Massachusetts Trail Guides

Appalachian Trail Massachusetts Section

📍 Dalton

Hard 📏 12.0 Point-to-Point

Explore Appalachian Trail Massachusetts Section in Dalton, Massachusetts. A hard 12.0-mile point-to-point trail.…

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Appalachian Trail: Saddleback Mountain — Cheshire, Massachusetts

📍 Cheshire, MA

Hard 📏 4.0 miles Out-and-back

Appalachian Trail: Saddleback Mountain is one of Massachusetts's most rewarding hiking destinations, offering 4.0 miles …

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Bash Bish Falls Trail

📍 Mount Washington

Moderate 📏 1.5 Out-and-Back

Explore Bash Bish Falls Trail in Mount Washington, Massachusetts. A moderate 1.5-mile out-and-back trail.…

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Battle Road Trail

📍 Lexington

Easy 📏 5.5 Point-to-Point

Explore Battle Road Trail in Lexington, Massachusetts. A easy 5.5-mile point-to-point trail.…

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Beartown State Forest Trail

📍 Monterey

Hard 📏 8.0 Loop

Explore Beartown State Forest Trail in Monterey, Massachusetts. A hard 8.0-mile loop trail.…

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Blue Hills Reservation Great Blue Hill Trail

📍 Milton

Moderate 📏 5.5 Loop

Explore Blue Hills Reservation Great Blue Hill Trail in Milton, Massachusetts. A moderate 5.5-mile loop trail.…

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Blue Hills Skyline Trail — Canton, Massachusetts

📍 Canton, MA

Moderate 📏 8.5 miles Out-and-back

Blue Hills Skyline Trail is one of Massachusetts's most rewarding hiking destinations, offering 8.5 miles of challenging…

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Borderland State Park Trail

📍 North Easton

Moderate 📏 7.0 Loop

Explore Borderland State Park Trail in North Easton, Massachusetts. A moderate 7.0-mile loop trail.…

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Bradley Palmer State Park Trail

📍 Topsfield

Moderate 📏 6.0 Loop

Explore Bradley Palmer State Park Trail in Topsfield, Massachusetts. A moderate 6.0-mile loop trail.…

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Breakheart Reservation Loop — Saugus, Massachusetts

📍 Saugus, MA

Moderate 📏 3.5 miles Loop

Breakheart Reservation Loop is a 3.5-mile loop trail at Saugus, MA in Massachusetts, widely regarded as one of the most …

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Breakheart Reservation Trail

📍 Saugus

Moderate 📏 4.5 Loop

Explore Breakheart Reservation Trail in Saugus, Massachusetts. A moderate 4.5-mile loop trail.…

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Broad Meadow Brook Wildlife Sanctuary Trail

📍 Worcester

Easy 📏 2.5 Loop

Explore Broad Meadow Brook Wildlife Sanctuary Trail in Worcester, Massachusetts. A easy 2.5-mile loop trail.…

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Buffam Falls Conservation Area Trail

📍 Pelham

Moderate 📏 3.5 Out-and-Back

Explore Buffam Falls Conservation Area Trail in Pelham, Massachusetts. A moderate 3.5-mile out-and-back trail.…

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Buffumville Lake Trail

📍 Oxford

Easy 📏 4.0 Loop

Explore Buffumville Lake Trail in Oxford, Massachusetts. A easy 4.0-mile loop trail.…

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Cape Ann Loop Trail

📍 Rockport

Moderate 📏 5.5 Loop

Explore Cape Ann Loop Trail in Rockport, Massachusetts. A moderate 5.5-mile loop trail.…

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Cape Cod National Seashore Trail

📍 Wellfleet

Easy 📏 5.0 Loop

Explore Cape Cod National Seashore Trail in Wellfleet, Massachusetts. A easy 5.0-mile loop trail.…

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Chesterfield Gorge Trail

📍 Chesterfield

Moderate 📏 2.5 Out-and-Back

Explore Chesterfield Gorge Trail in Chesterfield, Massachusetts. A moderate 2.5-mile out-and-back trail.…

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Doane Rock Trail at Cape Cod

📍 Eastham

Easy 📏 1.5 Loop

Explore Doane Rock Trail at Cape Cod in Eastham, Massachusetts. A easy 1.5-mile loop trail.…

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Granville State Forest Trail

📍 Granville

Moderate 📏 6.0 Loop

Explore Granville State Forest Trail in Granville, Massachusetts. A moderate 6.0-mile loop trail.…

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Great Island Trail

📍 Wellfleet

Moderate 📏 4.5 Out-and-Back

Explore Great Island Trail in Wellfleet, Massachusetts. A moderate 4.5-mile out-and-back trail.…

