Welcome to the Berkshires! Come along with HUTS on our twenty-fifth Town Guide. This time around, we’re taking a quick dive into Stockbridge, Massachusetts. Known for its historical downtown, Stockbridge has quite the offerings for foodies, bookworms, and hikers alike.

Cover Photo by: Stockbridge Chamber of Commerce

Try out Tiffany’s Café at Elm Street Market! This hub of local life is located in the center of Stockbridge. The old fashioned butcher shop has been transformed to a lively café, and offers deli classics, including breakfast and lunch. Grab a bite to eat and don’t forget to pick up a snack for later in their grocery section.

What to do Outside

Just a pinch southeast of Stockbridge is Massachusetts’ Beartown State Forest. For our hikers, we definitely recommend trying out a trail or two. This 12,000-acre forest, open from dusk until dawn, also includes Benedict Pond, which is perfect for swimming, boating, or fishing. Whether you’re looking to set sail or be land-bound, Beartown State Forest offers it all.

What to do Inside

If you’re a reader, you’ll have to stop by The Bookloft. Independent since 1974, this book shop is sure to have your next great read on its shelves and even hosts events like author readings and scholastic nights.

The Bookloft even hosts book groups on a monthly basis, if you’re looking to have some friends hold you accountable on your reading goals. This massive bookstore is open from 10am-6pm Monday through Friday or until 5pm on Saturdays.

Where to Stay

Conroy’s Bed & Breakfast provides guests with a quaint and historical stay with the luxe addition of an outdoor pool. This bed & breakfast will have you feeling right at home with its pancake breakfast and hot coffee, ready by 8am. If you grabbed a new novel at The Bookloft, you’ll find the perfect place to read it under the dozens of maple trees on the bed & breakfast’s property.