110+ Things to Do in the Berkshires


The Berkshires, a Truly Special Place

The Berkshires is a rural region located in western Massachusetts. Many restaurants, hotels, and shops in the Berkshires were first founded in the late 1700s and early 1800s. The region then boomed during the Gilded Age shortly after the Civil War. Known for its incredible hikes, fall-foliage viewing opportunities, a strong farm-to-table food scene, and a plethora of art galleries, theaters, mansions, and concerts, you’ll quickly see why the Berkshires live up to their hype.

My parents have a lake house in Stockbridge and over the years I’ve come to love the Berkshires. After spending a few days here, you’ll quickly understand why it’s such a special place. While the Berkshires cover a large swath of western Massachusetts, our favorite towns within the Berkshires are Lenox, Stockbridge, West Stockbridge, Great Barrington, and Pittsfield. There is so much to eat, drink, see and do, and the people are very kind. I feel very fortunate to have a family home in the Berkshires.


1. Lenox

Founded in 1767, and with a current population of around 5,000, Lenox has a lot to offer while maintaining its historic, small-town charm. From museums and parks to theaters, bookstores, coffee shops, and wine bars, Lenox really comes alive in the summer months. It’s a charming town dotted with massive privately-owned mansions, historic libraries, and a lot of natural beauty.  You’ll find something for everyone here.


Top Restaurants and Bars in Lenox:

  • Bistro Zinc, for French fare in a chic dining room
  • Brava, a wine bar offering pizza, charcuterie boards, and tapas
  • Firefly, a gastropub offering hardy American eats
  • Haven, for egg sandwiches and coffee
  • Lenox Coffee, for coffee, tea, and donuts
  • Olde Heritage Tavern, for American pub food with TVs and a patio
  • Pizza Boema, for wood-fired pizza, wine, and cocktails
  • Prime, for high-quality Italian cuisine
  • The Scoop, for ice cream, candy, and brownies

Top Shops in Lenox:

  • The Bookstore, for an independently owned bookstore with a wine bar inside, called Get Lit
  • Casablanca, a luxury boutique for men and women
  • Ceri, for innovative, boutique items for women
  • Colorful Stitches, for knitters and crocheters
  • Janet Pumphrey Gallery, for handmade art
  • MacKimmie Co., a home and lifestyle shop
  • Nejaime’s, a wine cellar with wine, beer, spirits, bread, cheese, dried fruits, and chocolate
  • Olivia!, for gourmet olive oils and vinegar
  • The Wit Gallery, a contemporary gallery with photography, glass, and paintings
  • The World’s Best Chocolate and Art, for sweet treats, paintings, and jewelry

2. Stockbridge

Stockbridge, a picturesque village in the Berkshires emanates New England charm. In 1953, Stockbridge’s most famous resident, artist Norman Rockwell, moved to Stockbridge where he remained until his death in 1978. Stockbridge has an incredible amount of cultural attractions including music festivals, theaters, major art museums, galleries, and historic homes and gardens. Stockbridge is said to be one of the most quintessential small towns in America.


Top Restaurants and Bars in Stockbridge:

  • Elm Street Market, for fresh fruits, veggies, deli meats, and cheese
  • The Lost Lamb, for breakfast sandwiches and fine pastries 
  • Main Street Cafe, a charming spot dishing up traditional American eats and baked goods
  • Michaels, for classic, comforting bar food
  • Once Upon A Time, an intimate bistro featuring locally sourced dishes
  • Peace, Love, and Chocolate, for chocolatey treats and ice cream
  • The Red Lion Inn, for elegant, New-England inspired dining
  • Stockbridge Coffee & Tea, for coffee, lattes, and baked goods
  • Tiffany’s Cafe, for locally sourced breakfast, lunch, and dinner options

Top Shops in Stockbridge:

  • Heirlooms Jewelry, for diamonds, opals, ambers, and unique estate pieces
  • John R. Sanderson Rare Books, for unique literature
  • Nejaime’s, a wine cellar with wine, beer, spirits, bread, cheese, dried fruits, and chocolate
  • Seven Arts Gift Shop, for a great selection of vinyl records and CDs
  • Sidetracks, for accessories, clothing, and baby items
  • Stockbridge General Store, for ice cream, sandwiches, soups, and desserts
  • Williams & Sons Country Shop, since the 1790s, they’ve been offering jams, jellies, toys, games, postcards, and more

3. West Stockbridge

This tiny town wraps around the Williams River and offers small-town charm. In the heart of West Stockbridge, you’ll find an old grist mill that first began operating in 1818. In 1900, the Williams River was used to power the mill and provide electricity to West Stockbridge. As you walk around this quaint town you’ll find an art gallery, antique shop, book store, and a great coffee shop, along with a few restaurants.


