The Berkshires of Western Massachusetts is a special place to spend a summer weekend in the mountains. Even though there are a plethora of charming villages and towns to explore in this area, Pittsfield, Massachusetts is the best spot to enjoy summer activities in the Berkshires.

Located in the heart of the Berkshires, Pittsfield is the largest city in Western Massachusetts and it’s home to award-winning restaurants, world-class performance venues, fascinating historic properties, great retail shops, a vibrant music and art scene, plus incredible outdoor recreation.

During July 2022, I visited Pittsfield, Massachusetts with the tourism board and a few other travel bloggers. We stayed two nights in the luxury boutique Hotel on North, which is in Downtown Pittsfield and had fun experiencing the city’s dining and art scene along with exploring local hiking and nature trails.

Whether you are exploring the Berkshires on a New England road trip or are enjoying a summer weekend getaway from New York City or Boston, there are so many great things to do for everyone to enjoy.

**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. My summer trip to the Berkshires was in partnership with Pittsfield, Massachusetts.

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Traveling to the Berkshires for a Summer Getaway Weekend:

When it comes to traveling to Western Massachusetts to enjoy summer weekend activities, you can either take a flight or drive. The closest international airport to the Berkshires is Albany International Airport. You can find affordable flights through Skyscanner.

Another way to experience a Berkshires weekend is by driving! Since I traveled from Northern New Jersey to New England, I drove my own car. It took me around two and a half hours to drive from my home in New Jersey to Pittsfield.

Whether you decide to take your own car or catch a flight to enjoy summer in the Berkshires, you will need a vehicle to get around. For those flying, I recommend renting a car from the airport.

If you don’t have your own car, it is best to get around to all the Berkshire towns by taking the Berkshire Regional Transit Authority buses. Amtrak also goes into the Pittsfield train station at Joseph Scelsi Intermodal Transportation Center. The Berkshire Flyer is run through Amtrak and it offers seasonal weekend service to and from New York’s Moynihan Station. It’s the best way to enjoy scenic views of New York’s Catskills and the Berkshire mountains!

Where to Stay in the Berkshires:

Situated in the heart of Downtown Pittsfield, Hotel on North is the best place to stay during a summer weekend in the Berkshires. It is a 45-room luxury boutique hotel that celebrates art! Each room has a different character and is cozy and welcoming.

Staying at Hotel on North in Pittsfield:

Overall, I loved how Hotel on North is close to so many great restaurants and shops in Pittsfield, Massachusetts. It was nice to be able to walk to breakfast and dinner every day and to the Barrington Stage for a show one evening.

Also located inside of Hotel on North is Berkshire Palate where you can enjoy craft food and drinks. It’s a cozy spot where you can sip cocktails in a birdcage elevator or enjoy board games with wine on one of the cozy couches. Regarding food at Berkshire Palate, you can choose from charcuterie boards to flatbreads and small plates to burgers. There is also a summer farm harvest section to Berkshire Palate’s menu that feature locally sourced summer ingredients.

I adore the rooms at Hotel on North! Each hotel room boasts locally crafted, handpicked furniture and décor that draws out the distinctive character of Cultural Pittsfield. During my two nights at this lovely hotel, I stayed in the Standard double queen room, since my friend was with me.

My room had two big windows that overlooked Downtown Pittsfield. I loved how cozy it was and the en-suite bathroom was spacious! In addition to the Standard rooms, Hotel on North also has Superior rooms for four guests; Premier rooms for two guests; Premier rooms with a fireplace for two guests; Premier Extended Stay rooms for two guests, which are like an apartment, and the Library Suite (for up to four guests) that boasts 125 bookshelves filled with curated books, crafts, memorabilia and design pieces.

Even though I didn’t stay in the Library Suite, I got to tour it and the entire room made me feel like I was Belle from Beauty and the Beast.

In addition to the restaurant and rooms, Hotel on North also has event spaces for corporate meetings, weddings and other special events.

Best Places to Go in the Berkshires for Good Food:

The Berkshires is known for its culinary scene and during a summer weekend in Pittsfield, you will not go wrong with any restaurant or café that you visit.

Below are my favorite spots to eat in the Berkshires during summer:

Mission: This rustic-chic tapas and wine bar offers a laid-back vibe with seasonal small plates. What I loved about Mission Restaurant was that they also offered live music to enjoy while you had your dinner and drinks.

