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Closest Hiking Trails Near Boston, Massachusetts, United States

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Hiking Trail Difficulty: Easy - Intermediate - Strenuous
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1. Middlesex Fells Reservation (7.0 miles)

Nice woods near the city.

Medford, Massachusetts, United States

Difficulty:

Distance:

Elevation Gain:

Easy

6.9 miles

n/a

2. North South Trail (77.6 miles)

Runs from the Rhode Island beaches to the Massachusetts border paralleling the Rhode Island and Connecticut border.

Westerly, Rhode Island, United States

Difficulty:

Distance:

Elevation Gain:

Intermediate

77.0 miles

10 ft

3. South Portland Greenbelt Walkway (97.3 miles)

Pedestrian path that connects South Portland parks and neighborhoods from the Wainwright Recreation Complex to Bug Light Park and the Spring Point Shoreway

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

5.7 miles

n/a

4. Stroudwater Trail (97.4 miles)

This lovely wooded trail follows the winding banks of the Stroudwater River

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Intermediate

5.3 miles

n/a

5. Fore River Parkway Trail (97.6 miles)

The wide, paved trail offers lovely views of the Fore River

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

2.6 miles

n/a

6. Thompson's Point (97.7 miles)

This extension of the Fore River Trail is a fascinating juxtaposition between Portland 's past and present

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

0.6 miles

n/a

7. Fore River Trail (97.7 miles)

Interpretive signage along the trail describes the area's fragile ecosystem and the damage caused by the spill

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

2.0 miles

n/a

8. Capisic Brook Trail (98.1 miles)

Capisic Park is a city-owned 18-acre nature preserve that affords fine views of Capisic Pond, Portland 's largest freshwater pond

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

1.0 miles

n/a

9. Westbrook River Walk (98.1 miles)

An attractive bike and pedestrian path follows the bank of the Presumpscot River

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

1.2 miles

n/a

10. Fore River Sanctuary (98.3 miles)

This 85-acre preserve is the home of Jewell Falls, Portland 's only natural waterfall, as well as the site of the former Cumberland and Oxford Canal

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

2.0 miles

n/a

11. Spring Point Shoreway Trail (98.5 miles)

This refreshing trail is on two levels, one wheelchair, stroller and bike-friendly with the middle portion forming a loop

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

1.6 miles

n/a

12. Harborwalk Trail (98.9 miles)

The Harborwalk Trail follows paved trails and sidewalks from Portland's East End Beach around the harbor and across the Casco Bay Bridge to the South Portland Greenbelt Walkway and Bug Light Park

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

6.4 miles

n/a

13. Baxter Woods (99.0 miles)

Baxter Woods is a 30-acre nature preserve offering towering pines, river views and quiet, shaded trails suitable for foot and bike traffic

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

0.8 miles

n/a

14. Evergreen Cemetery (99.3 miles)

Established in 1855, Evergreen Cemetery 's 239 acres make it the largest cemetery in Maine

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

1.0 miles

n/a

15. Eastern Prom Trail (99.7 miles)

This waterfront trail built along an old rail corridor offers spectacular harbor and ocean views

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

2.1 miles

n/a

16. Peaks Island Loop (99.7 miles)

Peaks Island offers spectacular views of towns, and neighboring islandsCasco Bay, the Atlantic Ocean, coastal

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

4.0 miles

n/a

17. Back Cove Trail (99.8 miles)

One of the oldest and most popular of the trails in Portland

Portland, Maine, United States

Difficulty:

Distance:

Elevation Gain:

Easy

3.5 miles

n/a