Cycling in Middlesex County is one of the most enjoyable ways to explore more of this part of Massachusetts. So you can find your perfect Middlesex County bike ride, we’ve reviewed our full collection of cycling routes in the region to deliver the best. Just click on each route to see a full breakdown of detailed information including elevation profiles and surface analyses, and browse real tips and photos uploaded by other members of the komoot community.

Last updated: October 14, 2025

4.6

(30)

352

riders

1. Waltham to the Longfellow Bridge loop via Charles River Greenway & Dr. Paul Dudley White Path — Boston

37.6km

02:16

70m

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

Navigate

Send to Phone

Save

Intermediate

4.8

(19)

351

riders

2. Minuteman Bikeway — Boston, Massachusetts

32.9km

01:52

120m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

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.

4.8

(17)

258

riders

3. Minuteman Bikeway & Reformatory Branch Rail Trail to Moore's Swamp Overlook

44.3km

02:51

130m

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

Navigate

Send to Phone

Save

Intermediate

4.8

(21)

141

riders

4. Everett to Lynn via Northern Strand Trail Loop — Middlesex County

36.2km

02:02

60m

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

Navigate

Send to Phone

Save

Intermediate

5.0

(8)

130

riders

5. Bruce Freeman Rail Trail: Lowell to Acton

36.4km

02:06

100m

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

Navigate

Send to Phone

Save

Intermediate

4.4

(10)

riders

6. Walden Pond & Cambridge Reservoir loop via Minuteman Bikeway — Arlington

46.6km

02:58

270m

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

Navigate

Send to Phone

Save

Intermediate

5.0

(5)

riders

7. Lexington & Concord loop from Waltham via Battle Road Trail & Minuteman Bikeway — Greater Boston Area

54.7km

03:31

280m

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

Navigate

Send to Phone

Save

Intermediate

riders

8. Middlesex Fells Bicycle Loop

9.94km

00:57

110m

100m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Easy

5.0

(5)

riders

9. Bruce Freeman Rail Trail - Reformatory Branch Trail Loop

44.7km

02:59

220m

Intermediate bike ride. 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 Middlesex County

Bay Circuit Trail and Greenway — Walking the Emerald Necklace

Hiking Collection by

Eric

Bay Circuit Trail & Greenway — Pedal Boston’s Greenbelt

Mountain Biking Collection by

Frank

Most popular routes in Middlesex County

Road Cycling Routes in Middlesex County

Hiking in Middlesex County

Running Trails in Middlesex County

MTB Trails in Middlesex County

Easy hikes in Middlesex County

Gravel biking in Middlesex County

Waterfall hikes in Middlesex County

Most popular attractions in Middlesex County

Places to see

Lakes

Natural Monuments

Mountain Peaks

Bike Parks

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 Cycling routes throughout Middlesex County below and find the perfect route in your destination.

Hopkinton State Park Great Meadows National Wildlife Refuge Cochituate Hanscom Afb J. Harry Rich State Forest Pinehurst Farnsworth Wildlife Refuge Callahan State Park Malden Cambridge Assabet National Wildlife Refuge Newton Lowell Dracut Tyngsborough State Forest Marlborough-Sudbury State Forest Governor Thomas Dudley State Park Reading Wakefield Ashland State Park Whitehall State Park Ayer Main Street Wildlife Refuge Warren H Manning State Park Everett English Wildlife Refuge East Pepperell Framingham Hopkinton Billerica State Forest West Concord Loker Conservation And Recreation Area Marlborough Belmont Melrose Lowell Heritage State Park Lexington Hudson Watertown Waltham Wilmington Winchester Woburn Arlington Lowell Townsend Stoneham Pepperell Burlington Carlisle State Forest Littleton Common Somerville Maynard Medford Groton Shirley Lost Lake Recreation Area Great Brook Farm State Park Weston Pond Recreation Area Cochituate State Park Townsend State Forest

Explore more

Browse the best Cycling routes in other regions.

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

The best cycling routes in Middlesex County

1. Waltham to the Longfellow Bridge loop via Charles River Greenway & Dr. Paul Dudley White Path — Boston

2. Minuteman Bikeway — Boston, Massachusetts

3. Minuteman Bikeway & Reformatory Branch Rail Trail to Moore's Swamp Overlook

4. Everett to Lynn via Northern Strand Trail Loop — Middlesex County

5. Bruce Freeman Rail Trail: Lowell to Acton

6. Walden Pond & Cambridge Reservoir loop via Minuteman Bikeway — Arlington

7. Lexington & Concord loop from Waltham via Battle Road Trail & Minuteman Bikeway — Greater Boston Area

8. Middlesex Fells Bicycle Loop

9. Bruce Freeman Rail Trail - Reformatory Branch Trail Loop

Other adventures in Middlesex County

Most popular routes in Middlesex County

Most popular attractions in Middlesex County

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 ⛰️