Top Restaurants and Bars in West Stockbridge

  • No. Six Depot Roastery & Cafe, for coffee, smoothies, and wraps
  • Public Market, for fresh produce, wine, beer, and groceries
  • Rouge Restaurant and Bistro, for fancy American cuisine
  • The Tap House at Shaker Mill, for steak, seafood, quinoa cakes, and everything in between
  • Truc Orient Express, for authentic Vietnamese food

Top Shops in West Stockbridge

  • Cassandra Events, for special event floral arrangements
  • Charles H. Baldwin & Sons, a general store selling candy, puzzles, jams, and spices since 1888 
  • Flourish Market, for repurposed and refreshed vintage furniture, lighting, jewelry, and trinkets
  • Hotchkiss Mobiles Gallery and Studio, for hand-crafted, high-quality mobiles
  • R&R West Stockbridge, for home goods and furniture
  • Shaker Mill Books, for new and used books

4. Great Barrington

In 2012, the Smithsonian Magazine listed Great Barrington as the number one Best Small Town in America describing it as, “Big-city smart meets New England natural in an art-rich mountain setting.” Great Barrington is most known for being the birthplace of author and civil rights activist W.E.B. Du Bois, and for having a plethora of restaurants with quality cuisine, and tons of antique shops, which give the town so much personality.


Top Restaurants and Bars in Great Barrington

  • 20 Railroad Public House, for great burgers and fries
  • Aegean Breeze, for Mediterranean and Greek food
  • Baba Louie’s, for excellent pizza
  • Barrington Brewery and Restaurant, for American bar food
  • Berkshire Food Co-op, for fresh produce and a deli
  • Cafe Adam, for fancy American food, like clams, steak, and calamari
  • Great Barrington Bagel, for excellent bagels that pass the test of my New York family
  • Koi, for excellent Chinese and Thai cuisine
  • Naji’s, for Lebanese and Mediterranean food
  • Number Ten, for a steakhouse
  • SIAM Square, for Thai food
  • Xicohtencatl, for Mexican food

Top Shops in Great Barrington

  • Barrington Outfitters, for women’s clothing and shoes
  • Boho Exchange, for thrift shop finds in a bright yellow house
  • The Emporium, a consignment shop with antiques and vintage items
  • GB9, for women’s clothing and accessories
  • Griffin, for home decor, and men’s and women’s clothing
  • The Little Store, for antiques
  • Matrushka Toys & Gifts, for children’s toys
  • One Mercantile, for home decor and gifts
  • Robin’s Candy Shop, for an incredible selection of sweet treats
  • TP Saddle Blanket, for clothing and accessories with a cowgirl theme

5. Pittsfield

Pittsfield is known as the heart of the Berkshires and is the largest of all the towns in this area with a population of 47,000. Pittsfield has been featured on best places to retire lists and was even called the “Brooklyn of the Berkshires.” Being the cultural center of the Berkshires you’ll find a ton of festivals, places to shop, food and drink experiences, museums, sporting events, and more! You’ll also find shopping malls and big chain stores, like Target, Marshalls, Wal-Mart, and Stop & Shop.


Top Restaurants and Bars in Pittsfield

  • Berkshire Mountain Bakery, for incredible fresh-baked bread and sweet treats
  • District Kitchen & Bar, for fancy American bar food, like mac and cheese, mussels, and Steak Frites
  • Electra’s Cafe, for delicious salads and fresh fruit
  • Koto Hibachi Steak House, for hibachi and sushi
  • La Fogata, for Latin and Colombian cuisine
  • Mazzeo’s Ristorante, for Italian food
  • Mission Restaurant, for Spanish food with a wine bar
  • Patrick’s Pub, for American and Irish cuisine
  • The Roasted Garlic, for burgers and wings 
  • Tito’s Mexican Grill, for Mexican and Mediterranean food
  • Vong’s Thai Restaurant, for excellent Pad Thai
  • Wandering Star Craft Brewery, for a unique selection of beers where they grow their own hops

