Condé Nast TravelerOct 19
The Best Things to Do in the Berkshires—and Where to Stay
Art, nature, and history make this an idyllic New England retreat—as long as you’re okay with missing the beach.
Has a collection of almost 1,000 original drawings and paintings.
25 things in this story
- Red Lion InnHotelDiscover the charm of the Red Lion Inn in Stockbridge, MA.
- Norman Rockwell MuseumMuseumHas a collection of almost 1,000 original drawings and paintings.
- Charcoal TrailTrailLeads to Olivia’s Overlook for a stunning vantage point.
- Elsewhere
- 33 MainHotelLenox, United StatesEach room has artistic flair; offers complimentary breakfast and cocktail hour.
- Prospect BerkshiresHotelEgremont, United StatesOpened in 2025 with 49 Scandi-inspired cabins on Prospect Lake.
- Little Cat LodgeHotelNew York, United StatesHas an alpine-chic-meets-motor-lodge vibe.
- The Inn at Kenmore HallHotelRichmond, United StatesA boutique hotel in a stately Georgian home.
- Tourists WelcomeHotelNorth Adams, United StatesAn iconic roadside motel given a woodsy, Scandi makeover.
- Doctor Sax HouseHotelLenox, United StatesA nine-bedroom property dating back to the Gilded Age.
- Walker Street MarketMarketLenox, United StatesA new design gallery with works from over 70 contemporary artists.
- Underwater WeavingPlaceLenox, United StatesMaker of mind bogglingly cool baskets.
- Berkshire GalleriesMarketGreat Barrington, United StatesA great stop for antiquing.
- Fluff AlpacaPlaceGreat Barrington, United StatesStocks cozy sweaters and throws, plus tailored pieces.
- One MercantilePlaceGreat Barrington, United StatesFeatures an eclectic selection of linens, soaps, and local gifts.
- SETTPlaceGreat Barrington, United StatesA kitchen goods store with high-quality dining and serving wares.
- FuelCaféGreat Barrington, United StatesA popular spot for breakfast sandwiches and coffee.
- SoCo CreameryIce cream shopGreat Barrington, United StatesLocal ice cream parlor with classic and less-common flavors.
- TanglewoodSightLenox, United StatesIt has been the summer home of the Boston Symphony Orchestra since 1937.
- Jacob’s PillowSightBecket, United StatesJacob's Pillow is a dance center, school and performance space located in Becket, Massachusetts, in the Berkshires.
- MASS MoCAGalleryNorth Adams, United StatesOne of the largest museums in the US, known for contemporary programming.
- Hancock Shaker VillageSightPittsfield, United StatesA wholesome, family-friendly affair with farm animals.
- Shaker MuseumMuseumChatham, United StatesA second destination dedicated to the Shakers' pursuits.
- Shaker OutpostSightPittsfield, United StatesHosting seasonal exhibitions.
- Monument MountainNature reserveGreat Barrington, United StatesOffers one of the best views of the Housatonic River Valley.
- Mount GreylockTrailAdams, United StatesHike up for a view of the Appalachian Trail; highest point in MA.