TOP 30 Scenic mountain trails in Great Barrington, Massachusetts

Monument Mountain Reservation is a park and tourist attraction located in Great Barrington, Massachusetts, United States. From the 1,642-foot summit of this popular peak, visitors can gaze across the splendor of the Housatonic River Valley. The mountain has been sacred to the Mohican people and their ancestors since ancient times, with stone offerings imbued with prayers left on the mountain creating the "monument" for which it is named. The original monument was destroyed by white residents after the Mohicans were dispossessed, but was later recreated near the Mohican Monument Trail. Monument Mountain has long inspired works of art and literature, with authors such as William Cullen Bryant, Nathaniel Hawthorne, and Herman Melville finding motivation for their works on the mountain. Today, more than 20,000 hikers ascend to its summit, Peeskawso Peak, each year. Three trails offer scenic ways to explore the mountain's pale quartzite geology and views out to Mount Greylock and the Catskill Mountains.

Monument Mountain Reservation/Flag Rock Trailhead Location: Great Barrington, Massachusetts 01230, United States Type: Park

Welcome to the Appalachian Trail at Deerwood Circle, a serene escape nestled in the heart of Great Barrington, Massachusetts. Located at Deerwood Circle, this picturesque park offers nature enthusiasts and adventurers alike a gateway to the stunning landscapes of the Appalachian Trail. Immerse yourself in the lush greenery and tranquil beauty that defines this historic trail, known for its breathtaking views and diverse wildlife. Whether you're a seasoned hiker or a casual walker, our park provides a variety of trails suitable for all skill levels. Enjoy a leisurely stroll through the gentle pathways or challenge yourself with more rugged terrain. Along the way, discover the rich flora and fauna that inhabit this unique ecosystem.