During my time at Mission, I was with a group of people and we shared a bunch of appetizers to start the evening off with. We got the New England cheese board, roasted beetroot and burrata salad and crispy fried brussels sprouts. For my main meal, I had the roasted chicken breast and it was delicious!

Dottie’s Coffee Lounge: A great spot to have breakfast during a summer morning in Pittsfield is at Dottie’s Coffee Lounge as it offers outdoor seating. It is an upbeat coffee shop that features locally sourced breakfast menu items like burrito bowls, bagels and pastries.

During my breakfast at Dottie’s, I had the oatmeal with Bear Butter, which is a staple to this area. It’s a blend of almond butter, vegan vanilla protein, cacao nibs, goji berries, hemp seeds, flax seeds and coconut flakes. It’s delicious, filling and perfect with a nice latte.

Dottie’s also participates in the Oats 4 All Project – Buy One, Give One. When you get oatmeal for breakfast, you’re also providing one for someone in the community.

Marketplace Café: This health café is the perfect lunch spot to enjoy gourmet sandwiches, salads, soups, paninis and freshly baked treats (it’s known for its lemon bars too). They also offer great coffee along with vegan and gluten-free options.

What is also awesome about Marketplace Café is that they make it easy to take their items to go. When our group had a picnic at Pittsfield State Forest, we catered from Marketplace Café and it was perfect! I enjoyed the Stockbridge Bowl, which consisted of arugula, kale, quinoa, edamame, pickled vegetables and extra virgin olive oil.

King Kone: There is nothing like enjoying an ice cream cone during a hot summer day. One of the best things to do in the Berkshires in the summer during a weekend getaway is to enjoy some soft serve at King Kone.

Overall, King Kone is a staple to Pittsfield, Massachusetts. A fun fact is that actress Elizabeth Banks was born in this charming Berkshires town and always raves about this awesome ice cream shop.

King Kone gives you a lot of ice cream and when you buy a cone, it will get messy! I recommend not wearing a nice outfit like I did when you get this incredible soft serve ice cream because it does melt quick on a hot summer day. It’s delicious though and you must include visiting this spot in your Berkshires itinerary!

District Kitchen & Bar: A swanky American restaurant that features an intimate vibe is District Kitchen & Bar. It offers a seasonal menu with craft cocktails.

During my evening at this lovely restaurant, our group shared a bunch of appetizers. We ordered the truffle fries, grilled asparagus, grilled calamari and cheeseboard. For my main meal, I enjoyed the grilled swordfish and Mediterranean couscous. Everything was tasty!

Otto’s Kitchen & Comfort: Another awesome breakfast spot to enjoy in Pittsfield during a summer weekend in the Berkshires is Otto’s Kitchen & Comfort. It’s a typical American breakfast spot that offers everything from egg dishes to pancakes and hash browns to bacon. There is something for everyone to enjoy at Otto’s.

When I had breakfast at Otto’s, I savored the Belgian waffle with fresh strawberries and whipped cream. I also had bacon on the side with a coffee. Sometimes a simple American breakfast like this truly hits the spot!

Bimi’s Café at Hancock Shaker Village: In addition to a cheese shop location in Chatham, New York, Bimi’s also has a café at the Hancock Shaker Village in Pittsfield, Massachusetts and you must go during your Berkshires vacation.

During our group’s visit to Hancock Shaker Village, we had lunch at Bimi’s Café and it was amazing! I loved all of the incredible sandwich and panini options. They also had a variety of great kombuchas, craft beers, hard seltzers, canned wine, coffee, hot chocolate and more at this great spot.

For lunch, I had the Caprese panini with a kombucha and it was incredible.

Methuselah Bar and Lounge: My favorite bar in Pittsfield, Massachusetts, that you must visit during a Berkshires getaway weekend, is Methuselah Bar. It is a rustic-chic and trendy cocktail lounge that has stringed lights hanging throughout the entire bar.

To me, this is the perfect date night spot in Pittsfield and it’s also a great place to go during a girls trip to the Berkshires. You can enjoy everything from mezcals to craft beer and local wine to spirits.

Things to do in the Berkshires in the Summer:

From summer hikes to leaf peeping in the fall and skiing in the winter to spring picnics, there is no doubt that the Berkshires are a year-round destination.

I had the opportunity to enjoy a fall weekend in the Berkshires in October 2021. I loved how the Berkshires made for a great fall foliage getaway with its cozy inns and eateries along with its incredible hiking opportunities. Just like there are many great things to do in the Berkshires in the fall, I realized that Western Massachusetts is also a prime summer destination, especially if you visit Pittsfield!

