From quick and easy loops around town to drives that take you to fantastic lakes and mountains, our city has so many options to hit the trail. So lace up your hiking boots, because we’ve compiled a hiking guide for the Boston area with 15 routes and trails to help you plan your next adventure and experience breathtaking views.
Note: While parks and trails may be listed as open, we recommend checking park websites before visiting for further info, current trail conditions, and safest practices for the area.
Key: Easy = 🥾| Moderate = 🥾🥾 | Hard = 🥾🥾🥾
North of Boston
Battle Road Trail, 174 Liberty St., Concord
- Difficulty: 🥾
- Length: 5 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
The historic trail at Minute Man National Historical Park connects sites from Meriam’s Corner to Lexington. The route follows remnants of the Battle Road, the site of the first Revolutionary War battle on April 19, 1775 (and the shot heard ‘round the world).
Minute Man National Historical Park is home to several battle sites, including Concord and Lexington.
Photo by @boston1c
Walden Pond State Reservation, 915 Walden St., Concord
- Difficulty: 🥾
- Length: 1.9 miles
- Wheelchair accessible: Yes
- Pet-friendly: No
Spend a Thoreau-ly perfect day at the famous Concord reservation. The hike takes about ~40 minutes to complete as you encounter swimming beaches, forests, and birds.
Saugus River Trail, 177 Forest St., Saugus
- Difficulty: 🥾🥾
- Length: 2 miles
- Wheelchair accessible: Portions
- Pet-friendly: Yes
Visit the 652-acre state park, Breakheart Reservation, and hike up to the vistas for sweeping views of Boston, New Hampshire, and central Massachusetts. This more secluded trail will bring you by the water and take about ~45 minutes to complete.
Ipswich River Wildlife Sanctuary Trail, 87 Perkins Row, Topsfield
- Difficulty: 🥾
- Length: 3.5 miles
- Wheelchair accessible: No
- Pet-friendly: No
Visit between dawn to dusk to complete this easy route. It’s one of 12 trails at the sanctuary managed by the Massachusetts Audubon Society. Pro tip: This is one of the best nearby trails for avid bird watchers, as its home to a wide array of wildlife and birds.
Skyline Outer Reservoir Loop, 4 Woodland Rd., Stoneham
- Difficulty: 🥾🥾
- Length: 7.7 miles
- Wheelchair accessible: No
- Pet-friendly: Yes
Head to Middlesex Fells Reservation to try this popular loop out of four total trails. Bring your pups along, but be sure to follow the guidelines for dogs in on-leash and off-leash areas.
You can also bike, fish, or rent a canoe at Middlesex Fells Reservation.
Photo by @mr._thunderr
South of Boston
Great Blue Hill via Skyline Trail, 695 Hillside St., Milton
- Difficulty: 🥾🥾
- Length: 3 miles
- Wheelchair accessible: No
- Pet-friendly: Yes, leash required
The Blue Hills Reservation is one of the most popular hiking spots in close proximity to Boston (and when you catch the views of the skyline from Eliot Tower, you’ll know why). Pro tip: Bring a trekking pole to help with your footing in steep areas.
World’s End Trail, Martin’s Lane, Hingham
- Difficulty: 🥾🥾
- Length: 3.8 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
Hike the area in between Hingham Harbor and the Weir River for coastline charm along the Frederick Law Olmsted-designed paths. The trail is open year-round and takes about 1 hour and 23 minutes to complete.
World’s End comprises four coastal drumlins, aka spoon-shaped hills formed by glaciers.
Photo by @tessavirginia_photography
East Head Reservoir Trail, 194 Cranberry Rd., Carver
- Difficulty: 🥾
- Length: 2.7 miles
- Wheelchair accessible: No
- Pet-friendly: Yes, leash required
Known as a go-to camping and swimming destination for families, Myles Standish State Forest is the largest publicly owned recreation area in this part of Massachusetts. There are 13 miles of hiking trails to explore — the East Head Reservoir Trail takes about 60-90 minutes to complete.
Cape Cod Rail Trail, 3488 Main St., Brewster
- Difficulty: 🥾
- Length: 27.6 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
Also a popular biking destination, Nickerson State Park is open from sunrise to sunset, with multiple parking and trailhead options available. The route leads hikers through six Cape Cod towns, including South Yarmouth and Dennis.
West of Boston
Charley’s Loop Trail, 198 Purgatory Rd., Sutton
- Difficulty: 🥾🥾
- Length: 1.7 miles
- Wheelchair accessible: No
- Pet-friendly: Yes, leash required
Purgatory Chasm State Reservation is home to two miles of trails along the sites of ancient rock formations. Don’t miss Purgatory Chasm itself, a quarter-mile long formation that runs ~70 ft high.
Check out The Corn Crib, The Coffin + Lovers’ Leap rock formations at Purgatory Chasm State Reservation.
Photo by @rankinphotography
Balance Rock Loop, 345 Mountain Rd., Princeton
- Difficulty: 🥾🥾
- Length: 4 miles
- Wheelchair accessible: Portions
- Pet-friendly: Yes, leash required
Take the ~one hour drive from Boston to see views from Wachusett Mountain State Reservation, the tallest mountain near our city. The reservation is home to 17 miles of hiking and walking trails and Massachusetts residents pay $5 to park from May 15 through November.
Mount Greylock via Bellows Pipe, 30 Rockwell Rd., Lanesborough
- Difficulty: 🥾🥾 🥾
- Length: 5.9 miles
- Wheelchair accessible: Portions
- Pet-friendly: Yes, leash required
The highest point in the Bay State covers ~12,000 acres of Lanesborough, North Adams, Adams, Cheshire, Williamstown, and New Ashford. On a clear day, you can see up to 90 miles away from the summit.
The tallest mountain in Massachusetts, Mount Greylock, is 3,491-ft high.
Photo by @macsadventure
Boston
Freedom Trail, Boston Common
- Difficulty: 🥾
- Length: 2.5 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
This brick-lined route leads you to 16 sites significant to the American Revolution, including meeting houses, churches, and burying grounds. If you’ve never taken the trail before, start at the Boston Common and make your way to the USS Constitution Museum.
While you walk the Freedom Trail, admire Boston’s oldest surviving church building.
Photo by @embarkthepark
Charles River Southwest Corridor Trail, Charles River Reservation
- Difficulty: 🥾
- Length: 4 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
Enjoy views of that “Dirty Water” with an urban hike around Cambridge, crossing over the Boston University and John F. Kennedy Street bridges.
Arnold Arboretum Trail, 125 Arborway
- Difficulty: 🥾
- Length: 3.7 miles
- Wheelchair accessible: Yes
- Pet-friendly: Yes, leash required
This nature sanctuary in Jamaica Plain hosts a variety of walks and tours around the property, including this ~one-hour long loop. Pro tip: Find free parking along the Arborway, Bussey Street, and Walter Street.
