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To Do & See

Hoosac Valley Train Ride

3 Hoosac St, Adams, Massachusetts 01220

Mentions

Bringing fun and scenic train rides back to the Berkshire Mountains of Massachusetts, connecting North Adams and Adams!

Adams, Family Fun, Indoor Activity, Kid Friendly Activity, Museums, North Adams & Williamstown

Naumkeag

5 Prospect Hill Rd, Stockbridge, Massachusetts 01262

Mentions

With its gracious house, magnificent gardens, and panoramic views, Naumkeag is a quintessential country estate of the Gilded Age

Arts & Culture, Gardens, Guided Tours/Excursions, Hiking, Historic Sites, Stockbridge, Venues, Weddings

Clark Art Institute

225 South St., Williamstown, Massachusetts 01267

Mentions Events

The Clark Art Institute showcases a robust collection of art spanning from the Renaissance to the early twentieth century.

Arts & Culture, Dance, Galleries, Kid Friendly Activity, Museums, Music, North Adams & Williamstown

Eastover Estate & Eco Village

430 West Street, Lenox, Massachusetts 01240

Events

Eastover is a 600 acre holistic retreat center only minutes away from the center of downtown Lenox, ideal for teachers, groups, organizations and companies to host retreats, workshops, and group events. It offers spacious studio facilities including

Health & Wellness, Lenox, Wellness Retreat

Tanglewood Linde Center

3A W Hawthorne Rd, Lenox, Massachusetts 02140

The Boston Symphony’s Tanglewood Learning Institute (TLI) presents more than 40 performances and multidisciplinary events that engage curious minds.

Arts & Culture, Educational, Lenox, Live Music, Music

The Big E

1305 Memorial Ave, West Springfield, Massachusetts 01089

The Big E, also known as The Eastern States Exposition, is billed as "New England's Great State fair". It is the largest agricultural event on the eastern seaboard and the seventh-largest fair in the nation.

Arts & Culture, Fall Festivals, Family Fun, Kid Friendly Activity, Music, To do and See

Lenox Apple Squeeze

Main Street, Lenox, Massachusetts

Mentions

One of the newer and much celebrated annual traditions with a lot of popularity celebrating the apple harvest with a lot of food and artisan vendors in addition to great live music.

Arts & Culture, Fall, Fall Festivals, Festivals, Kid Friendly Activity, Lenox

Tanglewood

297 West St., Lenox, Massachusetts 01240

Mentions Events

Tanglewood, on a vast, green property in the Berkshires region of Massachusetts, is the summer home of the Boston Symphony Orchestra and the Boston Pops and from spring through fall, Tanglewood hosts a large variety of live music performances.

Arts & Culture, Family Fun, Historic Sites, Lenox, Music

Lauren Clark Fine Art

684 Main Street, Great Barrington, Massachusetts 01230

Mentions

The gallery represents over 40 local and internationally recognized artists working as painters, printmakers, potters, glass blowers and jewelers.

Arts & Culture, Galleries, Great Barrington

Mount Greylock Visitors Center

30 Rockwell Road, Lanesborough, Massachusetts 01237

The Visitor Center is open year-round. Features include park trail maps, orientation, regional tourist information and exhibits on natural and cultural stories of the park. There is a large bronze model of the mountain range and the hiking paths, a n

Hiking, Lanesborough, mountain, Mountain Biking, Outdoor Adventure, To do and See

The Mount, Edith Wharton's Home

2 Plunkett St, Lenox, Massachusetts 01240

Mentions Events

The Mount is a National Historic Landmark and cultural center that celebrates the intellectual, artistic, and humanitarian legacy of Edith Wharton.

Arts & Culture, Gardens, Guided Tours/Excursions, Historic Sites, Lenox, Venues, Weddings

3rd Thursday 2019- Downtown Pittsfield

This free, family- friendly, cultural street festival offering live music and performances, local food and craft vendors, street performers, and more, runs every third Thursday from May-October.

Arts & Culture, Fall Festivals, Festivals, Kid Friendly Activity, Pittsfield, Summer Festivals

The Triplex Cinema

70 Railroad St, Great Barrington, Massachusetts 01230

The Triplex Cinema in the heart of Great Barrington is a 4-screen movie house featuring independent films & first-run Hollywood hits, plus community events.

