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Favorite Middlesex Fells, Medford, United States
Intermediate/Difficult Intermediate/Difficult

Skyline Trail

7.5 mi 12.1 km 846' Up 257.71 m Up 863' Down 262.89 m Down

Winchester, MA
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Favorite The Great Blue Hill Observation Tower
Difficult Difficult

Blue Hills Loop

4.1 mi 6.5 km 1,171' Up 356.87 m Up 1,165' Down 355.22 m Down

Dedham, MA
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Favorite The Ocean Loop Trail offers purely phenomenal views.
Easy Easy

Sachuest Point Figure-Eight

2.7 mi 4.4 km 58' Up 17.6 m Up 57' Down 17.43 m Down

Newport, RI
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Favorite A beautiful look at the fall leaves that are just beginning to turn color.
Intermediate Intermediate

Ponkapoag Pond Loop

4.4 mi 7.0 km 229' Up 69.67 m Up 228' Down 69.44 m Down

Milton, MA
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Favorite Thoreau's Cabin.
Easy Easy

Walden Pond

1.8 mi 2.9 km 44' Up 13.43 m Up 43' Down 13.18 m Down

Concord, MA
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Favorite Tower Hill Pond Loop Trail
Easy Easy

Tower Hill Pond Loop Trail

4.0 mi 6.5 km 101' Up 30.72 m Up 101' Down 30.68 m Down

Auburn, NH
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Favorite Experiencing the Old King's Highway seems to bring you back in time.
Intermediate/Difficult Intermediate/Difficult

Pamet Loop

5.4 mi 8.7 km 239' Up 72.87 m Up 239' Down 72.94 m Down

Truro, MA
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Favorite An autumn view of Boston from the Fells
Intermediate Intermediate

Wright's Tower Out-and-Back

0.9 mi 1.5 km 138' Up 42 m Up 137' Down 41.88 m Down

Medford, MA
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Favorite No Photos
Intermediate Intermediate

Blackall Family and Ballou Farm Preserve

3.8 mi 6.2 km 323' Up 98.6 m Up 325' Down 98.97 m Down

Cumberl…, RI
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Favorite Greeting Tree at trailhead.
Intermediate Intermediate

Vernal Pool Loop

1.8 mi 2.9 km 99' Up 30.28 m Up 99' Down 30.03 m Down

Sharon, MA
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Favorite Taken last year at Borderland State Park.
Intermediate Intermediate

Borderland State Park Loop

4.6 mi 7.4 km 234' Up 71.21 m Up 227' Down 69.31 m Down

Easton, MA
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Favorite Almost to Dungeon Rock
Intermediate Intermediate

Lynn Woods Loop

7.0 mi 11.2 km 543' Up 165.53 m Up 541' Down 164.95 m Down

South P…, MA
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Favorite Start of the Pine Trail
Intermediate Intermediate

Pine Tree Trail

3.7 mi 6.0 km 216' Up 65.94 m Up 216' Down 65.98 m Down

Pocasset, MA
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Favorite Average high tide marker for 2025 and the intersection of Goose Pond Trail and Try Island Trail.
Easy/Intermediate Easy/Intermediate

Wellfleet Audobon Loop

1.7 mi 2.8 km 57' Up 17.47 m Up 58' Down 17.56 m Down

North E…, MA
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Favorite The great trail running fun does not end with winter. Bring the snowshoes or microspikes.
Intermediate Intermediate

Perimeter Trail

4.7 mi 7.6 km 364' Up 110.99 m Up 362' Down 110.43 m Down

Stratha…, NH
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Favorite The Girl in the Surf
Intermediate Intermediate

Crane Beach Loop

3.9 mi 6.2 km 119' Up 36.35 m Up 119' Down 36.34 m Down

Ipswich, MA
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Favorite Middlesex Fells Reservation
Intermediate/Difficult Intermediate/Difficult

Rock Circuit Loop

4.6 mi 7.4 km 619' Up 188.64 m Up 619' Down 188.75 m Down

Medford, MA
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Favorite The vines on the tall trees make this area look very rainforest like.
Intermediate Intermediate

Beaver Brook Loop

2.6 mi 4.2 km 256' Up 78.08 m Up 260' Down 79.11 m Down

Belmont, MA
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Favorite Nice view of the water
Intermediate Intermediate

Musquash Loop

6.5 mi 10.4 km 318' Up 96.84 m Up 318' Down 96.79 m Down

Londond…, NH
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Favorite Damde Meadow tidal marsh at low tide
Easy/Intermediate Easy/Intermediate

World's End Loop

3.1 mi 5.0 km 181' Up 55.03 m Up 180' Down 55.01 m Down

Hingham, MA
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Favorite View towards Boston.
Easy/Intermediate Easy/Intermediate

Ward Reservation

3.5 mi 5.7 km 227' Up 69.24 m Up 225' Down 68.67 m Down

Andover, MA
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Favorite 20140406-DSC_0009
Intermediate/Difficult Intermediate/Difficult

Buck Hill Loop

5.3 mi 8.6 km 583' Up 177.75 m Up 583' Down 177.79 m Down

Milton, MA
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Favorite Stone Bridge Waterfall" by Eric Kilby (https://www.flickr.com/photos/ekilby/9113874150/in/photolist-eTmZgd-eTmYqL-eTmZU1-eTazyP/), Flickr licensed under CC BY-SA 2.0 (https://creativecommons.org/licenses/by-sa/2.0/).
Easy/Intermediate Easy/Intermediate

Virginia Woods Loop

0.9 mi 1.5 km 117' Up 35.64 m Up 118' Down 35.9 m Down

Melrose, MA
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Favorite 99 Steps
Intermediate Intermediate

Franklin Park Loop

2.9 mi 4.7 km 128' Up 38.98 m Up 125' Down 38.05 m Down

Jamaica…, MA
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Favorite Across the Merrimack River
Easy/Intermediate Easy/Intermediate

Bedford Heritage Trail

1.8 mi 2.9 km 47' Up 14.31 m Up 47' Down 14.33 m Down

Bedford, NH
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Favorite Beebe lake
Intermediate/Difficult Intermediate/Difficult

Eight Mile Tour

8.4 mi 13.6 km 756' Up 230.46 m Up 756' Down 230.35 m Down

Southbo…, MA
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Favorite View towards Boston.
Intermediate Intermediate

Boston Hill Loop

3.1 mi 5.1 km 428' Up 130.56 m Up 425' Down 129.42 m Down

Andover, MA
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Favorite Muddy, rocky, and technical, this section will test your foot placement!
Intermediate Intermediate

Outer Loop

2.9 mi 4.6 km 104' Up 31.64 m Up 104' Down 31.71 m Down

Swansea, MA
Explore in 3D
Favorite Large maple at Habitat Education Center and Wildlife Sanctuary.
Easy Easy

Highland Farm Loop

1.4 mi 2.3 km 39' Up 12 m Up 39' Down 12.01 m Down

Belmont, MA
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Favorite There are several boardwalks along the East side of short park loop
Easy Easy

Livingstong Park Loop

1.1 mi 1.8 km 42' Up 12.79 m Up 42' Down 12.92 m Down

Manchester, NH
Explore in 3D
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