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Great Meadows National Wildlife Refuge Trail

📍 Concord

Easy 📏 4.0 Loop

Explore Great Meadows National Wildlife Refuge Trail in Concord, Massachusetts. A easy 4.0-mile loop trail.…

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Halibut Point State Park Trail

📍 Rockport

Easy 📏 1.5 Loop

Explore Halibut Point State Park Trail in Rockport, Massachusetts. A easy 1.5-mile loop trail.…

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Harold Parker State Forest Trail

📍 North Andover

Moderate 📏 7.0 Loop

Explore Harold Parker State Forest Trail in North Andover, Massachusetts. A moderate 7.0-mile loop trail.…

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Hawley Bog Trail

📍 Hawley

Easy 📏 2.0 Loop

Explore Hawley Bog Trail in Hawley, Massachusetts. A easy 2.0-mile loop trail.…

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Ipswich River Wildlife Sanctuary Trail

📍 Topsfield

Easy 📏 4.0 Loop

Explore Ipswich River Wildlife Sanctuary Trail in Topsfield, Massachusetts. A easy 4.0-mile loop trail.…

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Lowell-Dracut-Tyngsboro State Forest Trail

📍 Lowell

Moderate 📏 5.0 Loop

Explore Lowell-Dracut-Tyngsboro State Forest Trail in Lowell, Massachusetts. A moderate 5.0-mile loop trail.…

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Lynn Woods Reservation Trail

📍 Lynn

Moderate 📏 6.0 Loop

Explore Lynn Woods Reservation Trail in Lynn, Massachusetts. A moderate 6.0-mile loop trail.…

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Maudslay State Park Loop — Newburyport, Massachusetts

📍 Newburyport, MA

Easy 📏 6.0 miles Loop

Hidden deep in the woods of Massachusetts, Maudslay State Park Loop offers 6.0 miles of classic American forest hiking a…

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Maudslay State Park Trail

📍 Newburyport

Moderate 📏 8.0 Loop

Explore Maudslay State Park Trail in Newburyport, Massachusetts. A moderate 8.0-mile loop trail.…

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Middlesex Fells Skyline Trail

📍 Medford

Moderate 📏 7.0 Loop

Explore Middlesex Fells Skyline Trail in Medford, Massachusetts. A moderate 7.0-mile loop trail.…

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Minute Man National Historic Park Trail — Concord, Massachusetts

📍 Concord, MA

Easy 📏 5.0 miles Out-and-back

Not every great trail needs to climb a mountain. Minute Man National Historic Park Trail proves the point beautifully — …

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Mohawk Trail State Forest Trail

📍 Charlemont

Hard 📏 6.5 Loop

Explore Mohawk Trail State Forest Trail in Charlemont, Massachusetts. A hard 6.5-mile loop trail.…

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Monument Mountain Trail

📍 Great Barrington

Moderate 📏 2.5 Loop

Explore Monument Mountain Trail in Great Barrington, Massachusetts. A moderate 2.5-mile loop trail.…

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Moore State Park Trail

📍 Paxton

Moderate 📏 3.5 Loop

Explore Moore State Park Trail in Paxton, Massachusetts. A moderate 3.5-mile loop trail.…

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Mount Everett Trail

📍 Sheffield

Hard 📏 4.0 Out-and-Back

Explore Mount Everett Trail in Sheffield, Massachusetts. A hard 4.0-mile out-and-back trail.…

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Mount Greylock Summit Trail

📍 Adams

Hard 📏 7.5 Out-and-Back

Explore Mount Greylock Summit Trail in Adams, Massachusetts. A hard 7.5-mile out-and-back trail.…

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Mount Greylock via Appalachian Trail — Massachusetts

📍 Mount Greylock State Reservation, Adams, MA

Hard 📏 5.9 miles (one-way) / 2 miles (from road) Out-and-back

The highest point in Massachusetts, Mount Greylock rises above the Berkshires in a landscape of boreal forest, sweeping …

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Mount Holyoke Range Trail

📍 South Hadley

Moderate 📏 7.0 Loop

Explore Mount Holyoke Range Trail in South Hadley, Massachusetts. A moderate 7.0-mile loop trail.…

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Mount Tom State Reservation Loop — Northampton, Massachusetts

📍 Northampton, MA

Hard 📏 5.5 miles Loop

Mount Tom State Reservation Loop is one of Massachusetts's most rewarding hiking destinations, offering 5.5 miles of cha…

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Mount Tom State Reservation Trail

📍 Holyoke

Hard 📏 5.5 Loop

Explore Mount Tom State Reservation Trail in Holyoke, Massachusetts. A hard 5.5-mile loop trail.…

