about staying at Hotel Marcel is that it’s all-electric, completely independent of fossil fuels. Heating and air conditioning, hot water, the kitchen, laundry, the elevator and the hotel shuttle are all run by electricity.

There are also 12 250 kw Level 3 electric vehicle chargers for Teslas and 12 7.2 kw Level 2 vehicle chargers on the property. The hotel also has over 1,000 solar panels.

Breakfast from BLDG at Hotel Marcel in New Haven, CT.

Additionally, nothing was better than getting fueled for the day at Hotel Marcel’s BLDG restaurant. It’s New Haven’s newest sustainable dining spot with incredible farm-to-table options and a great wine and craft cocktail selection. Chantilly and I enjoyed breakfast at BLDG during our two-day stay; everything was delicious!

Traveling to Connecticut for a Gilmore Girls Getaway:

Hogan's Cider Mill decorated festively for Christmas in Northern Connecticut.

There are numerous ways to travel to Connecticut to visit the real Stars Hollow and other charming Gilmore Girls villages and Christmas tree farms.

If you’re traveling from afar, booking a flight into Bradley International Airport in Hartford, Tweed New Haven Airport, LaGuardia Airport in New York City or Westchester County Airport in White Plains, NY is best. You can find affordable flights through Skyscanner.

The best way to get around Connecticut to see all the Gilmore Girls locations is by having your own vehicle. If you fly into Connecticut, it’s best to rent a car.

Fairview Tree Farm in Shelton, Connecticut during Christmas time.

Another way to get around Connecticut is by public transportation. The Amtrak train stops in larger towns and cities like Mystic, Hartford, New Haven, Stamford and Waterbury. The New Haven Line, which Metro-North runs, goes from Grand Central Station in New York City to Waterbury, Danbury and New Canaan. The Shore Line East train makes several stops along the coast!

Connecticut also has numerous bus and carpools, along with ferry services. Click here to learn more.

Since Connecticut offers a plethora of wonderful destinations to stop at on a USA or East Coast road trip, click here if you want to rent an RV for you and your family.

2-Day Gilmore Girls Connecticut Road Trip at Christmastime:

Day 1: See the Real-Life Stars Hollow in Connecticut

A woman on a Gilmore Girls trip in Connecticut.

For all my fellow Gilmore Girls fans asking themselves, “Where is Stars Hollow?” you must visit the below destinations in Litchfield County, Connecticut! What is great about the destinations on this road trip itinerary is that many of these cute small towns are not a long drive from each other.

Walk through Downtown New Milford: A Charming Gilmore Girls Town

The first Gilmore Girls town to visit in Connecticut is New Milford. It features the gazebo that inspired the one in Stars Hollow.

A woman at the famous Gilmore Girls gazebo in New Milford, Connecticut.

No matter which season you decide to visit New Milford, CT, the gazebo on the town green will be decked out. Since Chantilly and I visited during the holiday season, it was decorated festively and included a beautiful Christmas tree.

This small Connecticut town is worth strolling through. There are picturesque New England-style churches, clothing boutiques, coffee shops, a movie theater, numerous photo opportunities and more. Lovers Leap State Park, Harris Hill Farm and Housatonic River Brewing are just a short distance from New Milford.

Stopping at Park Lane Cider Mill during a Gilmore Girls Connecticut road trip during the holiday season.

Park Lane Cider Mill is an adorable cider mill to visit for warm apple cider, fresh local apples, baked goods as well as homemade jams and sauces. It was a hidden gem!

Adventure through the Gilmore Girls Town of Washington Depot: Stars Hollow Inspiration

The ultimate Gilmore Girls location, where all the famous landmarks from the series were inspired, is in Washington Depot, CT. Here, you’ll spend the most time during your 2-day road trip through Connecticut. Even though Washington is a tiny town, there are a lot of charming spots you cannot miss out on visiting.

The Mayflower Inn

The first destination you must visit in the rural town of Washington is the Mayflower Inn. This luxury boutique hotel by Auberge Resort Collection is a cozy inn with an incredible spa, gardens, farm-to-table restaurant and event venue.

The Mayflower Inn is where Amy Sherman-Palladino stayed and got the inspiration for Stars Hollow’s Independence Inn. Reserve a room at the Mayflower Inn, book a spa day or enjoy the onsite restaurant.

The Hickory Stick Bookshop in Washington Depot, CT.

As you make your way into the Depot, you can visit The Hickory Stick Bookshop, which was the inspiration for Stars Hollow Books. While at The Hickory Stick Bookshop, there is an entire Gilmore Girls section with a Rory Reads List, where you can participate in a book challenge. Stars Hollow Books was also where Rory spent a lot of time shopping for new reads and volunteering.

The Gilmore Girls-inspired hardware store in Washington Depot, Connecticut during the holidays.