Top Shops in Pittsfield

  • Circa, a furniture store
  • Designer Consigner, a consignment shop with clothing and accessories
  • Dory and Ginger, for high-quality home goods
  • The Garden, for hats, shoes, bikes, snowboards, and backpacks
  • Kissy’s, a women’s clothing store
  • New Moon Gifts, a gift shop

Best Things to Do in the Berkshires:

  • Berkshire Botanical Garden, for 15 acres with more than 3,000 plants.
  • Berkshire Museum, a museum filled with fine art, natural sciences, and ancient artifacts.
  • The Clark Art Institute, for an art museum and research institution.
  • Hancock Shaker Village, a living history museum that brings the Shaker story to life and preserves it for future generations.
  • Herman Melville’s Arrowheadthe home to author Herman Melville, who wrote Moby Dick.
  • Jacob’s Pillow, a dance center, school, and performance space known for summer dance festivals. The facility also includes a professional school and extensive archives as well as year-round community programs.
  • Kripalu Center for Yoga and Health, for a variety of packages, from a one-time massage to an entire week of meals, yoga classes, educational seminars, and paddleboarding lessons.
  • MASS MoCa, the Massachusetts Museum of Contemporary Art is one of the largest centers for contemporary visual art and performing arts in the United States.
  • The Mount, Edith Wharton’s Estate, is a National History Landmark. They offer tours of the home and live concerts on the wrap-around deck, which overlooks expansive manicured gardens.
  • Naumkeag, for a stunning public garden, historic home, and 48-acre architectural masterpiece.
  • Norman Rockwell Museum, home to the world’s largest collection of original Norman Rockwell paintings.
  • Stockbridge Cemetary, take a quiet walk and see if you can find Norman Rockwell’s gravestone.
  • Tanglewood, summer home to the Boston Symphony Orchestra, as well as theater and concerts. Be sure to get there early if you want a good spot on the lawn.
  • Ventfort Hall, home to Sarah Morgan, JP Morgan’s sister, is a historic, Jacobean-style mansion and museum.

Top Hikes in the Berkshires:

There are tons of hikes all of varying difficulty and length in the Berkshires. Whatever you’re looking for, you can find it. Click here for an extensive list of some of the best hikes in Massachusetts.

  • Appalachian Trail, this famous trail runs from Atlanta to Maine and passes through the Berkshires. Some of the more popular sections are Upper Goose Pond Trail, Lee to Tyringham Trail, and Finery Pond Trail.
  • Bash Bish Falls, an 80-foot waterfall on the Massachusetts and New York border.
  • Burbank Trail, a 3.2-mile loop with an overlook point.
  • Housatonic Riverwalk, This stretch of the Appalachian Trail runs between Kent and Cornwall Bridge. It totals about 5 miles one-way.
  • Laura’s Tower, a heavily wooded and quiet walk. It doesn’t take too long to get to the top and once you do, there is a staircase and platform that allows you to get a little higher and get an even better view of the surrounding towns.
  • Monument Mountain, this hike is very steep. It’s an intense workout on your way up, but once you get to the top, the vistas are incredible, and the walk back down is quick! This hike is also said to be the inspiration for Herman Melville’s Moby Dick.
  • Mount Greylock, a popular hiking spot and the highest point in Massachusetts, also part of the Appalachian Trail.
  • Olivia’s Overlook, an overlook where you can see the Stockbridge Bowl and surrounding mountains.
  • Parsons Marsh Reserveis part of the Undermountain Valley, a wetland and forest area in the heart of Lenox.
  • Pittsfield State Forest, 30 miles of trails for hiking, mountain biking, horseback riding, and more.
  • Race Brook Falls, for a hike to a beautiful waterfall that has three tiers.

Sailing the Stockbridge Bowl

A Trip You Won’t Forget

The Berkshires are a special place with an incredible amount of history and culture, dating back to the 1700s. Every time I go I stumble upon another gem. I’m so fortunate that my parents have a lake house in Berkshires and after ten years, I still want more. There is always a new hike to explore, another restaurant to check out and so many galleries, museums, and concerts.

Looking for more inspiration? Check out my posts on Waseca, Stillwater, and Pine City!


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