How many trails are near Winthrop?

We list 994 trails within 30 miles of Winthrop, Massachusetts. This page shows the 60 closest.

What is the longest trail near Winthrop?

Boston HarborWalk is the longest on this page at about 29 miles, 2.6 miles from Winthrop.

Are there dog-friendly trails near Winthrop?

Yes. Map data lists 11 trails on this page as open to dogs, including Boston HarborWalk, Mill Creek Riverwalk, Boston Boundless Trail Section 1. Most trails have no dog rule in our data yet, so check signs at the trailhead.

Trails near Winthrop, MA

994 trails within 30 miles of Winthrop, for hiking, biking, horseback riding and off-road riding. Tap a trail for its map, trailhead and directions.

Hiking trails (935) Walking trails (908) Bike trails (367) Mountain bike trails (282) Paved trails (155) Horse trails (63) ATV and UTV trails (3) Dirt bike trails (8) Off-road and 4x4 trails (4) Dog-friendly trails (26) Snowmobile trails (54) Cross-country ski trails (13) Wheelchair-accessible trails (16) Rail trails (23) Greenways (15)

Quick picks

Closest: Winthrop Greenway 0.6 mi, 0.8 mi away
Longest: Boston HarborWalk 29 mi, 2.6 mi away
Easy walk: Deer Island Loop Trail 2.7 mi, 1.6 mi away
Paved: Deer Island Loop Trail 2.7 mi, 1.6 mi away
Dog friendly: Boston HarborWalk 29 mi, 2.6 mi away

All nearby trails

Winthrop Greenway

0.8 mi away

0.6 mi long · Easy · Winthrop

Hiking Biking Paved Greenway

Deer Island Loop Trail

1.6 mi away

2.7 mi long · Easy · Winthrop

Hiking Biking Paved

Boston HarborWalk

2.6 mi away

29 mi long · Easy · Dogs on leash · Boston Seaport

Hiking Biking Paved Wheelchair accessible Dogs allowed

Mill Creek Riverwalk

2.7 mi away

0.7 mi long · Easy · Dogs on leash · Revere

Hiking Paved Dogs allowed

Chelsea Greenway

2.9 mi away

0.7 mi long · Easy · Chelsea

Hiking Biking Paved Greenway

East Boston Greenway

3.0 mi away

2.3 mi long · Easy · East Boston

Hiking Biking Paved Greenway

Harborwalk Charlestown

3.4 mi away

1.9 mi long · VA Boston Healthcare System, Brockton Campus

Hiking

Boston Boundless Trail Section 1

3.6 mi away

11 mi long · Easy · Dogs allowed · South Boston

Hiking Paved Dogs allowed

Washington-Rochambeau Revolutionary Route National Historic Trail

3.7 mi away

0.3 mi long · Easy · Boston

Hiking Paved

Freedom Trail

3.8 mi away

0.3 mi long · Boston National Historical Park

Hiking Wheelchair accessible

TO TOILET

3.9 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

TO CAMP

3.9 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

FIELD EDGE

3.9 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

NEWLY CLEARED

4.0 mi away

0.0 mi long · Boston Harbor Islands National Recreation Area

CAMPUS

4.1 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Rumney Marsh Restoration

4.1 mi away

1.7 mi long · Saugus

Hiking

FROM DOCK

4.1 mi away

0.2 mi long · Boston Harbor Islands National Recreation Area

BUILDINGS

4.2 mi away

0.1 mi long · Boston Harbor Islands National Recreation Area

BOARDWALK

4.2 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Broadway

4.4 mi away

0.5 mi long · Everett

Biking Mountain biking

South Bay Harbor Trail

4.5 mi away

0.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

BATTERY

4.5 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Northern Strand Community Trail

4.5 mi away

12 mi long · Easy · Saugus

Hiking Biking Paved

Lagoon Path

4.7 mi away

0.5 mi long · Easy · Dogs on leash · Friends of the Public Garden

Hiking Paved Wheelchair accessible Dogs allowed

STEPS

4.7 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

SW TRAIL

4.8 mi away

0.8 mi long · Boston Harbor Islands National Recreation Area

Everett Riverwalk

4.9 mi away

1.1 mi long · Malden

Hiking Biking Mountain biking

Dr. Paul Dudley White Path

5.1 mi away

17 mi long · Easy · Dogs on leash · Lower Allston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Somerville Community Path