Below is the best summer Berkshires itinerary for you to follow along during your weekend getaway to Pittsfield, Massachusetts:

Stroll Around Downtown Pittsfield:

The city of Pittsfield offers a lot from a farmers market to picturesque churches. During a summer weekend in the Berkshires, you must take time to fully explore the city!

One of the most romantic things to do in the Berkshires, if you’re traveling with a significant other, is to stroll Pittsfield’s streets, walk into art galleries like NUarts, admire the beautiful Church of St. Joseph, shop for souvenirs and home goods at Dory & Ginger (next to Hotel on North) and grab ice cream at King Kone.

An educational spot to visit during a family trip to the Berkshires is the Berkshire Museum. This fascinating museum combines arts, science and history to create an unforgettable experience. There is an aquarium, an exhibit that features local innovators and more!

Another one of the best things to do in the Berkshires this weekend is walk around the Pittsfield Farmers Market. Yes, this farmers market is a year-round event where you can shop for fresh and healthy local food, enjoy live music and chef demonstrations, plus more. There are also children’s activities and workshops!

Enjoy a Berkshire Camino Adventure:

One of the most memorable things to do in the Berkshires is a Berkshire Camino experience with Mindy. Inspired by the Camino de Santiago in Spain, which is what I did in summer 2019, Mindy leads curated and mindfully guided walks and hiking excursions in the mountains of Western Massachusetts.

The Berkshire Camino is a multi-day hiking journey that includes everything from the hike itself, which is always guided, to lodging, dining and transportation. You can choose between a 3-day, 4-night tour or a 4-day, 5-night experience with Berkshire Camino. Lodging is always at a local Berkshire inn or bed and breakfast and all food on the journey is farm-to-table!

During my summer weekend in the Berkshires, I enjoyed a single-day Berkshire Camino experience on the Green Trail at The Boulders and it was amazing! This property is owned and managed by Berkshire Natural Resources Council.

Prior to your hike, it’s recommended that you download the BNRC (Berkshire Natural Resources Council) Berkshires Trails App. It’s a comprehensive guide to hiking trails in the area, including state forests, parks and nonprofit land preserves.

On a Berkshire Camino journey, Mindy will lead your group with a “pilgrimage mindset” in order to de-stress while walking or hiking in nature. This adventure aims to positively impact the physical and mental health of individuals participating in the Berkshire Camino by allowing them to reconnect with themselves, their loved ones, nature and spirit.

When our group first started our guided walk, we set an intention. We also did an incredible mindset ritual that allowed us to leave our burdens behind.

After our hike, Mindy took us to a breathtaking overlook in Pittsfield State Forest that showcased the beautiful mountains of Western Massachusetts along with the nearby Catskills in New York State.

From there, we enjoyed a lovely summer picnic at the peaceful Berry Pond. Mindy catered our lunch from Marketplace Café in Downtown Pittsfield and it was perfect!

Overall, Pittsfield State Forest offers 35 miles of trails that are great for hiking, mountain biking as well as cross country and backcountry skiing in the winter. There are also campgrounds, swimming facilities and more.

(A cool fact about Pittsfield, Massachusetts is that the Appalachian Trail runs through the city, so you can hike parts of it! The Appalachian Trail is a 2,200-mile trail (3,500 kilometers) on the East Coast of the United States and it starts in Maine and goes to Georgia or vice versa. It also runs through parts of New Hampshire, Vermont, Massachusetts, Connecticut, New York, New Jersey, Pennsylvania, Maryland, West Virginia, Virginia, North Carolina and Tennessee.)

See a Performance at Barrington Stage:

If you’re wondering what to do in the Berkshires in the evening or on a rainy day, I recommend seeing a theater performance at Barrington Stage in Pittsfield.

Barrington Stage creates theater experiences that excite and entertain their audiences with dynamic and talented productions. During my summer weekend in the Berkshires, I saw Anna in the Tropics. It’s about Cuban immigrants who brought the cigar making industry to Ybor City in Tampa, Florida. At the factory, a lector tells the story of Anna Karenina, which leads the characters’ lives out of control.

Learn about the History of Cultural Pittsfield:

History in the Berkshires, MA goes back for centuries. The primary indigenous tribe of the Berkshires were the Mahicans and Algonquin speakers that resided along the Hudson and Housatonic Rivers.

