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 …

Last updated: September 18, 2025

4.9

(10)

852

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.

Navigate

Send to Phone

Save

Intermediate

4.0

(20)

824

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.

Navigate

Send to Phone

Save

Intermediate

Let us show you the way with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures in England and beyond.

5.0

(1)

136

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.

Navigate

Send to Phone

Save

Intermediate

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.

Navigate

Send to Phone

Save

Intermediate

runners

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.

Navigate

Send to Phone

Save

Intermediate

5.0

(2)

runners

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.

Navigate

Send to Phone

Save

Intermediate

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.

Navigate

Send to Phone

Save

Intermediate

runners

8. Mass Central Rail Trail — Worcester

8.99km

00:56

50m

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

Navigate

Send to Phone

Save

Intermediate

runners

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.

Navigate

Send to Phone

Save

Expert

runners

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.

Navigate

Send to Phone

Save

Intermediate

Get access to more routes and recommendations from other explorers.

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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

Mountain Peaks

Waterfalls

Huts

Caves

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures around London and beyond.

Join komoot Now

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

Explore more

Browse the best Running Trails & Routes in other regions.

California Illinois Colorado Hawaii Texas Florida New York Honolulu County Oregon Utah Virginia Maui County Arizona Pennsylvania Washington Maryland Maine Missouri New Jersey Georgia North Carolina South Carolina Nevada Alaska Tennessee Appalachian Mountains Ohio New Hampshire Michigan Kauaʻi County Connecticut Nebraska Kentucky Rhode Island Kansas Oklahoma Minnesota Wisconsin Hawaiʻi County New Mexico Indiana Oregon Islands Wilderness South Dakota Idaho Wyoming Iowa North Dakota San Francisco San Francisco Washington D.C District Of Columbia Vermont Delaware Arkansas West Virginia San Juan Municipio San Juan Louisiana Puerto Rico Monroe County Cata O Municipio Cataño Toa Baja Toa Baja Municipio Alabama Montana Guaynabo Municipio Guaynabo Carolina Carolina Municipio Bayamón Bayamón Municipio Loíza Loíza Municipio Mississippi Dorado Municipio Trujillo Alto Municipio Trujillo Alto Guam Aguada Municipio Aguada United States Virgin Islands Aguadilla Municipio Aguadilla Toa Alta Municipio Toa Alta Moca Moca Municipio Cabo Rojo Cabo Rojo Municipio Rincón Añasco Rincon Municipio Cidra Cidra Municipio Salinas Municipio Salinas Aibonito Municipio Aibonito Aasco Municipio Dorado Cayey Cayey Municipio Caguas Caguas Municipio Lajas Municipio Lajas Comer�O Municipio Comerío Aguas Buenas Aguas Buenas Municipio San Germán San Germán Municipio

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

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️