5.2 mi away

3.0 mi long · Easy · Somerville

Hiking Biking Paved Wheelchair accessible

Jazz Along the Charles

5.2 mi away

0.4 mi long · Easy · Dogs allowed · Back Bay

Hiking Biking Paved Dogs allowed

Wellington Greenway

5.4 mi away

0.6 mi long · Easy · Ten Hills

Hiking Biking Paved Greenway

South Bay Harbor Trail

5.4 mi away

2.5 mi long · Easy · Dogs on leash · South Boston

Hiking Biking Paved Wheelchair accessible Dogs allowed

Walking City Trail Section 4

5.7 mi away

6.5 mi long · Easy · Dogs allowed · Friends of the Public Garden

Hiking Paved Dogs allowed

MAIN

6.0 mi away

1.4 mi long · Boston Harbor Islands National Recreation Area

Melnea Cass Bike Path

6.0 mi away

0.9 mi long · Easy · Roxbury Crossing

Biking Paved

W/STEPS

6.0 mi away

0.0 mi long · Easy · Boston Harbor Islands National Recreation Area

Paved

Cray Trail

6.1 mi away

0.6 mi long · Melrose

Hiking

Quincy RiverWalk

6.5 mi away

2.6 mi long · Easy · Ashmont

Hiking Biking Paved

Clippership Connector

6.6 mi away

0.5 mi long · Easy · Medford

Hiking Biking Paved

Nature Trail

6.6 mi away

0.1 mi long · Saugus Iron Works National Historic Site

Cross Fells Trail

6.7 mi away

4.6 mi long · Easy · Medford

Hiking Paved

Fells Path

6.7 mi away

0.4 mi long · Easy · Melrose

Hiking Paved

Saugus River Trail

6.9 mi away

1.1 mi long · Easy · Saugus

Hiking Biking Paved

Birch Pond Trail

6.9 mi away

1.4 mi long · Saugus

Hiking Biking Mountain biking

Rock Circuit Connector

7.0 mi away

0.6 mi long · Easy · Melrose

Hiking

White Rock Path

7.1 mi away

0.5 mi long · Easy · Melrose

Hiking Paved

Melrose Path

7.3 mi away

0.4 mi long · Easy · Melrose

Hiking

Rock Circuit Trail

7.4 mi away

4.1 mi long · Easy · Dogs on leash · Massachusetts Department of Conservation and Recreation

Hiking Dogs allowed

Concrete Walk to Basement

7.4 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Front Concrete Walkway

7.4 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Southwest Side and Rear Yard Concrete Walkway

7.4 mi away

0.0 mi long · Easy · John Fitzgerald Kennedy National Historic Site

Hiking Paved

Cornel Path

7.5 mi away

0.6 mi long · Easy · Saugus

Hiking Biking Mountain biking

Pine Grove Path

7.5 mi away

0.4 mi long · Easy · Melrose

Hiking Biking Mountain biking

Historic Trail

7.7 mi away

1.0 mi long · Easy · Melrose

Hiking

Virginia Wood Trail

7.7 mi away

0.4 mi long · Easy · Melrose

Hiking

Crystal Spring Trail

7.8 mi away

1.4 mi long · Easy · Melrose

Hiking

Ridge Trail

7.8 mi away

1.6 mi long · Moderate · Saugus

Hiking

Undercliff Path

7.8 mi away

0.5 mi long · Saugus

Hiking Biking Mountain biking

Ash Path

7.8 mi away

1.0 mi long · Saugus

Hiking Biking Mountain biking

Walking City Trail Section 3

7.9 mi away

5.7 mi long · Easy · Dogs allowed · Mission Hill

Hiking Paved Wheelchair accessible Dogs allowed

Add this trail map to your website

Free for parks, clubs, schools and local sites. Copy the code and paste it into your page.

<iframe src="https://trailsdirectory.com/embed/?p=/massachusetts/winthrop/" width="100%" height="420" style="border:0" loading="lazy" title="Trails near Winthrop"></iframe>
<p><a href="https://trailsdirectory.com/massachusetts/winthrop/">Trails near Winthrop</a> from TrailsDirectory.com</p>

Nearby cities

All trails in Massachusetts

Common questions

How many trails are near Winthrop?: We list 994 trails within 30 miles of Winthrop, Massachusetts. This page shows the 60 closest.
What is the longest trail near Winthrop?: Boston HarborWalk is the longest on this page at about 29 miles, 2.6 miles from Winthrop.
Are there dog-friendly trails near Winthrop?: Yes. Map data lists 11 trails on this page as open to dogs, including Boston HarborWalk, Mill Creek Riverwalk, Boston Boundless Trail Section 1. Most trails have no dog rule in our data yet, so check signs at the trailhead.