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Mount Watatic Trail

📍 Ashburnham

Moderate 📏 3.5 Out-and-Back

Explore Mount Watatic Trail in Ashburnham, Massachusetts. A moderate 3.5-mile out-and-back trail.…

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Myles Standish State Forest Trail

📍 Plymouth

Easy 📏 8.0 Loop

Explore Myles Standish State Forest Trail in Plymouth, Massachusetts. A easy 8.0-mile loop trail.…

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Nauset Marsh Trail

📍 Eastham

Easy 📏 3.5 Loop

Explore Nauset Marsh Trail in Eastham, Massachusetts. A easy 3.5-mile loop trail.…

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Northfield Mountain Trail

📍 Northfield

Moderate 📏 7.0 Loop

Explore Northfield Mountain Trail in Northfield, Massachusetts. A moderate 7.0-mile loop trail.…

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October Mountain State Forest Trail

📍 Lee

Hard 📏 10.0 Loop

Explore October Mountain State Forest Trail in Lee, Massachusetts. A hard 10.0-mile loop trail.…

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Peaked Mountain Trail

📍 Monson

Moderate 📏 2.5 Out-and-Back

Explore Peaked Mountain Trail in Monson, Massachusetts. A moderate 2.5-mile out-and-back trail.…

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Plum Island Trail

📍 Newburyport

Easy 📏 4.5 Loop

Explore Plum Island Trail in Newburyport, Massachusetts. A easy 4.5-mile loop trail.…

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Purgatory Chasm Trail

📍 Sutton

Moderate 📏 1.5 Loop

Explore Purgatory Chasm Trail in Sutton, Massachusetts. A moderate 1.5-mile loop trail.…

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Quabbin Reservoir Trail

📍 Belchertown

Moderate 📏 6.0 Loop

Explore Quabbin Reservoir Trail in Belchertown, Massachusetts. A moderate 6.0-mile loop trail.…

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Quabbin Reservoir Trail — Belchertown, Massachusetts

📍 Belchertown, MA

Moderate 📏 8.0 miles Loop

Hidden deep in the woods of Massachusetts, Quabbin Reservoir Trail offers 8.0 miles of classic American forest hiking al…

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Ravenswood Park Trail

📍 Gloucester

Moderate 📏 4.5 Loop

Explore Ravenswood Park Trail in Gloucester, Massachusetts. A moderate 4.5-mile loop trail.…

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Robinson State Park Trail

📍 Agawam

Moderate 📏 6.0 Loop

Explore Robinson State Park Trail in Agawam, Massachusetts. A moderate 6.0-mile loop trail.…

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Rocky Narrows Trail

📍 Sherborn

Moderate 📏 4.5 Loop

Explore Rocky Narrows Trail in Sherborn, Massachusetts. A moderate 4.5-mile loop trail.…

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Tyringham Cobble Trail

📍 Tyringham

Moderate 📏 2.0 Loop

Explore Tyringham Cobble Trail in Tyringham, Massachusetts. A moderate 2.0-mile loop trail.…

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Wachusett Mountain State Reservation Trail

📍 Princeton

Moderate 📏 4.0 Loop

Explore Wachusett Mountain State Reservation Trail in Princeton, Massachusetts. A moderate 4.0-mile loop trail.…

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Wachusett Mountain Summit Loop — Princeton, Massachusetts

📍 Princeton, MA

Moderate 📏 4.5 miles Loop

Wachusett Mountain Summit Loop is one of Massachusetts's most rewarding hiking destinations, offering 4.5 miles of chall…

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Walden Pond Trail

📍 Concord

Easy 📏 1.7 Loop

Explore Walden Pond Trail in Concord, Massachusetts. A easy 1.7-mile loop trail.…

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Wellfleet Bay Wildlife Sanctuary Trail

📍 South Wellfleet

Easy 📏 3.0 Loop

Explore Wellfleet Bay Wildlife Sanctuary Trail in South Wellfleet, Massachusetts. A easy 3.0-mile loop trail.…

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Willowdale State Forest Trail

📍 Ipswich

Moderate 📏 8.0 Loop

Explore Willowdale State Forest Trail in Ipswich, Massachusetts. A moderate 8.0-mile loop trail.…

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Harold Parker State Forest MTB — North Andover, Massachusetts

📍 North Andover, MA

Moderate 📏 12.0 miles Loop

Harold Parker State Forest MTB is one of Massachusetts's premier mountain biking destinations, serving up 12.0 miles of …

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Middlesex Fells Reservation MTB — Medford, Massachusetts

📍 Medford, MA

Hard 📏 10.0 miles Loop

Middlesex Fells Reservation MTB is one of Massachusetts's premier mountain biking destinations, serving up 10.0 miles of…

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