Fall Hiking in Boston: A Guide to the Best Trails Oct 23, 2023

Fall is the time to get outside and enjoy the colorful foliage. One of the best ways to do that is to hike! The Seaport is a short drive from some of New England’s prettiest hiking trails, and the region has a variety of terrains to offer. If you’re a nature enthusiast, here’s a guide to our favorite trailheads and hiking spots.

Leisurely Treks

Andover: Ward Reservation
Ward Reservation has over 12 miles of trails that take you through forests, meadows, and wetlands. As you explore the trails, you’ll come across serene ponds and bubbling streams with peaceful spots for reflection.

Ashfield: Bear Swamp
A true haven for wildlife enthusiasts, Bear Swamp is a sanctuary for animals like deer, moose, and even black bears. The trails here lead to picturesque waterfalls and scenic overlooks, giving you a taste of untouched nature.

Medfield: Noon Hill
Noon Hill is your destination for panoramic views without the strenuous climb. The trails here have varying difficulty levels, but the reward is a breathtaking view of the Boston skyline juxtaposed against the sprawling countryside.

Advanced Hikes

Milton: Blue Hills Reservation
Home to Norfolk County’s highest point, Blue Hills Reservation is a treat for those looking for a challenge. The Skyline Trail stands out—giving hikers sweeping views of the area. Another gem is the Ponkapoag Trail, which winds through dense woods and marshy lands.

Carlisle: Great Brook Farm State Park
With over 10 miles of trails, this park is a mosaic of forests, fields, and wetlands. For those seeking more advanced hikes, trails like the Great Brook Farm Trail and Bear Hill Trail have more rigorous climbs and descents.

Jaffrey, New Hampshire: Mount Monadnock
Though a bit further out, Mount Monadnock is worth the drive. Just over an hour from Boston, this mountain showcases nature’s grandeur. With a range of trails, novices and experts alike can find their perfect path here.

For more information about hiking grounds around Boston, visit the Trustees site for their recommendations on Fall Foliage Hikes.