There's nothing like hiking in the Berkshires. From gorgeous peaks to canopied trails teeming with New England wildlife, the trails unfold to reveal wonder after wonder. In addition, hikers will find that many trails are perfect for dogs in the Pittsfield area. Here's a look at the five best dog-friendly hikes near Pittsfield, MA.

Shaker Mountain Trailhead
Situated along U.S. Route 20 on Lebanon Mountain Road in Hancock, MA, this popular trail covers parts of Pittsfield State Forest. Enjoy a two-track trail that winds through a forest of small trees before hitting a glistening reservoir on this 5.4-mile loop. There's an old Shaker settlement and Shaker Mountain for hikers who trek past the reservoir. While walking a dog, expect to see other people mountain biking or exploring the trails by horseback.
Lulu Cascade to Berry Pond
Located at 1041 Cascade Street in Pittsfield, the Lulu Brook Trailhead is part of Pittsfield State Forest. Visitors will find a beach with a picnic area that serves as a popular swimming hole for locals. Keep walking to discover the trailside waterfall at Lulu Cascade. The Lulu Brook Trail brings visitors along a 2.9-mile journey that winds along Berry Pond and Tilden Swamp. Ample parking is available for hikers on Berry Pond Circuit Road.

CCC Ski Lodge Trailhead
The CCC Ski Lodge Trailhead is located within the Pittsfield State Forest at 1041 Cascade Street in Pittsfield. A highlight of the trail is a 0.6-mile paved loop called Tranquility Trail, which is ideal for family hikes. As they make their way through the lush terrain, hikers are likely to hear songbirds. For hikers planning to go beyond Tranquility Trail, Turner Trail, and the Parker Brook Trail offer scenic upward journeys concluding with views of Tilden Swamp and Berry Pond.
Cheshire Harbor Trail, Bellows Pipe Trail
Part of Greylock Glen, the Cheshire Harbor Trail is found at West Mountain Road in Adams, MA. Visitors enjoy several trails that offer unique experiences and views during the changing seasons. The popular Cheshire Harbor Trail is a 6-mile stretch that leads to Mount Greylock's summit at an incline. At the top, hikers are treated to stunning panoramic views. There's also a small lodge selling food and drinks at the summit that welcomes hikers. For a more leisurely trek, the Moser Farm Loop weaves over small hills before reaching a lovely meadow offering views of towering Mount Greylock.

The Boulders
Offering one of the most scenic dog-friendly hikes near Pittsfield, MA, this stunning 6-mile trail offers dramatic boulders and vista views. Overall, the 645-acre scenic area surrounding this trail stretches across parts of Dalton, Lanesborough, and Pittsfield. While enjoying easy and moderate paths, visitors enjoy miles of terrain filled with sky-high trees and natural slopes.
Connecting With Nature Near Pittsfield: Start Planning Your Hike Today
There's nothing like sharing the beauty of nature with your pet! Pittsfield offers unforgettable trails and scenic views ideal for hiking with a dog. Whether you're chasing perfect photo spots at The Boulders or seeking stunning panoramic views near Mount Greylock, nature's beauty is waiting to welcome you to this refreshing portion of New England.