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Things To Do in The Berkshires

From our centrally-located home base in Pittsfield, MA, you’re never more than 30-40 minutes away from any corner of The Berkshires. This gives you easy access to the region’s legendary cultural venues – museums, theater, music, and design – as well as outdoor adventures, antiquing, history, and of course, delicious culinary offerings from sun up to starry night.

Take time to explore the beautiful Berkshire scenery with these Scenic Driving Tours.

Our experienced Guest Services Team would be delighted to provide directions, suggestions, and tips on their favorite local haunts. Here are a few thoughts to get you started exploring…


Berkshire International Film Festival (BIFF)

A world-class festival held in venues throughout The Berkshires that showcases not only the latest in independent feature, documentary, short, and family films, but also hosts lively panel discussions and special events focusing on filmmakers and talented artists from both sides of the camera. Held each year in the spring. Visit for details.

Berkshire Theatre Group (Stockbridge, Pittsfield)

Created when two of Berkshire County’s oldest cultural institutions came together in 2010, the BTG oversees the development, production, and presentation of theatre, music, and the performing arts on multiple stages in both Stockbridge and Pittsfield. Visit for a complete calendar for all their venues.

The Clark Art Institute (Williamstown)

Originally chartered in 1950 to house the extensive art collection of Sterling and Francine Clark, the Institute opened to the public in 1955 and has expanded its collection to become one of the most respected art museums in the world. Known for its intimate galleries and stunning natural environment, it’s also one of the few US institutions that combines a public art museum with research and academic programs, including a major art history library. Visit for more information.

Hancock Shaker Village (Pittsfield)

Home to the Shakers for more than 220 years, Hancock Shaker Village is now an outdoor history museum dedicated to preserving the Shaker legacy and making that story relevant and illuminating for today’s visitors. Situated on 750 acres of picturesque farm, field, and woodland in the bucolic Berkshires of Massachusetts, the Village consists of 20 historic buildings, a working farm and heirloom gardens, and a premier collection of 22,000 authentic Shaker artifacts. Visit for more information.

Jacob’s Pillow Dance (Becket)

A National Historic Landmark and National Medal of Arts recipient, Jacob’s Pillow is home to America’s longest running dance festival each summer and one of its most prestigious dance training centers. Each season, more than 50 dance companies delight audiences with 200 performances, talks, and events, and community programs are designed to educate and engage dance enthusiasts of all ages. Visit for more information.

The Massachusetts Museum of Contemporary Art (North Adams)

MASS MoCA is one of the world’s premier centers for spotlighting some of the freshest, surprising, and most challenging art of our time. Broad, soaring galleries with 110,000 square feet of open, flexible space inspire and empower artists both well-known and emerging to create large-scale and complex installations that are impossible to realize in conventional museums. More than 80 major new works of art and more than 50 performances have been created through fabrication and rehearsal residences here. Details on the latest exhibitions can be found at

Shakespeare & Company (Lenox)

One of the largest Shakespeare Festivals in the country, this legendary festival develops and performs Shakespeare classics and contemporary new plays of social and political significance. The Company embraces the core values of Shakespeare’s work: collaboration, commitment to language, visceral experience, and classical ideals…expressed with physical prowess and an embodied contemporary voice. Visit for a full season calendar.

Tanglewood (Lenox)

One of the most legendary music festivals in the world, Tanglewood – the summer home of the Boston Symphony Orchestra since 1937 – attracts more than 300,000 visitors each season. Orchestra concerts by the BSO and the Boston Pops are featured on a robust performance calendar that also includes visiting ensembles, recital and chamber music concerts, and some of today’s leading popular artists. Visit for a full season calendar.

Hotel on North is proud to be a Preferred Hospitality Partner of the new Tanglewood Learning Institute opening this summer.   Programs include immersion weekends, interactive talks, open rehearsals, films, master classes, unconventional performances, and visual arts experiences.

Williamstown Theatre Festival (Williamstown)

A Tony Award-winning theatre company that brings America’s finest actors, directors, designers, and playwrights to the Berkshires each summer. From classic plays with innovative productions to bold new plays and musicals, WTF presents a diverse array of performances with each season, and offers rich cultural events to complement them, such as Free Theatre, Late-Night Cabaret, readings, workshops, and educational programs. Check out what’s on tap this season at


Main Street Dining

Hotel on North is part of the Berkshire-based Main Street Hospitality Group, which means you’ll be treated like family in several other dining venues in the region. Our Guest Services Team can give you directions, so if you’re here long enough to explore other places, we suggest you check these out:

The Red Lion Inn

Stockbridge – 20 minutes south on Route 7 – 30 Main Street, Stockbridge, 413-298-5545,

The legendary Main Dining Room at the Red Lion Inn

Soft candlelight, crystal chandeliers, antique china, and colonial pewter underscore the historic atmosphere at this quintessential New England inn restaurant. Traditional regional favorites and some fresh, local surprises are complemented by a wine list of more than 400 selections. Open daily for breakfast, lunch, and dinner.

