Exploring The Berkshires

Hiking,  Biking, Kayaking and more

The Berkshires are known for their beautiful trails and scenic landscapes. You can reach hiking and biking trails of varying difficulty levels from East Rock Inn, such as the Appalachian Trail, Monument Mountain. and Mount Greylock. Bike the Ashuwillticock Rail Trail and Housatonic Bike Routes, or go white water rafting with Crab Apple Whitewater or Zoar Outdoor. For serenity on the water, book a canoe or kayak with Berkshire Canoe Tours or paddle along Canoe Meadows.

Museums, Galleries and Historic Sites

The Berkshires are rich in history and art. The W.E.B. Du Bois Boyhood Home, Edith Wharton's home—The Mount, and Hawthorne's House of Seven Gables are just a few of the historic sites you can visit. The Norman Rockwell Museum, The Clark Institute, and Mass MOCA (Museum of Contemporary Art) contain permanent and rotating exhibits as well as educational and compelling programming. Go gallery hopping among the many art galleries lining Great Barrington's streets and discover new artists. You may be inspired to bring some art home with you.

Winter Sports: Skiing, Snowboarding, Tubing

The Berkshires provide many ways to enjoy the outdoors all winter. East Rock Inn is just one mile from Butternut Ski Area, where you can downhill ski, snowboard, and go snow tubing.  You'll also find Catamount Mountain Resort, its 44 trails less than 10 miles away, and Jiminy Peak ½ hour north. Head to Notchview for cross-country skiing and snowshoeing (there's even a dog-friendly loop!). And Canterbury farm in nearby Becket has cross-country ski trails and dedicated snowshoeing trails with a summit view of Mount Greylock. There's ice skating on their pond too!  Many of the local hiking trails become snowshoeing trails in the winter, providing a different views and vistas as the seasons change.

Music, Dance and Theater

Visitors flock to the Berkshires every summer for Tanglewood Music Center's outdoor concerts. The summer home of the Boston Symphony Orchestra (BSO), classical music dominates the schedule, but they also feature a popular artists series which has included James Taylor, Brandi Carlile, John Meyer, John Batiste, and more. There's nothing quite like listening to talented musicians play under the stars. Grab a picnic and a blanket and enjoy this Berkshires institution. Jacob's Pillow is where you'll find innovative dance performances. The Barrington Stage Company and Shakespeare & Company put on engaging plays and musicals. Check out the Mahaiwe Performing Arts Center in Great Barrington for an eclectic mix of theatrical programming all year.

Housatonic River Walk

The Housatonic River Walk is a scenic path along the Housatonic River, starting in downtown Great Barrington. Explore the beauty of the Housatonic River on this greenway gem, built by volunteers. You can even sign up for guided tours at https://gbriverwalk.org/. It's an unexpected and gorgeous addition to any Downtown Great Barrington itinerary and a beautiful way to take in some nature while shopping, eating, and enjoying the town.

Local Breweries and Wineries

Sip, savor, and say a toast to the craft breweries, wineries, and distilleries producing local Berkshires artisanal brews and spirits. From wine and cider tastings at Furnace Brook Winery to handcrafted beers at Barrington Brewery just up the road from East Rock Inn, you'll be sure to discover your new favorite libation. (Click here for more winery and brewery recommendations)