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Massachusetts Backpacking Trails

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.

New York City, NY: Alander Mountain

Tag three mountains, including the highest point in Connecticut, on this 12.1-mile hike in Mt. Washington State Forest. Attractions include: pretty streamside camping, spectacular ridgeline hiking, fine mountain views, and a bounty of blueberries.

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: 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: 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 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.

Albany, NY: Mount Greylock

Lazy folks drive to the top. Be a champ and hike the 7.8 miles from farm fields and hardwood forests to the highest summit in Massachusetts.

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.

Albany: Mount Frissell

Stand in three states, then summit a wooded peak while passing the highest hill in Connecticut on this 4-mile dayhike in the Taconic Mountains.

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.

Appalachian Trail: Mount Greylock Hike

Hit this 15-mile out-and-back on the Appalachian Trail via train and bus for sprawling views and Massachusetts’ high point.

Springfield, MA: Mounts Everett and Race via Appalachian Trail

Connect the tops of two Berkshire peaks and catch views into three states on this 4.4-mile out-and-back in Mount Everett State Reservation.

Appalachian Trail: Jug End Road to MA 23

Exposed ledges, a glacial cleft, summit climbs, and a talus-strewn ravine highlight this 12.5-miler in the Berkshires and Taconic Mountains.

Appalachian Trail: Gulf Road to Cheshire, MA

Watch for black bears along this 7.1-mile leg that features woodlands and a worthy side trip to the glacial leftovers of Cheshire Cobbles.

Appalachian Trail: Pittsfield Road to Gulf Road

Go from wooded ravines to marshy bogs to a blueberry-speckled trail on this mellow 10.5-mile segment.

Appalachian Trail: I-90 to Pittsfield Road

Over the course of this 9.6-miler, you’ll crest three Berkshire peaks, cruise the banks of Finerty Pond, and visit the largest state forest in Massachusetts.

Appalachian Trail: Tyringham Road to I-90

Tour hemlock- and pine-covered landscapes in the Berkshires to a glacial lake nestled between wooded hills on this 8.4-miler.

Appalachian Trail: MA 23 to Tyringham Road

This 11-miler follows a network of bog bridges, passes a glacial pond, and showcases postcard views from The Ledges.

Appalachian Trail: Notch Road to VT 9

Earmark a long weekend for this 20.9-miler that connects Massachusetts to Vermont. Highlights include: sweet lookout views and a walk on The Long Trail–the country’s first long–distance trail.

Appalachian Trail: Cheshire, MA to Notch Road

Connect farm fields, hardwood forests and the rocky crown of Mount Greylock–Massachusetts’ highest summit–on this 10.9-mile dayhike.

Appalachian Trail: CT 41 to Jug End Road

Rocky and rugged, this 15.9-mile trek travels through two states, crests the tallest peak in Connecticut, and links four summits in Massachusetts.

Boston, MA: Charm Bracelet Trail

Link meadows to hilltops across Westborough’s open spaces.

Albany, NY: Mount Greylock via Stony Ledge

This 9-mile out-and-back charges up Mount Greylock, the highest peak in Massachusetts.

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.

State Highpoint: Mount Greylock via Bellows Pipe Trail

Take the 5.5-mile trek up Bellows Pipe Trail to the summit, while your there enjoy a local cocktail a cup of chowder at Bascom Lodge.

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.

Mt. Grace State Forest, MA: New England National Scenic Trail

Walk deliberately into woods filled with waterfalls and stone walls on this 23.6-mile point-to-point deep in Massachusetts’ Mt. Grace State Forest.

Massachusetts New York City

New York City, NY: Alander Mountain

Tag three mountains, including the highest point in Connecticut, on this 12.1-mile hike in Mt. Washington State Forest. Attractions include: pretty streamside camping, spectacular ridgeline hiking, fine mountain views, and a bounty of blueberries.

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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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