Across the street from The Hickory Stick Bookshop is the Washington Supply Company, the inspiration behind the hardware store featured in the show. In fact, Luke’s Diner from Gilmore Girls, inspired by Marty’s Café in Washington Depot, was situated inside Williams Hardware in the show. Even though Marty’s Café is in the building next to Washington Supply Company, it was where Amy got the idea for Luke’s.

Even though Marty’s Café looks nothing like Luke’s Diner in the television series, it’s the social atmosphere from which Amy Sherman-Palladino got its vision. If you’re looking for a café with an aesthetic similar to Luke’s, you must visit The Po Café on Route 47 before passing the big white church on Kirby Road.

A woman enjoying coffee and a treat at Marty's Cafe in Connecticut, which was the inspiration of Luke's Diner in Gilmore Girls.

Marty’s Café is a charming coffee shop where you can grab a specialty latte, baked treat and savory lunch. It boasts a cozy and peaceful atmosphere perfect for relaxing, catching up with a friend and getting work done!

The Pantry is another great eatery like Weston’s in Gilmore Girls. It was where Lorelai and Rory would go when they were mad at Luke Danes (who owned Luke’s Diner).

Also located in the town square is the Washington Town Hall, which resembles the Stars Hollow Court House, where weekly town meetings would occur. Across from the Bryan Memorial Town Hall is Washington Food Market, where Amy Sherman-Palladino got the inspiration for Doose’s Market, where Lorelai and Rory would purchase groceries.

Washington Depot's Bryan Memorial Town Hall.

Next door to Washington Food Market is Five Janes, an adorable gift shop with awesome Stars Hollow merchandise. It’s a fun place to stop on a Gilmore Girls Connecticut road trip!

Go Shopping in Litchfield:

The next stop on a Gilmore Girls trip is to the idyllic town of Litchfield, CT. Fans of the show can visit Arethusa Farm for an incredible meal. (During the summer of 2023, Martha Stewart filmed her “Martha Cooks” show at this location.)

Visiting Arethusa Farm in during a Gilmore Girls Connecticut road trip.

At Arethusa Farm Dairy in Bantam and New Haven, you can enjoy homemade ice cream that rivals Taylor’s Soda Shoppe in the series. (Taylor Doose owned the old-fashioned soda shop and food market in Gilmore Girls.)

The charming downtown of Litchfield, Connecticut.

The charming town of Litchfield is also worth walking around. It’s popular for its antique stores, lovely restaurants, coffee shops and Hallmark Christmas movie vibes.

Enjoy the Festive Hogan’s Cider Mill:

A woman at Hogan's Cider Mill during the Christmas season.

One of the best places to visit during a Connecticut road trip during Christmastime that has nothing to do with Gilmore Girls is Hogan’s Cider Mill in the small town of Burlington.

This cider mill is iconic in Northeastern Connecticut and reminded me of what you’d see in a Hallmark Christmas movie. Whether you visit Hogan’s Cider Mill during autumn or the holiday season, you will love its charming decorations.

Hogan’s Cider Mill has existed since 1912 when Patrick Hogan, the son of Irish immigrants, started the production of apple cider. Nowadays, it’s a New England icon and one of the most festive places in Connecticut.

The holiday cider from Hogan's Cider Mill in Connecticut.

During December, you can shop for magical décor and home goods and visit the onsite tap room to enjoy seasonal hard cider, non-alcoholic mulled cider and Hogan’s festive Jolly Drunken Donut. This fun holiday drink blends pressed sweet cider and mulled spices, is spiked with December Frost Hard Cider, and served with a cider donut, whipped cream and sprinkles.

Ride the Christmas Train in Thomaston:

Thomaston is another quaint town you must visit during your Connecticut Gilmore Girls road trip. Even though there aren’t any Gilmore Girls-inspired locations in Thomaston, it will still transport you into a Hallmark Christmas film or, better yet, the North Pole through a Polar Express-like experience!

Located in the heart of Thomaston is the Railroad Museum of New England. This non-profit historic organization tells the story of the region’s rich railroad heritage through memorable train rides.

The Christmas train at The Railroad Museum of New England.

During the Christmas season, you can book a festive train ride that is fun for all ages. The Northern Lights Limited is an evening train ride where you and your family can enjoy illuminated train carts, visit Santa’s Workshop and dance to Christmas jams. The Santa Express is an afternoon train ride for young children where Santa and his Elves visit passengers.

For adults 21 and older looking to have a festive experience with friends, a significant other, or even family, the Holiday Spirits – Sippin’ with Santa train ride is a 3-hour journey where you can enjoy drinks with Santa from local breweries, wineries and distilleries. There are also chocolate pairings, fun giveaways and tasty bites.

The Railroad Museum of New England also hosts an Autism-Friendly Santa Express, with sensory considerations and a Toys for Tots Train.

Afterward, walk around Thomaston and stop at one of the restaurants in town, like Black Rock Tavern & Restaurant.

