Because there’s no better way to take in the breathtaking beauty of New England’s nature than going hiking in autumn!
It’s safe to say Boston’s one of the best and most beautiful cities in the country, but our beloved Beantown is also surrounded by some absolutely stunning wilderness. From the more urban Emerald Necklace to the hilly paths of World’s End, explore the great outdoors at these ten gorgeous hiking spots near Boston, perfect for hikers of all levels. Oh and don’t forget to bring your camera with you because these gorgeous trails serve some equally enchanting views!
One of these hikes was even named among the top 5 in the country according to The Broke Backpacker. Scroll all the way down to find out which one!
1. Battle Road Trail; Concord, MA
If you’re a history buff with a penchant for hiking then we suggest trying out Battle Road Trail. The pathway follows the route of the Minutemen as they moved from their first skirmish with the British troops, connecting multiple historic sites all the way from Concord to Lexington. The trail is more of a relaxed walk than an altitude hike but it’s perfect for learning some local history while enjoying some pretty stunning views!
Find Battle Road Trail at
2. Blue Hills Reservation; Milton, MA
This natural park just 20 minutes outside of Boston offers more than 120 miles of trails for hikers of all levels. If you’re up for the challenge the six-mile Skyline Loop offers extensive boulder climbing and hiking uphill, but the views of Boston’s skyline that wait for you at the end are seriously stunning. Other trails at the Blue Hills Reservation will also take you through archeological sites including some with evidence of Native American tribes and other remnants of early farms and quarries.
Find Blue Hills Reservation at 695 Hillside St, Milton, MA 02186
3. Breakheart Reservation; Saugus, MA
This 640-mile reservation, unknown to many, loops around a wild section of the Saugus River, north of Boston. Counting two lakes, Breakhearts trails are a popular destination for hikers during the warmer months. Its outcrops are just over 200 feet in height, offering gorgeous views of Boston and southern New Hampshire.
Find the 652-acre reservation at 177 Forest St, Saugus, MA 01906
4. Emerald Necklace; Boston, MA
Not technically a hiking trail but still gorgeous nonetheless, and it’s right in the heart of Boston! Created more than 100 years ago, this path connects up to 1,000 acres worth of parks all the way from Boston Commons to Franklin Park. While you can walk the whole 7 miles in one go, you can also take it by stages and enjoy some of the many attractions you’ll find along the way such as our famous Swan boats, the Fenway Victory Gardens, and the Arnold Arboretum.
Find the Emerald Necklace at 125 Fenway, Boston, MA 02115
5. Halibut Point State Park; Rockport, MA
Just off Rockport’s historic hotel, The Emerson Inn, you’ll awe at Halibut Point’s 2.5 miles of gorgeous, rocky trails that will take you right down to the ocean. Bird watchers will find this particular trail appealing since its rocky terrain covered in bayberry and shad provides an excellent habitat for small birds.
Find the State Park at 0 Gott St, Rockport, MA 01966
6. Mount Misery; Voluntown, CT
Don’t let its name deter you, Mount Misery is actually quite hiker-friendly! Its trails make for an easy, relaxed walk or even a run, with only a 232-foot incline, you will be anything but miserable. Plus, They’re also great for going on a walk with your furry friends!
Find Mount Misery Trail in Voluntown, CT
7. Mount Monadnock; Dublin and Jaffrey, NH
Mount Monadnock offers an absolutely stunning reward for those willing to work for it. It has well over 30 trails to pick from. Although shorter than most of the other hiking trails on our list, this trail requires some serious scrambling and some steep passages to reach the top of its 3,166-foot elevation, but it also has some really stunning views of the New England wilderness once you make it to the summit!
Add Mount Monadnock to your GPS at let the adventure begin!
8. Mount Wachusett; Princeton, MA
The tallest mountain near Boston, Mount Wachusett offers great views of the skyline, Mt. Monadnock in New Hampshire, and the Berkshires in west Mass on a clear day. At the 3,000-acre Wachusett Mountain State Reservation surrounding the summit, you’ll find 17 miles of walking and hiking trails perfect for all levels of experience.
Find Mount Wachusett at 499 Mountain Rd, Princeton, MA 01541
8. Stony Brook Reservation; Boston, MA
This small forest located in the city offers several different activities including fishing, canoeing, cross-country skiing, and of course hiking. Its 12 miles of trails are a perfect destination for those who don’t want to venture out of Boston but still want to get lost in nature.
Find Stony Brook Reservation at 95 Turtle Pond Pkwy, Hyde Park, MA 02136
9. World’s End Reservation; Hingham, MA
Like Stony Brook, World’s End has an activity for everyone including biking, horseback riding, or canoeing. Its winding trails, follow the shores of saltwater marshes across woodlands and meadows which play an important part as habitats for the local fauna and flora. Wander along its beautiful hills and enjoy gorgeous views of the Boston Harbor Islands and the city skyline.
Find World’s End Reservation at 150 Martins Ln, Hingham, MA 02043
10. Mount Katahdin; Millinocket, Maine
Maine’s tallest mountain, Katahdin is a legendary destination that features blazing Appalachian trails where hikers begin or finish their journeys. It was recently ranked the fourth best hiking destination in the USA according to The Broke Backpacker. The incredibly steep drops along Knife’s Edge Trail make this hike suited to the experienced only, but you can take baby steps by testing out one of the less intense hikes above first.
The nature here is extremely guarded by keepers of the Baxter State Park, where the mountain sits, which means they strictly limit the number of vehicles parked on the reservation. Make sure to reserve a spot for your vehicle in advance, otherwise, you might just get deserted on Mount Katahdin.
Find Mount Katahdin at Maine’s Baxter State Park