Berkshire Itinerary Trails

Follow these trails for ways to explore and discover fun of all kinds in the Berkshires. Mix and match to make your own perfect Berkshire itinerary.

Blue Vista Motor Lodge

Fireplaces to Chill By Trail

Fall and winter in the Berkshires are magical times of year. Imagine sipping local cider at a fire pit while the leaves fall, digging into a hearty meal by a cozy hearth, or treating yourself to wine and a book by a roaring fire in your own room. Traveling during the warm weather seasons? Many of these amenities are available year-round. The following are a few chill places to warm up on your next cool trip to the Berkshires.

Family Fun Trail

The Berkshires have just what you need, be it activity in the beautiful outdoors or participating in hands-on learning! No matter if you are a visitor or lucky enough to live here, there are plentiful activities to enjoy with family members of all ages.

Balderdash Cellars, photo by Great Sky Media. Courtesy of 1Berkshire.

Berkshires Brewery, Winery & Distillery Trail

No trip to the Berkshires is complete without a sampling of our region’s local libations. Try a cold craft brew, a crisp cider, small-batch spirit, or glass of boutique wine. The Berkshire mountains will provide the perfect backdrop to your sipping and toasting. Cheers!

Mount Greylock, credit Ruth Schneider Photography

The Barkshires Trail (or Should We say Tail)

In the Berkshires, we love dogs! Travelers with furry friends will find tail-wagging welcomes at many of our lodging properties, downtown shops, alfresco dining establishments, and even some of our cultural grounds. Follow this trail for a few stops that are sure to be Fido’s new faves.

Funded, in part, by the Massachusetts Office of Travel & Tourism

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