Our Story

Tails on the Trail . . .

Tails on the trail and wagging all the way—exploring the Berkshires one hike at a time.
Our story starts with a wag, a woof, and a whole lot of love. When we lost our sweet dog Mysty (pictured on the left), our hearts broke, but from that loss, something beautiful grew. BerkshiresTrails was born to celebrate the joy, laughter, and muddy pawprints she, and all our pets left behind.

This site is lovingly dedicated to our unforgettable furry (and feathered!) crew: Mysty, Montana, and Milly, best trail buddies; Comanche and Tiger, our purring partners in crime; Petey, our fearless hopping hero; and Elvis the cockatiel, who totally ran the show (and she knew it).

Mysty and Montana, chilling in the Berkshires!

Favorite Trail Stops

There’s so much to discover with these trail stops across the Berkshires, and we think you and your family will feel the same. Each town offers its own charm, character, and sense of place.

If you’re considering making the Berkshires your home, we’ve highlighted the places where we’ve lived ourselves with Williamstown as our first home base. And there’s no better way to understand a community than by walking through its neighborhoods, experiencing daily life, and seeing what it’s like to live in #intheberkshires.

Trail Stops: Adams, Alford, Becket, Cheshire, Clarksburg, Dalton, Egremont, Florida, Great Barrington, Hancock, Hinsdale, Lanesborough, Lee, Lenox, Monterey, Mount Washington, New Ashford, New Marlborough, North Adams, Otis, Peru, Pittsfield, Richmond, Sandisfield, Savoy, Sheffield, Stockbridge, Tyringham, Washington, West Stockbridge, Williamstown, and Windsor.

Dedicated to Berkshire Enthusiasts!

Below is a list of links that Berkshire Enthusiasts will find helpful. We wish y’all many #happytrails here in the Berkshires.

https://www.visitma.com/

https://berkshiresoutside.org/

https://thetrustees.org/

https://www.ustravel.org/

https://www.visittheusa.com/

https://massachusetts250.org/