Cinema, Family Fun, Great Barrington, Kid Friendly Activity

2019 Berkshire International Film Festival

70 Railroad Street, Great Barrington, Massachusetts

Mentions

BIFF 2019 May 30th - June 2nd. A much-celebrated film festival introducing the best of independent, feature, documentary & short films. Panel discussions, special events & more.

Arts & Culture, Festivals, Great Barrington, Summer Festivals

Berkshire Botanical Garden

5 W Stockbridge Rd, Stockbridge, Massachusetts 01262

Mentions Events

The display gardens are both functional and ornamental and are among the oldest in the region.

Arts & Culture, Gardens, Guided Tours/Excursions, Kid Friendly Activity, Stockbridge

Freshgrass Festival

1040 Mass MoCA way, North Adams, Massachusetts 01247

Mentions

September 20-22, 2019- Surrounded by the beautiful backdrop of the Berkshire mountains in northwestern Massachusetts, the two day festival takes place at Mass MoCA, promoting innovative grassroots music.

Arts & Culture, Fall Festivals, Festivals, North Adams & Williamstown

Balderdash Cellars

81 State Road, Richmond, Massachusetts 01254

Mentions Events

They focus on producing ultra-premium (wicked to New England folks) wines from grapes grown by world-class California vineyards.

Artisanal Shop, Casual, Family Fun, Live Music, Restaurants, Winery

Solid Sound Festival 2019 at Mass MoCA

1040 MASS MoCA Way, City of North Adams, Massachusetts 01247

Wilo's Music & Arts Festival June 28th - 30th, 2019. at Mass MoCA, North Adams MA

Arts & Culture, Festivals, Live Music, Music, Spring Festivals, Summer, Summer Festivals

First Fridays Artswalk

North Street, City of Pittsfield, Massachusetts

Mentions

First Fridays Artswalk kicks off a month of art February through December displayed indoors in galleries, retail & hospitality businesses along the North St.

Arts & Culture, Fall Festivals, Festivals, Pittsfield, Summer Festivals, Winter Festivals

Stockbridge Summer Arts & Crafts Festival-2019

Main Street, Stockbridge, Massachusetts

August 17 & 18, 2019- Jury-selected artists and crafters in various mediums: oil and watercolor paintings, ceramics, fiber arts, glass blowing, and others. Free admission. Rain or Shine.

Arts & Culture, Festivals, Kid Friendly Activity, Stockbridge, Summer, Summer Festivals

6th Annual Lenox Rhubarb Festival 2019

Main Street, Lenox, Massachusetts 01240

The Lenox Rhubarb Festival is a annual celebration of rhubarb in the Historic Village of Lenox, MA.

Arts & Culture, Festivals, Lenox, Summer Festivals

Berkshire Jewish Film Festival 2019

197 East Street, Lenox, Massachusetts 01240

Beginning July 8th 3019- 33rd season of American & International Jewish Film.

Arts & Culture, Festivals, Lenox, Summer Festivals

Berkshire Opera Festival 2019

14 Castle St, Great Barrington, Massachusetts

Berkshire Opera Festival presents "Don Pasquale" at The Mahaiwe Theatre, August 24th, 27th & 30th. The crusty old bachelor Don Pasquale decides to marry a much younger wife and produce an heir to spite his nephew, Ernesto,

Arts & Culture, Festivals, Great Barrington, Summer Festivals

Aston Magna Music Festival - 2019

352 Main Street, Great Barrington, Massachusetts 01230

Early Music Festivals' 46th season! JS Bach, Mozart & more, performed on period instruments in an intimate setting. Thursdays, Fridays & Saturdays, June 27th- August 10th, 2019.

Arts & Culture, Festivals, Great Barrington, Music, Summer Festivals

Berkshires Arts Festival 2019

380 State Rd, Great Barrington, Massachusetts

Mentions

July 5th-7th, 2019- A very large and popular juried art event. 195 artisans, live music, demonstrations, inside, tents, lodge,free parking.

Arts & Culture, Festivals, Galleries, Great Barrington, Kid Friendly Activity, Summer Festivals

Yankee Candle Village

25 Greenfield Road, South Deerfield, Massachusetts 01373

One of New England’s most popular destinations, Yankee Candle Village offers a unique shopping, entertainment and dining experience.