Day 2: Explore New Haven and Connecticut Christmas Tree Farms

A woman at Jones Family Farm in Shelton, Connecticut.

As you travel around Connecticut during the holiday season to see the famous Gilmore Girls locations, you must also explore the city of New Haven and its nearby Christmas tree farms. They are magical!

Check Out Yale University’s Campus:

Yale University campus.

While you stay at Hotel Marcel in New Haven, you must visit Yale University. It’s a private Ivy League university that was founded in 1701.

Since Yale is the third-oldest university in the United States, you can visit and take a tour led by college students. During the tour, you’ll learn about Yale’s 300-year history and see the beautiful Gothic Sterling Memorial Library, one of the most iconic buildings on campus.

Visiting Yale University will transport you to a real-life Hogwarts with its medieval architecture and Harry Potter vibes.

Savor New Haven Pizza:

Pizza and wine from Frank Pepe in New Haven, CT.

A trip to Connecticut is incomplete without savoring delicious New Haven-style pizza, which consists of a thin crust and is coal-fired.

While you’re in New Haven, CT you must visit the city’s Little Italy neighborhood and eat at some of the most iconic pizza restaurants like Frank Pepe Pizzeria Napoletana, Sally’s Apizza and Modern Apizza.

Since I had heard about Frank Pepe numerous times before my Gilmore Girls Connecticut trip, I just had to go there! This iconic spot is also home to the Original White Clam Pizza, so I also had to order that.

What I loved about visiting Frank Pepe Pizzeria Napoletana was that it featured the old-school, laid-back and cozy pizzeria ambiance that is hard to come by nowadays. Also, you can’t beat the prices at Frank Pepe!

Because Frank Pepe Pizzeria Napoletana is popular, you may have to wait in line before being able to enter and get seated. Don’t let that turn you off, though; the pizzeria is efficient and the line goes fast.

Spend an Afternoon at Jones Family Farms:

Jones Family Farm during Christmas.

A half-hour from New Haven is a Hallmark Christmas-type town called Shelton, home to some of the most picture-perfect tree farms.

During a December Connecticut road trip, you must visit Jones Family Farms. From the moment you arrive, you will be greeted with a warm welcome from the farm’s festive ambiance. There is a beautiful selection of Christmas trees, wreaths and garlands to purchase, cozy fire pits to warm up and music to get you and your loved ones in the holiday spirit.

When you visit Jones Family Farms during autumn or the holiday season, you can also go to the winery, where you can do a tasting and warm up with mulled wine or cider.

There’s also The Harvest Kitchen, where you can purchase food and savor it in the onsite gazebo that overlooks the vineyards. Don’t forget to buy homemade jam and farm-fresh cheeses at this spot.

Chantilly and I were lucky to visit Jones Family Farms while snow was flurrying and it was pure magic!

Visit Fairview Tree Farm:

A woman at Fairview Tree Farm during Christmas.

Located down the road from Jones Family Farms is Fairview Tree Farm, which is perfect for those with little ones.

Not only are there countless spots for Christmas card photo opportunities and the ability to choose and cut down your own tree, but you and your family can also enjoy horse-drawn hayrides during the holiday season. There are daytime hayrides, tractor hayrides with Santa and the Nights of Lights Merry Christmas Hayride.

Even though you don’t need a reservation to cut your own tree, you’ll need to reserve your spot for one of the hayrides in advance. Click here to learn more.

This farm is also great to visit during the fall. Remember to say hi to the adorable farm animals at Fairview Tree Farm!


Fairview Tree Farm during a snowstorm.

Loved the holiday vibes of these Connecticut locations? You’ll also enjoy visiting the below destinations:

Cape May, New Jersey

Finger Lakes, New York

Natchitoches, Louisiana

I hope you all enjoyed discovering the best places to visit on a Gilmore Girls Connecticut road trip. If you have any questions, please email me at info@browneyedflowerchild.com.

Basic Facts of the United States:

Currency: United States Dollar, Capital: Washington D.C., CT State Capital: Hartford, Time Zone: Eastern Standard Time

*Anything could happen during your travels. Always make sure you are insured in case there are unforeseen circumstances such as lost luggage/theft, natural disasters, personal liabilities and more. Click here to get insured for your next trip.

Shop my Connecticut Christmas Look:

Click here to shop my Poshmark closet!

2 Comments

  1. Kim Deer on December 21, 2023 at 12:09 am

    What a fun blog and such beautiful quaint towns in Connecticut! Great time of the year to visit these fun filled Gilmore Girl’s locations. Loved the old fashioned trucks, the Christmas tree farms and delicious farm markets! Enjoyed reading how these areas inspired Amy Sherman Palladino to write the Gilmore Girls TV series. Awesome read ~ love you, mom 👩🏻 xoxo ❤️

    • Taylor Deer on December 27, 2023 at 10:08 am

      Thank you mom! It was very quintessential!

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