Top 7 Backpacking Trips in Massachusetts

Backpacking in Massachusetts offers a diverse range of landscapes, from rugged mountain ridgelines to tranquil forests and serene lakes. Whether you’re looking for a challenging multi-day trek through the Berkshires or a leisurely journey along historic trails near Boston, the state provides plenty of options for outdoor enthusiasts. With well-maintained long-distance routes, scenic summit views, and backcountry campsites, Massachusetts is an underrated yet rewarding destination for backpackers. Below are seven of the best multi-day backpacking trips in Massachusetts, ranging from weekend getaways to week-long adventures.

Featured Photo: Great Meadows Natural Wildlife Refuge (photo by Tim Bouwer)

Mount Greylock

Mount Greylock is home to the highest peak in Massachusetts at 3,491 feet, offering breathtaking views from the summit. The “Greylock in the Round” loop is a 14-mile trek featuring varied terrain, from rocky ascents to wooded valleys. The Appalachian Trail runs through the reservation, making it a great addition for those looking to extend their trip. Two backcountry shelters along the route provide overnight options, making it a beginner-friendly yet rewarding backpacking trip. In the fall, the foliage is spectacular, adding to the area’s scenic beauty.

Midstate Trail

Stretching 92 miles from the Rhode Island border to New Hampshire, the Midstate Trail takes hikers through rolling hills, farmlands, wetlands, and dense forests. The trail is well-marked and passes through Wachusett Mountain, offering a scenic climb with panoramic views of the state. While there are no official backcountry campsites, primitive camping is possible in certain areas with permission. The terrain is moderate, making it an excellent choice for those looking for an extended trek without extreme elevation changes. This is a great long-distance option for those wanting solitude and a diverse New England landscape.

Featured Photo: Wachusett Mountain (photo by MA Office of Travel & Tourism)

Appalachian Trail - Massachusetts Section

The Massachusetts portion of the famous Appalachian Trail covers approximately 90 miles and offers a perfect blend of rugged mountains, peaceful lakes, and historic landmarks. This section includes Mount Greylock, the highest point in the state, and picturesque Goose Pond, a great overnight spot for swimming and camping. Backpackers will encounter well-maintained shelters and campsites, making logistics easier for an extended trip. The trail is moderately difficult, with a few challenging climbs balanced by flatter, easier sections. This is an excellent option for hikers looking to experience a piece of the iconic AT within a week-long trip.

Metacomet-Monadnock Trail

Covering 114 miles, this trail runs from the Connecticut border up to Mount Monadnock in New Hampshire, crossing ridgelines, forests, and scenic summits. The route offers a mix of exposed ledges with stunning views, as well as deep, shaded woodlands. Highlights include the Holyoke and Mount Tom Ranges, which provide challenging yet rewarding climbs. Water sources and shelters are limited, so careful planning is essential for a multi-day trip. The trail is a great option for those looking for a long, uninterrupted hike with fewer crowds than the Appalachian Trail.

Tully Trail

A hidden gem in north-central Massachusetts, the 22-mile Tully Trail is perfect for a weekend backpacking getaway. The route loops through the scenic Tully Mountain, Royalston Falls, and Long Pond, providing a variety of landscapes from waterfalls to rocky summits. Several primitive campsites and shelters along the way make overnight stays convenient. The trail is moderately difficult, with some steep sections, but it’s manageable for most experienced hikers. This is a fantastic option for those looking for a short, immersive backcountry experience without venturing too far from civilization. Head over to our full write-up on the Tully Trail to get all the details.

Featured Photo: Tully Trail (photo by John Huynh)

Bay Circuit Trail

The Bay Circuit Trail is a 200-mile route that forms a greenway around Greater Boston, passing through forests, wetlands, and suburban landscapes. Since it passes through various parks and reservations, you can customize your trip by selecting 30-50 mile sections to complete over a few days. The trail is mostly flat, making it accessible for hikers of all levels, though logistics can be challenging due to limited camping spots. Popular sections include Walden Pond, Harold Parker State Forest, and Great Meadows Wildlife Refuge. This is a great trip for those wanting a mix of backcountry and urban-adjacent hiking.

The Berkshires

Western Massachusetts’ Berkshires region is home to some of the best backpacking in the state, with various trails offering multi-day hiking opportunities. The Appalachian Trail crosses through the region, but other excellent options include Mount Washington State Forest and Beartown State Forest. These trails feature a mix of mountain ridges, deep woodlands, and tranquil lakes, making for a scenic and varied experience. Many of the trails have shelters and designated backcountry campsites, making planning easier. This region is ideal for those looking for a flexible, nature-immersive backpacking trip with plenty of options to explore.

Conclusion

No matter what part of the state you're in, you're sure to find a scenic and interesting trail. Have you hiked any of the trails on our list? We'd love to hear about them, or any others in the region, in the comments section below!