The Berkshires were discovered by settlers in the 1700s and shortly after, it started to attract writers, novelists and artists from New York City. What is cool about Pittsfield is that it was where Herman Melville lived when he wrote Moby Dick. He first lived in New York City and moved to the Berkshires during summer 1850 at the age of 31.

You can visit Herman Melville’s home called Arrowhead in Pittsfield, Massachusetts and take a tour through the entire house. During the tour, you can learn in-depth about the life of Herman Melville and his family.

Another place to visit during a summer weekend getaway in the Berkshires is the Hancock Shaker Village. This small farm village in Pittsfield has been around since the late 1780s when around 100 Belivers consolidated a community on land that was donated by local farmers who had converted to the Shaker movement.

By the 1830s, the Shaker community population was the highest it had ever been at 300 people. One thing to note about the Shakers are that they believed in celibacy and because of that, they do not exist anymore.

This quaint village became a museum in 1960 and is now part of the National Historic Register. When you visit Hancock Shaker Village in Pittsfield, you can learn all about the in-depth history of the Shakers.

At Hancock Shaker Village, walk around the 1862 Round Stone Barn where you can say hi to farm animals like sheep, pigs, cattle, goats, donkeys, chickens and roosters. There is also a beautiful heirloom and medicinal herb garden to admire.

I also suggest making your way into the 1830 Brick Dwelling that housed the Shakers. You can view Shaker furniture, artifacts and art exhibits in this building. From the Brick Dwelling, also check out the Meetinghouse and Brick Poultry House at Hancock Shaker Village.

In addition, Hancock Shaker Village has a plethora of events that go on during the day. You can participate in traditional workshops, demonstrations, Shaker dances, tours, goat yoga and more.

Relax at a Pittsfield Lake:

A summer getaway is not complete without spending time on the water. Burbank Park at Onota Lake and Pontoosuc Lake Park are the best spots to make summer memories during a weekend in the Berkshires.

At Onota Lake, there is a beach, swimming area, fishing pier, public boat launch, walkways and a dog park to enjoy. You can also rent kayaks, a boat and bring tubes to the nearby Pontoosuc Lake Park.

Wine Taste at Balderdash Cellars:

One of the best things to do in the Berkshires in the summer is to visit a winery or brewery. Whether you visit the Berkshires in April or during the fall, you will not be disappointed by what this special area has to offer and all of the top things to do there!

Situated a little outside of Pittsfield, in the town of Richmond, MA, is Balderdash Cellars. It’s a fun spot to wine taste during a summer weekend in the Berkshires. At Balderdash Cellars, you can also do a wine production tour, listen to live music, admire beautiful mountain views, play yard games and socialize with friends.

Attend a Summer Ball Game:

If you’re a sports lover who enjoys a fun baseball game during the summer, then you must see the Pittsfield Suns play at Wahconah Park during your Berkshires weekend. The Pittsfield Suns are a summer baseball team that play in the Futures Collegiate Baseball League of New England.

Venture to Another Berkshire Village:

Even though there are numerous activities to enjoy in Pittsfield during a summer weekend in the Berkshires, I suggest visiting other villages in Western Massachusetts. Below is a list of places you should explore beyond Pittsfield:

• Hike the Peeskawso Peak Loop trail at Monument Mountain in Stockbridge.
• Enjoy everything that Great Barrington has to offer. There is a fun downtown area with cocktail bars, art galleries, boutiques and restaurants.
• Tour the Edith Wharton house in Lenox.
• Walk through the charming town of Lee.
• Visit the Massachusetts Museum of Contemporary Art in North Adams.
• Attend a summer concert at Tanglewood in Lenox.

If you visit the Berkshires in the winter, you must enjoy skiing or snowboarding at Jiminy Peak Mountain Resort in Hancock. Another one of the best things to do in the Berkshires in December is to see all the Christmas displays in Downtown Pittsfield and also enjoy the magical Hancock Holiday Nights at Hancock Shaker Village.

In addition to the Berkshires, here are other great places to visit in New England during summer:

Girl’s Trip on Martha’s Vineyard

Newport Summer Getaway

Long Weekend in Portland, Maine

Planning a memorable USA trip? Find more USA travel tips here.

I hope you all enjoyed discovering the best things to do during a summer weekend in the Berkshires of Massachusetts. If you have any questions, please email me at info@browneyedflowerchild.com.

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

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