Running in Massachusetts is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes in Massachusetts—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: October 7, 2025

4.9

(10)

868

runners

1. Charles River loop from Cambridge via Anderson Memorial Bridge & Charles River Esplanade — Boston, Massachusetts

13.9km

01:29

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

4.0

(21)

838

runners

2. Charles River Esplanade loop from Copley — Boston

7.39km

00:47

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0

(1)

141

runners

3. Fort Independence loop via Boston Harbor Walk

10.5km

01:05

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0

(2)

runners

4. Reservoir Loop — Middlesex Fells Reservation

9.59km

01:32

80m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5. Charles River Reservation loop from Alston

8.57km

00:54

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0

(2)

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6. Boston's Freedom Trail — Boston Common

9.06km

00:57

50m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0

(1)

runners

7. Newton & Chestnut Hill loop — Newton

12.8km

01:20

100m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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8. Mass Central Rail Trail — Worcester

8.99km

00:56

50m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9. Blue Hills Skyline Trail — Blue Hills Reservation

24.1km

03:14

680m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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10. Walden Pond & Wright Woods Loop – Walden Pond State Reservation

8.70km

00:59

60m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Other adventures in Massachusetts

East Coast Greenway — An unforgettable ride along the Atlantic Seaboard

Cycling Collection by

Patrick

The Long Trail — America’s oldest long-distance path

Hiking Collection by

LunchboxLarry (CC BY 2.0)

Bay Circuit Trail and Greenway — Walking the Emerald Necklace

Hiking Collection by

Eric

Midstate Trail — 92 miles through the heart of Massachusetts

Hiking Collection by

Peti

The Robert Frost Trail — A Trek Through Frost’s Western Massachusetts

Hiking Collection by

chris.rycroft (CC BY 2.0)

Bay Circuit Trail & Greenway — Pedal Boston’s Greenbelt

Mountain Biking Collection by

Frank

North-South Trail — The Smallest State's Longest Walk

Hiking Collection by

John Phelan (CC BY-SA 3.0)

On the trail of the Pilgrim Fathers – road trip along the Atlantic coast

Hiking Collection

Most popular routes in Massachusetts

Road Cycling Routes in Massachusetts

Cycling in Massachusetts

Hiking in Massachusetts

Easy hikes in Massachusetts

MTB Trails in Massachusetts

Gravel biking in Massachusetts

Waterfall hikes in Massachusetts

Most popular attractions in Massachusetts

Places to see

Lakes

Natural Monuments

Mountain Peaks

Bike Parks

Waterfalls

Huts

Caves

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Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Massachusetts below and find the perfect route in your destination.

Plymouth County Bristol County Franklin County Dukes County Nantucket County Hampshire County Suffolk County Barnstable County Worcester County Hampden County Berkshire County Middlesex County Essex County Norfolk County

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The best running trails in Massachusetts

1. Charles River loop from Cambridge via Anderson Memorial Bridge & Charles River Esplanade — Boston, Massachusetts

2. Charles River Esplanade loop from Copley — Boston

3. Fort Independence loop via Boston Harbor Walk

4. Reservoir Loop — Middlesex Fells Reservation

5. Charles River Reservation loop from Alston

6. Boston's Freedom Trail — Boston Common

7. Newton & Chestnut Hill loop — Newton

8. Mass Central Rail Trail — Worcester

9. Blue Hills Skyline Trail — Blue Hills Reservation

10. Walden Pond & Wright Woods Loop – Walden Pond State Reservation

Other adventures in Massachusetts

Most popular routes in Massachusetts

Most popular attractions in Massachusetts

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