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Recommended Routes in Boston Metro - 14

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Favorite Middlesex Fells, Medford, United States
Intermediate/Difficult

Skyline Trail

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

Winchester, MA
Favorite The Great Blue Hill Observation Tower
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
Favorite A beautiful look at the fall leaves that are just beginning to turn color.
Intermediate

Ponkapoag Pond Loop

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

Milton, MA
Favorite An autumn view of Boston from the Fells
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
Favorite 20140406-DSC_0009
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
Favorite Middlesex Fells Reservation
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
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

Virginia Woods Loop

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

Melrose, MA
Favorite 99 Steps
Intermediate

Franklin Park Loop

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

Jamaica…, MA
Favorite Large maple at Habitat Education Center and Wildlife Sanctuary.
Easy

Highland Farm Loop

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

Belmont, MA

Boston Metro Hiking

  • 237 Miles 381 Kilometers of Trail
  • 14 Recommended Routes
  • 118 Easy Trails Easy Trails
  • 66 Intermediate Trails Intermediate Trails
  • 7 Difficult Trails Difficult Trails
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Areas Within Boston Metro

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Trails in Boston Metro - 177

Hiking Project is built by hikers like you. Add Your Trails

0.5 mi 0.8 km #1Needham Reservoir Trail
Easy
Needham, MA
Easy
Needham, MA
1.5 mi 2.5 km #2Healthy Heart Trail
Easy
Melrose, MA
Easy
Melrose, MA
1.7 mi 2.8 km #3Page & Sadie Trail
Intermediate
Westwood, MA
Intermediate
Westwood, MA
1.1 mi 1.8 km #4Loop Trail
Easy
Canton, MA
Easy
Canton, MA
1.8 mi 2.9 km #5Acton Path
Easy/Intermediate
Canton, MA
Easy/Intermediate
Canton, MA
0.4 mi 0.6 km #6Pond Loop
Easy
Arlington, MA
Easy
Arlington, MA
0.8 mi 1.3 km #7Rock Hill Extension
Intermediate
Westwood, MA
Intermediate
Westwood, MA
7.9 mi 12.7 km #8Skyline Trail
Difficult
Dedham, MA
Difficult
Dedham, MA 11 
1.1 mi 1.7 km #9Skyline Trail South
Difficult
Milton, MA
Difficult
Milton, MA
2.2 mi 3.6 km #10Storrow Pond Trail
Intermediate
Westwood, MA
Intermediate
Westwood, MA

Photos of Boston Metro - 131

Hiking Project is built by hikers like you. Add Your Photos

The view of the lake upon entering this trail.
Jun 13, 2020 near Saugus, MA
Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
Middlesex Fells, Medford, United States
Feb 19, 2020 near Winchester, MA
body of water near forest island
Feb 19, 2020 near Winchester, MA
short-coated brown dog
Feb 19, 2020 near Stoneham, MA
sunlight passing thru trees
Feb 19, 2020 near Winchester, MA
An autumn view of Boston from the Fells
Feb 19, 2020 near Medford, MA
snowy wood
Feb 19, 2020 near Winchester, MA