![]() ![]() With over 7,200 acres of state forest and hundreds of easily accessible trails only moments from the town’s center, visitors truly get to choose their own adventure. Dubois, and Edith Wharton called it home far before Meryl Streep visited) it’s pulsing with a revival that not only evokes appreciation for its long-standing appeal, but also an evolution that’s representative of our farm-to-table loving, environmentally conscious generation. Though it has over 250 years of history woven through it (the Berkshires are the birthplace of W.E.B. With a slew of new businesses that could easily thrive on a popular Brooklyn street-many of which actually did-and improvements to existing cultural institutions, Great Barrington has become one of the most popular destinations in the highlands of Massachusetts. While The Berkshires have persisted as a haven for nature-lovers and artists alike, in the last few years, it’s developed a new draw: young New Yorkers. “Part of the town’s appeal is that it’s not too reachable-getting here requires logistics and planning, so there’s a sense of successfully preserving what makes this place so special,” local travel consultant Rebecca MacGregor tells Vogue. The quaint brick town is just as charming as fictitious Starkfield, but with an artful undercurrent and cultural relevance that’s worthy of its two and a half hour drive from New York. While the masses flock to the Catskills, an upstate region that’s become a satellite community for Brooklyn weekend expats, you could head east of the Hudson River to the Southern Berkshires destination: Great Barrington. The difficulty-level of hiking here is relatively moderate, as there are plenty of inclines on the way up.In less time than it would take to read Edith Wharton's Ethan Frome, you could be having your own charmed experience in the Berkshires. This hiking destination has three main trails and a rewarding view at the peak. You can definitely make a day out of this somewhat small-but saturated-street.Ībout 10 minutes north of the Railroad Street shopping strip is Monument Mountain. Make sure you do not miss this side street if you are walking around Main Street in Great Barrington-which has its fair share of shops as well. Multiple other locations including clothing retailers, a toy store, eateries, and other art galleries fill the street with fun activities. There’s also Community Access to the Arts (CATA), located around the bend in Railroad Street, celebrating the artistic creativity of those with disabilities. Down the road a bit further, Iris Gallery showcases a range of fine art for the public to enjoy. They have tons of all-natural and flavorful ice cream year-round. One of the first shops on the left is SoCo Creamery. The 20 Railroad Public House serves local, sustainable, and responsible fare. The list goes on. The Triplex Cinema is a great place to watch independent films as well as some bigger hits occasionally. Crystal Essence has “a gallery of wonders” from crystals of all sizes to abstract trinkets and jewelry. Bizen is home to a delicious sushi bar and has spectacular Japanese cuisine. These local businesses are unique and cater to an array of experiences. Off of the Main Street shopping strip in Great Barrington, Railroad Street is packed with a variety of entertaining places to visit ranging from eateries to clothing retailers. ![]()
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