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Things To Do

The Berkshires is so special to us, and we can't wait to welcome all of you! Here is a list of our favorite spots to eat, hike, and make the most of your stay:

The Bistro Box

937 South Main Street, Great Barrington, MA 01230

Our favorite spot in the area for lunch and summertime snacks! We love the BOX Burger, Truffle Fries, and rotating Shakes. We recommend arriving by 11:30; longer lines can form.

No Comply Foods

258 Stockbridge Road, Great Barrington, MA 01230

The best brunch in the Berkshires (recently featured in Vogue and the NYT!). Menus rotate, but the Golden Milk Latte is a must order.

Railroad Street

Railroad Street, Great Barrington, MA 01230

Great Barrington's main street and shopping area! This is our buzzy town center, packed with local eateries and retail/vintage storefronts. Bop around or explore our favorite spots: Bizen for sushi, Ilse for coffee, Mooncloud for cocktails, and SoCo for ice cream.

Monument Mountain

Great Barrington, MA 01230

Our favorite hike for picturesque views! Moderate/accessible; 1.5-2.5 hours there and back (2.5-3.8 miles roundtrip). There are two starting points, but we recommend the Flag Rock Trailhead entrance for a true escape into the woods.

Benedict Pond Loop

Great Barrington, MA 01230

An easier-to-moderate 1.7 mile trail near Camp Yemc (The Prospect), offering scenic views and wildlife viewing opportunities!

Taft Farms

119 Park Street, Great Barrington, MA 01230

Our favorite farm stand! Taft Farm is best known for their Tangleberry Pie & bakery treats. For those who hike Monument Mountain: Taft Farms is across the street from the Flag Rock Trailhead and the perfect sweet treat after - you've earned it!