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Trails Near Boston

White Mountain National Forest: Mount Madison

This steep 7.8-mile hike climbs through deep forest and alpine tundra to the summit of one of New Hampshire’s famed Presidentials for views as far as Maine.

Manchester, NH: Falling Waters-Old Bridle Path

Climb past cascading waterfalls, alongside rocky ledges, and over three exposed summits on this 7.8-mile loop, which offers some of the best views in the White Mountains.

White Mountain National Forest: Mt. Moosilauke

This 7.3-mile loop hike takes you up a steep, rocky trail to an exposed, treeless summit that’s the southwesternmost high peak in the White Mountains, and one of the prettiest.

Boston: Ispwich Water Trail

Paddle this 11.5-mile loop through open bays and protected salt marshes to beaches with giant sand dunes and historic buildings from the late 1700s.

Boston: Peddocks Island Paddle

Paddle to sandy sanctuaries, explore an old fort, and camp on the Boston Harbor Islands on this scenic 9.7-mile out-and-back to Peddocks Island.

Boston: Mt. Monadnock Loop

Hike 4.6 miles up the quieter, less-traveled west side on one of the mountain’s oldest trails, alternating between forested scrambles, old streambeds, and exposed rock ledges.

Boston: Skyline Trail to Cross Fells Loop

This 12.1-mile loop skirts five reservoirs, cuts through forests of oak, hemlock, and birch, and gains 2,600 feet of elevation in 2,060-acre Middlesex Fells Reservation.

Boston: Skyline Trail Loop

On this 6-mile loop in Blue Hills Reservation, you’ll see dense hardwoods, meadows, ponds, glacial leftovers,
rocky hills, and sweeping views of Boston.

Portsmouth, ME: Folly Pond Loop

Moose tracks outnumber boot tracks on this secluded 8.4-mile loop through rolling farmland to a wooded New England pond.

Boston: Wachusett Mountain Loop

This 5.8-mile loop takes you through a 400-year-old forest to summit the highest Bay State peak east of the Berkshires.

Manchester, NH: Mountain Trail

This gentle 4.8-mile climb strings through the thick woods of Pawtuckaway State Park to a fire tower lookout with four-star mountaintop views.

Boston, MA: Ponkapoag Pond Loop

This scenic 4.2-mile hike in the Blue Hills Reservation loops under pines and passes by a rare Atlantic white cedar bog, home to 17 endangered species.

Boston: Mount Monadnock

This 4.4-miler winds through mixed forest, ascends rock slabs, and climbs to an exposed summit with endless views of New England.

Boston: Alander Mountain Loop

Head up to a ridge overlooking the Hudson Valley and Catskills, and return through beaver and berry country.

Boston: Prospect Hill Loop

Hop off the bus for a 12.6-miler through red-maple swamps and old-growth forest filled with deer, grouse, and turkeys.

Boston, MA: Charm Bracelet Trail

Link meadows to hilltops across Westborough’s open spaces.

Boston, MA: North Skyline Trail

Take a ridgeline walk to views of the Boston skyline.

Boston, MA: Mt. Wachusett

Bag the highest Bay State mountain east of the Berkshires, a famous New England ski resort.

Boston, MA: Wompatuck State Park

Explore Wompatuck State Park on a labyrinthine trail system that showcases classic New England-style singletrack right outside Boston.

Boston, MA: Blue Hills Skyline Trail Loop

On this 6-mile loop in Blue Hills Reservation, you’ll see dense hardwoods, meadows, ponds, glacial leftovers,
rocky hills, and sweeping views of Boston.

Boston: Welch-Dickey Loop

Click off two 2,500-plus foot peaks, sample from entry-level scrambling on granite slabs on this 3.8 mile loop.

Boston New Hampshire

Boston: Mt. Monadnock Loop

Hike 4.6 miles up the quieter, less-traveled west side on one of the mountain’s oldest trails, alternating between forested scrambles, old streambeds, and exposed rock ledges.

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Boston Massachusetts

Boston: Skyline Trail Loop

On this 6-mile loop in Blue Hills Reservation, you’ll see dense hardwoods, meadows, ponds, glacial leftovers,
rocky hills, and sweeping views of Boston.

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