 The Widow Bingham’s Tavern

A cozy spot that’s steeped in history, you’ll feel like you’ve stepped back into Colonial America while dining here. Hearty sandwiches, fresh salads, traditional entrees, savory soups…all served in view of a fully stocked bar that cheerfully pours out pints of local craft beers, wines, and spirits. Be sure to check out the memorabilia that adorns the walls and ceiling. Betcha you spot your childhood lunchbox somewhere. Open daily for lunch and dinner.

The Lion’s Den Pub

Tucked away in the cellar, this local hot spot offers live entertainment seven nights a week, and never a cover charge. Classic pub fare, with an extensive beverage menu from the bar…and in the cooler months, you’ll want to grab a table next to the roaring fire. Check out the music calendar online at to see who’s appearing while you’re in town. Open Mon-Thurs from 4-10pm, Friday from 4-11pm, and Sat/Sun from noon to 11pm.

The Courtyard (Seasonal)

Who doesn’t want to sit outside from June – September? Enjoy our flower-filled, umbrella-graced patio garden…for lunch, dinner, or evening cocktails under the starry sky. There’s a cookout every Friday too. Lunch is served from 12-4pm daily. Dinner starts at 5:30pm.

Seeds Market Café at Hancock Shaker Village

1843 W Housatonic St, Pittsfield, 413-443-0188, 

Seeds Market Cafe highlights the spirit and nature of the Shaker’s authentic living heritage.  Located steps from heirloom vegetable and herb gardens, the fresh-picked menu items celebrate Shaker-inspired, neighborhood-sourced food, as well as special event dinners and catering for all occasions.  Open seasonally.


Other Delicious Options

Other fabulous restaurants we recommend in The Berkshires include…


420 Stockbridge Rd, Suite 3
Great Barrington, MA 01230

“Serious about food, drink and your dining experience.”

Chez Nous

150 Main Street
Lee, MA 01238

“Charming bistro pairs French country classics with a big wine list in a cozy, romantic setting.”

John Andrews, A Farmhouse Restaurant

224 Hillsdale Road
Great Barrington, MA 01230

“Specializes in regional American cuisine with an emphasis on local fresh and seasonal ingredients and Italian regional influences.”

 Mezze Bistro + Bar

777 Cold Spring Road (Route 7)
Williamstown, MA ‎01267

“Contemporary American cuisine highlighting the best of the season in support of independent farmers and artisan producers.”

Nudel – seasonally inspired food

37 Church Street
Lenox, MA 01240

“A creative American pasta bar which takes its inspiration from the bounty provided by the local farms and producers of Berkshire County.”


3 Center Street
West Stockbridge, MA 01266

“Popular bistro bringing together classic French dishes, a global tapas menu & a bustling bar scene.”

Xicohténcatl Mexican Restaurant

50 Stockbridge Road
Great Barrington, MA 01230

“Colorful eatery known for its mole & margaritas, with patio seating & live music on weekends.”



Specialty Foods

Visit the many specialty food stores The Berkshires has to offer for all of your picnic needs!

Berkshire Organics

813 Dalton Division Road
Dalton, MA 01226

“Berkshire Organics is a family-owned business created to bring area residents and local farms together.  Our market offers the freshest, local and organic, non-GMO produce, meat, and groceries.”

Guido’s Fresh Marketplace

1020 South Street
Pittsfield, MA 01201

Guido’s Fresh Marketplace has been the premier purveyor of quality produce in Berkshire County, MA. The finest vegetables, organic, farm to table, and natural foods.

Nejaime’s Wine Cellar

60 Main Steet Street
Lenox, MA 01262

3 Elm Street
Stockbridge, MA 01262

“Featuring the Berkshires’ premier selection of wine, liquor, beer, cheese & specialty foods. Conveniently located in Lenox Village & Stockbridge, we offer a wide variety of gourmet foods, cheese, picnics, & all the wine, beer, and liquor you want in downtown Lenox & Stockbridge!”

Spirited Wines

Jim Nejaime – Wine Merchant

444 Pittsfield Road
Lenox, MA 01240

“Voted Berkshire’s best fine wine and beverage marketplace. We take great pride in our extensive selection of wines and travel around the world to bring you great values, rare gems, and the finest quality to satisfy your palate. To complement your shopping experience, we offer artisanal cheeses, charcuterie, specialty foods, discount liquors, craft beers, gift baskets, picnics and much more”



For more things to see and do in the region, visit, the delightful and informative website of our friends at the Berkshire Visitors Bureau.