Artisanal Shop, Deerfield, Family Fun, Indoor Activity, Kid Friendly Activity

Cascade Waterfall

180 Marion Ave, Lenox, Massachusetts 01247

Mentions

Cascade Trail Park in North Adams

Family Fun, Hiking, North Adams & Williamstown, Outdoor Adventure

Berkshire Running Center

34 Depot St., Pittsfield, Massachusetts 01201

Mentions

Family owned run-specialty store and training center. 50 yrs of Run- training,coaching and performance based programs. Certified Personal Trainers, Coaches and Cycling Instructors. Top of the line 16 bike Keiser indoor cycling studio. MINDBODY app

Outdoor Adventure, Pittsfield, Shop

Berkshire Botanical Garden Harvest Festival

5 West Stockbridge Road, Stockbridge, Massachusetts

Mentions

October 6th and 7th- A festival highlighting all things autumnal at the Berkshire Botanical Garden's Harvest Festival. Over 100 craft & food vendors plus family & farm activities.

Arts & Culture, Fall Festivals, Festivals, Gardens, Kid Friendly Activity, Stockbridge

The Cobbles

41 Railroad St, Cheshire, Massachusetts 01225

Mentions

Cheshire Cobbles via Appalachian Trail is a 2 mile moderately trafficked out and back trail located near Cheshire that features beautiful wild flowers. The trail is rated as moderate offers a number of activity options.

Hiking, Outdoor Adventure

Norman Rockwell Museum

9 MA-183, Stockbridge, Massachusetts 01262

Mentions Events

Significant collection of the artist's original work & memorabilia on display in his hometown.

Arts & Culture, Galleries, Historic Sites, Kid Friendly Activity, Museums, Stockbridge

MASS MoCA

87 Marshall St., North Adams, Massachusetts 01247

Mentions Events

MASS MoCA is one of the world’s liveliest centers for making and enjoying today’s most evocative art.

Arts & Culture, Dance, Museums, Music, North Adams & Williamstown

Berkshire Theater Group- The Colonial Theatre

111 South Street, Pittsfield, Massachusetts 01201

Mentions Events

The fully restored stage boasts pristine acoustics, classic gilded age architecture and state of the art technical systems and hosts family entertainment, comedy, live music and more year round.

Arts & Culture, Dance, Music, Pittsfield, Theatre

Berkshire Theatre Group- Unicorn Theatre

6 East St., Stockbridge, Massachusetts 01262

Mentions

The Unicorn Theater, Stockbridge MA, a theatrical jewel, is the home for new and emerging artists, and challenging and thoughtful work.

Arts & Culture, Stockbridge, Theatre

Ubu Theater

Town of Tyringham, Massachusetts

A Theater in Tyringham, MA whose mission is to provide artistic experiences that empower and engage communities.

Arts & Culture, Summer Festivals, Theatre, Tyringham

Cove Lanes

109 Stockbridge Road, Berkshire, Massachusetts 01230

Enjoy bowling under the disco lights with music and 4 projection screens playing music videos. Fun for all ages!

Bowling, Great Barrington, Indoor Activity, Kid Friendly Activity

Frelinghuysen Morris House & Studio

92 Hawthorne Street, Lenox, Massachusetts 01240

Mentions

Visit the home of American Abstract Artists George L.K. Morris and Suzy Frelinghuysen, set on a 46-acre estate in the heart of Lenox, Massachusetts.

Arts & Culture, Galleries, Historic Sites, Lenox, Museums

Ventfort Hall Mansion and Gilded Age Museum

104 Walker St, Lenox, Massachusetts 01240

Mentions Events

Located on spacious grounds in the heart of the village, Ventfort Hall is an imposing Jacobean Revival-style mansion built in 1893, while The Museum of the Gilded Age interprets the great changes that occurred in American life, industry and society.

