In the area


The scene at Tanglewood.


link-dark297 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.


The Foundry

link-dark2 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.



link-dark14 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.

Outdoor Recreation

Bousquet Mountain

Bousquet Mountain

link-dark101 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.

Scenic view

Cliffwood Street Trailhead

link-darkRichmond 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.


Pleasant Valley Wildlife Sanctuary

link-dark472 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.


Wyndhurst Golf &Club

link-dark14 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.


Book Library

Bookstore & “Get Lit” Wine Bar

link-dark11 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.


Arcadian Shop

link-dark91 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.

Art & Chocolate

Art & Chocolate

link-dark 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.

Wilcox & Co.

Wilcox & Co. 

link-dark26 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.



Barrington Brewery & Restaurant

link-dark420 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.

Houses with huge field

Hilltop Orchards

link-dark508 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.

Alta Restaurant & Wine bar


link-dark 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.


Methuselah Bar & Lounge

link-dark391 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.

Relaxation & Wellness

Lenox Yoga

 Lenox Yoga

link-dark52 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.

Girls doing Yoga

Life Works Studio

link-dark50 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.

Swimming Pool

Canyon Ranch Spa

link-dark165 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.

Tours & Exploration

Train over bridge

Berkshire Scenic Railway

link-dark10 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.


Naumkeag House & Gardens

link-dark5 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.

Art Gallery


link-dark1040 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.

Vintage house

Ventfort Hall Mansion & Gilded Age Museum

link-dark 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.

Art Galleries

Art Gallery

Sohn Fine Art

link-dark69 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.

Art Gallery

Smith College Museum of Art

link-dark20 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.

White room with stairs

Frelinghuysen Morris House & Studio

link-dark92 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.