297 W. Street, Lenox MA 01240
Summertime home of the Boston Symphony and full time home to their learning institute, Tanglewood’s festival is one of the iconic annual events that draws the masses every July. The campus is yours to explore with tours and prelude concerts occurring throughout the year for you to enjoy.
2 Harris St, West Stockbridge, MA 01266
The Foundry began as a glass blowing studio in 1994 and has since become a stand alone venue in itself opening its stages to theater, music, comedy, visual arts, and spoken word performances along with community focused education workshops.
14 Castle St, Great Barrington,
MA 01230
With the historic Berkshire Theater as its muse and screen, the Mahaiwe Performing Arts Center offers performance, film, and cultural events year round for everything from ballet, opera, renaissance era art balanced exclusive viewings of movies such as “Harry Met Sally” or “Star Wars.
380 State Road, Great Barrington, MA 01230
Ski Butter. Ski better. Located in Massachusetts, Ski Butternut is a family-friendly mountain offering skiing, snowboarding, and tubing. The resort provides lessons and equipment rentals for both skiing and snowboarding.
37 Corey Rd Hancock, MA 01237
Jiminy Peak is a premier New England ski destination, featuring exceptional snow, a welcoming, family-friendly environment, and night skiing. Conveniently located near New York City, Boston, Hartford, and Albany, the resort offers more than 45 skiing and snowboarding trails spread across 167 acres.
472 West Mountain Road, Lenox, MA 01240
Nestled within over 1,000 scenic acres in the Berkshires, Pleasant Valley offers a diverse network of trails that meander through woodlands, meadows, wetlands, and up the slopes of Lenox Mountain, providing opportunities for hikes ranging from leisurely to challenging.
101 Dan Fox Dr, Pittsfield, MA 01201
A beloved winter gem, Bousquet Mountain boasts downhill skiing, tubing, snowboarding, lessons, camps, cross-country skiing trails and a terrain park in the winter plus hiking and live music in the summer out of their base restaurant, the LIFT Bistropub.
Richmond Mountain Rd, Lenox,
MA 01240
Starting in popular Kennedy Park, the Cliffwood Street Trailhead encompasses multiple trails for every skill level among the rich forestry and rolling hills complete with gazebos, benches, and scenic view points throughout.
472 W Mountain Rd, Lenox,
MA 01240
Pleasant Valley Wildlife Sanctuary encompasses 1,000 lush acres in the Berkshires, the ideal destination for hiking, exploring, bird watching, snow-shoeing, and maple sugaring.
14 Castle St, Great Barrington,
MA 01230
Copy: Starting in popular Kennedy Park, the Cliffwood Street Trailhead encompasses multiple trails for every skill level among the rich forestry and rolling hills complete with gazebos, benches, and scenic view points throughout.
11 Housatonic St, Lenox, MA 01240
A bookstore with a wine bar, do we really need anything else? A local staple, you don’t miss the chance to wander the expansive shelves, visit the Shade Gallery, or grab a glass of local wine from their bar which is open whenever the bookstore is - seven days a week.
91 Pittsfield Road, Lenox MA 01240
The Arcadian Shop has been a leader in the outdoor industry since 1974 and has everything you need to stay warm, cool, and safe in your adventures by blending fashion and function. From base layers to heli-skiing, this one-stop shop is a can’t miss.
4 Housatonic St, Lenox, MA 01240
Nestled in downtown Lenox, the name says it all but doesn’t scratch the surface of the treasures you’ll find when you open the doors. The encompassing collection of hand-made jewelry, international and locally made chocolates, and art are designed to entice your senses.
26 Housatonic St suite b, Lenox,
MA 01240
Dangerous in the best way, happy shoppers report that they have everything you want for yourself, guests, family, and friends. But especially everything you want for yourself. Fall in love with the trinkets, tokens, and treats at this locally-owned business.
420 Stockbridge Rd Unit 4,
Great Barrington, MA 01230
Barrington Brewery has been serving their own barn brewed beer since 1995, and since then has expanded their tap offerings beyond their award winning IPAs. Try something unique like their Raspberry Ale or cask-conditioned Ice Glen, and don’t miss out on their cheddar ale soup, Plowman’s Lunch, and chocolate stout cake from their on-site restaurant.
508 Canaan Road, Route 295,
Richmond MA 01254
Hilltop Orchards provides the best of both worlds with both wine and hard-cider tastings along their expansive orchards and vineyards. Apple picking is a must in the fall, but their jams, jellies, syrups, and picnics make the perfect companion.
4 Housatonic St, Lenox, MA 01240
The aromas of fresh bread will be your guide to this breakfast and lunch spot. Flaky croissants, traditional French omelets, oatmeal with brown sugar and roasted pears, and their robust salads highlight exactly where their ingredients come from using only the best and freshest available to accompany their impressive wine list.
