Located in Southwest Massachusetts, Great Barrington is the center of gravity in the state’s Berkshire Mountains. Surrounded by the rolling green peaks of that range, as well as the Housatonic River, Great Barrington is the quintessential New England trail town, thanks not only to its proximity to the Appalachian Trail, but as a hub of hiking, backpacking, biking, and more. The town of 7,000 residents also features a quaint downtown full of small shops and restaurants, so once the adventures are over, it’s easy to make a weekend out of a visit.

The view from Flag Rock. | Credit: Kristen Fielder


Hiking opportunities are plentiful with trails for all ability levels. Monument Reservation, on the north end of town, offers options for moderate hikes including Flag Rock and Monument Mountain. Or head to Beartown State Forest for more family friendly options. If you’re looking for more challenging hikes, hit the Appalachian Trail in either direction. Going north on the trail allows for an 8.9-mile out-and-back to East Mountain. Going South offers a 10.4-mile out-and-back to Jug End. Either way you’re looking at some of the best hiking on the Massachusetts stretch of the famed trail, surpassing even that of Mount Greylock.

The summit of Jug End. | Credit: Kristen Fielder


If you want to take it up a notch, turn your day hike into an overnight. The Appalachian Trail will have shelter and campsite spots in both directions. A great option is heading South on the AT over Mount Race to Sages Ravine. The ravine has designated campsites on either side with reliable water sources and bear boxes to store your food. Mount Race is east facing, giving you the opportunity for a beautiful mountain-top sunrise.

Mountain Biking

The nearby Beartown State Forest offers great mountain biking options. The big trail in the park is the black-rated Beartown Loop. The trail is four miles long but intersects at multiple points with other biking trails giving you the option of choosing your own adventure and tailoring your ride to the length and difficulty level of your choosing.


Great Barrington can’t be talked about without mentioning its swimming holes. The closest option is Lake Mansfield, less than a mile from downtown, however, for more quiet and solitude, head to either Benedict Pond in Beartown State Forest or Lake Mansfield on the Western edge of town.

Butternut Ski Resort. | Credit: Kristen Fielder

Winter Activities

Great Barrington isn’t limited to warm weather activities; it’s also a popular skiing and snowboarding area. Butternut Ski Resort is one of the top rated in the state with 22 ski trails. It also offers both private and group lessons with four ability levels from beginner to advanced. If skiing or snowboarding isn’t your jam, the ski resort also offers snow tubing for some low-key winter fun.

A selection from Patisserie Lenox. | Credit: Kristen Fielder


Make sure you start your day off with a coffee from one of the local coffee houses. Fuel Bistro, Marjoram and Roux, and Patisserie Lenox are your top options all with a different and distinct feel. Marjoram and Roux offers prepared food and a few outdoor tables on the quieter Railroad Street. Fuel Bistro has an earthy vibe, the largest food menu of the three, and potentially the best mocha around. Lastly is the French styled Patisserie Lenox. Do not leave Great Barrington without trying something—anything—from their pastry case.

When you’re ready for a heartier meal after a great day of outdoor fun there’s a plethora of restaurants to choose from. For the best sit down experience, Café Adam is not to be missed. Their changing menu is locally and ethically sourced and, during growing season, they harvest their own herbs and berries on premise. A more casual option is the Marketplace Kitchen Table which offers standard American staple food that you can get for take-out or dine in. If you’re a  burger lover, make sure to stop by The Bistro Box, a burger stand with the best burgers around that closes in the off-season.

Downtown Great Barrington. | Credit: Kristen Fielder


Most American downtowns have cute local shops and Great Barrington is no exception. I’d recommend making a stop at Yellowhouse Books, whether you consider yourself a reader or not. The store has a section with books on the area itself as well as a travel and outdoors section with unconventional memoirs and books that you’ll never find in your standard chain store. Just make sure you close the door when you enter and exit so the cat doesn’t get out.

Checking out a farmers market is also a popular activity for the town. There are a couple in the area that run at different times June through September.

Final Note

Make sure to check the hours of the places you want to go ahead of time. While Great Barrington is mostly up and running again since the pandemic, there are still some places that have limited hours or are closed some days during the week.