By Sarah Rutledge

If you’re looking to…

Explore on your own
Winding roads, mountain trails, and rail-trail (car-free) trips—the Berkshires has it all. Berkshire Bike & Board, with locations in Great Barrington, Pittsfield, and Hudson, New York, is a great resource. They rent bikes and the expert staff offers advice and full-service maintenance. Can’t stop into a shop? You’ll find a wide range of routes on their website.
berkshirebikeandboard.com

Have an overnight adventure
If you’re up for something more rugged, book Tyler Burton of Hudson-based Lichen Bike Tours for a bikepacking trip, which combines cycling and camping. He’s done rides in Hillsdale and has tours coming up in the Catskills. Trips range from one to four days and cover up to 220 miles. Riders must carry their own shelter, sleep, and cook systems. For first-timers, Burton has a screening process to ensure they’re ready for the adventure.
lichenbiketours.com

Take a curated tour
Run by outdoors enthusiast Jenna Giardina, the brand-new Pittsfield-based Berkshire Adventure Tours offers e-bike rides curated around gorgeous terrain and fun stops, with offerings like Pedal to the Pub, an out-and-back ride on the Ashuwillticook Rail Trail with a stop at AJ’s Pub; Bikes and Boats, a hilly ride in Narragansett Park followed by a pontoon cruise; and Hill Top Wine Loop, a relaxing route around Richmond Pond with a stop at Hilltop Orchards. berkshireadventuretours.com