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J F M A M J J A S O N D

187 mi 300 km of trail 15 Recommended Routes

Easy Trails 111 Trails Intermediate Trails 68 Trails Hard Trails 8 Trails
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Recommended Routes in Boston Metro - 15

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Favorite short-coated brown dog
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 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 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 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 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 Hiking up Whipple Hill. Photo provided by the Town of Lexington, Conservation Division.
Intermediate

Whipple Hill Loop

2.4 mi 3.8 km 214' Up 65.25 m Up 213' Down 65.06 m Down

Arlington, MA
Favorite 20140406-DSC_0009
Intermediate

Buck Hill Loop

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

Milton, 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

Virginia Woods Loop

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

Melrose, MA

Trails in Boston Metro - 172

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

2.2 mi 3.6 km #1Peabody Loop
Intermediate
Dover, MA
Intermediate
Dover, MA
0.5 mi 0.8 km #2Needham Reservoir Trail
Easy
Needham, MA
Easy
Needham, MA
1.5 mi 2.5 km #3Healthy Heart Trail
Easy
Melrose, MA
Easy
Melrose, MA
1.7 mi 2.8 km #4Page & Sadie Trail
Intermediate
Westwood, MA
Intermediate
Westwood, MA
1.8 mi 2.9 km #5Acton Path
Easy/Intermediate
Canton, MA
Easy/Intermediate
Canton, MA
1.1 mi 1.8 km #6Loop Trail
Easy
Canton, MA
Easy
Canton, 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 10 
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
5.9 mi 9.5 km #11Reservoir Trail
Easy/Intermediate
Winchester, MA
Easy/Intermediate
Winchester, MA
5.8 mi 9.3 km #12Western Greenway
Easy/Intermediate
Belmont, MA
Easy/Intermediate
Belmont, MA
4.8 mi 7.8 km #13Cross Fells Trail
Intermediate
Medford, MA
Intermediate
Medford, MA
1.1 mi 1.7 km #14Coon Hollow Path
Difficult
Milton, MA
Difficult
Milton, MA
0.2 mi 0.4 km #15Schoolmaster Hill Trail
Easy
Jamaica Plain, MA
Easy
Jamaica Plain, MA
1.0 mi 1.6 km #16Jejunum
Difficult
Burlington, MA
Difficult
Burlington, MA
1.0 mi 1.6 km #17Split Rock Trail
Intermediate
Westwood, MA
Intermediate
Westwood, MA
0.7 mi 1.1 km #18Strawberry Hill Alternate Trail
Difficult
Dover, MA
Difficult
Dover, MA
0.5 mi 0.8 km #19Strawberry Hill Shortcut
Intermediate
Dover, MA
Intermediate
Dover, MA
0.7 mi 1.2 km #20Zigzag Lollipop
Intermediate
Dover, MA
Intermediate
Dover, MA

Photos of Boston Metro - 126

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