Arts & Culture, Historic Sites, Lenox, Museums

Berkshire Museum

39 South St, Pittsfield, Massachusetts 01201

Mentions Events

Their mission is bringing people together for experiences that spark creativity and innovative thinking by making inspiring educational connections among art, history, and natural science

Arts & Culture, Indoor Activity, Kid Friendly Activity, Museums, Pittsfield

Country Club of Pittsfield

639 South St., Pittsfield, Massachusetts 01201

Mentions

The Country Club of Pittsfield provides its members a beautiful, golf, racquet and water-sport experience. The club is open year-round for member dining, activities and for hosting weddings/events of all sizes.

Golf, Outdoor Adventure, Pittsfield, Sporting Goods, Venues, Wedding Planners, Weddings

Gallery W @the Whit

42 Wendell Ave, Pittsfield, Massachusetts 01201

The Whitney Center for the Arts is in downtown Pittsfield, MA, Referred to as “The Brooklyn of the Berkshires”.

Arts & Culture, Galleries, Pittsfield

Canyon Ranch

165 Kemble St, Lenox, Massachusetts 01240

Mentions Events

A Canyon Ranch experience is an immersive exploration of mind-body wellness in a relaxed setting of casual elegance and unsurpassed personal service – where every moment is yours to savor.

Breakfast Included, Fireplace, Fitness, Free WiFi, Health & Wellness, Honeymoon, Hotel, Jacuzzi, Lenox, Luxury & Resorts, Non-Smoking Hotel, Pool, Spa, Wellness Retreat

Regal Cinemas at Berkshire Mall

123 Old State Rd, Lanesborough, Massachusetts 01237

Theater complex with multiple screens featuring new release films, concession stand and large, reclining, plush seating.

Cinema, Indoor Activity, Kid Friendly Activity, Lanesborough

Jiminy Peak

37 Corey Rd, Hancock, Massachusetts 01237

Mentions

Jiminy Peak Mountain Resort is the largest ski and snowboard resort in southern New England, summer home to Mountain Adventure Park and the only mountain resort in North America to generate its own energy using alternative wind power.

Adventure Parks, Downhill Skiing & Boarding, Family Fun, Hancock, Kid Friendly Activity, Outdoor Adventure, Ski & Snowboard Rentals, Skiing & Boarding, Sledding & Tubing, To do and See, Venues, Weddings

Lichtenstein Center for the Arts

28 Renne Ave, Pittsfield, Massachusetts 01201

Mentions Events

The Lichtenstein Center for the Arts is Pittsfield's city owned community arts center, featuring nine working artist studios, a ceramics studio, community room, and art gallery featuring changing exhibitions, classes, performances and more!

Arts & Culture, Galleries, Pittsfield

Jacob's Pillow Dance

358 George Carter Rd, Becket, Massachusetts 01223

Mentions

Jacob's Pillow is a treasured 220-acre National Historic Landmark, a recipient of the prestigious National Medal of Arts, and home to America’s longest-running international dance festival.

Arts & Culture, Becket, Dance, Theatre, To do and See

The Mahaiwe Performing Arts Center

14 Castle St., Great Barrington, Massachusetts 01230

Mentions Events

The Mahaiwe Performing Arts Center has steadily presented a thoughtful selection of music, dance, theatre, opera, talks, and movie classics since the early 1900's.

Arts & Culture, Dance, Family Fun, Great Barrington, Music, Theatre

The Berkshire Concert Choir

Berkshire, Massachusetts

The Berkshire Concert Choir continues to grow in popularity having performed several times at Tanglewood, on Northeast Public Radio and local community television, and on several European tours.

Arts & Culture, Music, Pittsfield

The Infield

10 Lyman Street, Pittsfield, Massachusetts 01201

The Infield is the first and sole multi-sport indoor training facility in the Berkshire County area.

Family Fun, Fitness, Indoor Activity, Kid Friendly Activity, Pittsfield, Sports

The Southfield Store

163 Norfolk Road, Southfield, Massachusetts 01259

Transformed from a classic New England general store into a Cafe and Coffee Bar, with seating for 30 people and daily food service. Serving breakfast, lunch, & dinner.

American, Artisanal Shop, Arts & Culture, Bakery, Breakfast, Brunch, Casual, Catering, Coffee Shop/Cafe, Dessert, Dinner, Family Friendly Dining, Farm To Table, Historic Sites, Lunch, Mexican, Outdoor Seating, Quick Bites, Restaurants, Venues

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