391 North Street, Pittsfield
MA 01201
Their signature in terms of service is to create “a parallel universe where all the world’s problems are solved through belly laughs, love, edible and quaffable works of art” and any visiting patrons find that to be deliciously true. Elevating classics like pigs in a blanket, fusion dishes like Korean Kimchi Mandoo with their charcuterie boards or their kimchi reuben sandwich, paired with craft cocktails and biodynamic wines make this spot unmissable in Lenox.
52 Housatonic St, Lenox,
MA 01240
Located in the heart of downtown, Lenox Yoga has classes for every style and flow, including candle-light yoga, and offer drop-in rates for their classes as well as family sharing for their packages.
50 Castle St #2, Great Barrington,
MA 01230
A family friendly studio that encompasses fitness classes and wellness work-outs. You can find yoga classes, pilates, zumba, barre for all levels of expertise just down the road on Castle Street.
165 Kemble St, Lenox, MA 01240
165 Kemble St, Lenox, MA 01240 Copy: The interior is just as stunning as the palatial exterior at this pillared mansion, with a wide range of services curated for a variety of schedules. Spa services, nordic walks, pickleball, chair yoga, HIIT work-outs, cycling and low impact classes in their aquatic center leave you feeling rejuvenated and refreshed regardless of which you choose.
10 Willow Creek Rd, Lenox,
MA 01240
Take a one-hour train ride through the Hoosac Valley on a vintage rail car and get a front row seat to the mountainous expanse of the Berkshires. With the original station being built in 1905, they aim to not only preserve history, but make it while volunteer historians are there to feed your curiosity along the way.
5 Prospect Hill Rd, Stockbridge,
MA 01262
This public garden and historic home encompass 48-acres of natural splendor. Attend one of their tours, or explore on your own, but don’t miss the 8-acres of gardens including the world famous Blue Steps or the weekend high tea.
1040 Mass MoCA Way,
North Adams, MA 01247
The Massachusetts Museum of Contemporary Art is known for its stunning collection of both indoor and outdoor performing arts venues. They have long-term exhibitions throughout the property, and rotate through immersive, visual and gallery showcases for everything from world-renowned paintings, Sol LeWitt structures, and sound baths year-round.
104 Walker St, Lenox, MA 01240
Ventfort Hall was designed by architects Rotch & Tilden in 1893 for Sarah Morgan, the sister of J.P. Morgan. While called a “cottage,” the 28-room mansion is anything but, with the first floor open to the public and boasting an event schedule that includes live music and performing arts.
39 South St, Pittsfield, MA 01201
Situated in the center of Pittsfield, the Berkshire Museum brings together art, science, and history to ignite curiosity, foster innovation, and promote a passion for learning. With dynamic exhibits and changing collections that delve into the human story, a lively aquarium housing aquatic and reptile species, vibrant special events, and interactive programs for all ages, it offers endless opportunities for exploration and discovery.
9 Glendale Rd, PO Box 308, Stockbridge, MA 01262
The Norman Rockwell Museum highlights the influence of American illustration art in mirroring and shaping society while promoting timeless ideals of compassion, respect, and social justice, as depicted in Norman Rockwell's works.
55 Main St Unit B, Lenox, MA 01240
WAM Theatre is a professional theater company located in what is now called Berkshire County in Western Massachusetts, on the ancestral lands of the Mohican Tribe. It combines artistic expression with social activism, focusing on producing theater that promotes gender equity. Guided by its mission, WAM envisions theater as a form of philanthropy.
225 South Street Williamstown, Massachusetts 01267
Founded in 1950 by Sterling and Francine Clark, the Clark Art Institute opened in 1955 to showcase their art collection. Renowned for its intimate galleries and scenic surroundings, it combines a public museum with academic programs and a major art history library. As a global hub for art research and discussion, the Clark evolves through ongoing acquisitions and collaborations with contemporary artists and historians.
27 Church Street. Lenox, MA 01240
Located in Lenox, in the culturally rich Berkshire Hills, The Wit Gallery has been a premier contemporary art venue since 1999. Short for Wonders in Time, it showcases diverse works from established and emerging artists, including paintings, glass, photography, and sculptures. The gallery aims to delight collectors with art that blends technical skill, innovation, and accessibility.
69 Church Street, Lenox MA 01240
Founded in 2011, this gallery specializes in contemporary photography and nurturing local and international artists through guidance, inspiration and master classes. With lectures, workshops, and an annually hosted artist series, the experience extends beyond the framed gallery masterpieces.
20 Elm St, Northampton, MA 01063
Free to all, the Smith College Museum of Art invites you to discover artworks from across periods and geographies from ancient Greece to contemporary video art. Famous pieces that call this gallery home are “The Portrait of the Artist, Seated at her Easel” by Amile-Ursele Guillebaud, “Flag for Nina” by Ree Morton, hand-carved pieces from the Shang dynasty, Cathedral at Rouen” by Claude Monet, and original graphite sketches from Vincent van Gogh.
92 Hawthorne Street, Lenox
MA 01240
Original home of abstract artists George L.K. Morris and Suzy Frelinghuysen is set on a 46-acre estate and showcases their paintings, frescoes, and sculptures as part of their collection of American and European influenced cubist art.
