The Best Hiking in Boston
Looking for the best hiking in Boston? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Boston. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top hiking spots in and near Boston
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Boston, Massachusetts
Public Garden Monument Walking Tour
1.18 mi / 43 ft gainPublic Garden Monument Walking Tour is a loop trail that takes you by the lake located near Boston, Massachusetts.Read more -
Boston, Massachusetts
Commonwealth Ave Monument Tour
2.17 mi / 20 ft gainCommonwealth Ave Monument Tour is an out-and-back trail where you may see beautiful wildflowers located near Boston, Massachusetts.Read more -
Boston, Massachusetts
Boston City View Bike Route
10.1 mi / 413 ft gainBoston City View Bike Route is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.Read more -
Boston, Massachusetts
Franklin Park
2.26 mi / 164 ft gainFranklin Park is a loop trail that takes you by the lake located near Dorchester, Massachusetts.Read more -
Boston, Massachusetts
Freedom Trail
4.72.9 mi / 121 ft gainPark along the trail and then hop on. The Freedom Trail allows you to not only see the most beautiful parts of Boston (which is an absolutely gorgeous city) but you can learn some history too! Head off the trail a bit to explore the Charles River, the waterfront near the aquarium and picturesque ...Read more -
Boston, Massachusetts
Charles River Short Bike Loop Trail
3.45 mi / 33 ft gainCharles River Short Bike Loop Trail is a loop trail that takes you by a river located near Cambridge, Massachusetts.Read more -
Boston, Massachusetts
Exploring Boston's North End
4.91 mi / 266 ft gainExploring Boston's North End is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.Read more -
Cambridge, Massachusetts
Charles River Reservation Full Bike Loop
28.2 mi / 745 ft gainCharles River Reservation Full Bike Loop is a loop trail where you may see beautiful wildflowers located near Cambridge, Massachusetts.Read more -
Boston, Massachusetts
Jamaica Pond
1.46 mi / 36 ft gainJamaica Pond is a loop trail that takes you past scenic surroundings located near Boston, Massachusetts.Read more -
Boston, Massachusetts
Boston Harbor and Castle Island
2.2 mi / 98 ft gainBoston Harbor and Castle Island is a loop trail where you may see beautiful wildflowers located near Boston, Massachusetts.Read more -
Boston, Massachusetts
Run the Arnold Arboretum Trail
5.02.6 mi / 150 ft gainPark in the lot off of Arborway to access the trail. This place is gorgeous year round. The winter offers a quiet solitude, fall boasts bright colors, spring is the most beautiful as the flowers start to burst and cherry blossoms take over, and summer is overwhelmingly green. There are dozens of ...Read more -
Cambridge, Massachusetts
Harvard Yard Tour
1.76 mi / 56 ft gainHarvard Yard Tour is a loop trail where you may see beautiful wildflowers located near Cambridge, Massachusetts.Read more -
Boston, Massachusetts
Chestnut Hill Reservoir Trail
1.6 mi / 69 ft gainChestnut Hill Reservoir Trail is a loop trail that takes you by the lake located near Chestnut Hill, Massachusetts.Read more -
Cambridge, Massachusetts
Mount Auburn Loop
1.42 mi / 128 ft gainMount Auburn Loop is a loop trail that takes you through a nice forest located near Cambridge, Massachusetts.Read more -
Cambridge, Massachusetts
Mount Auburn Cemetery Trail
3.15 mi / 279 ft gainMount Auburn Cemetery Trail is a loop trail where you may see beautiful wildflowers located near Watertown, Massachusetts.Read more -
Newton, Massachusetts
Hammond Pond and Webster West
2.57 mi / 292 ft gainHammond Pond and Webster West is a loop trail that takes you by the lake located near Chestnut Hill, Massachusetts.Read more