In this guide, we’ve reviewed our full collection of road biking routes in Addison County to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: October 9, 2025

riders

1. Chimney Point loop — Middlebury

54.5km

02:22

490m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Intermediate

riders

2. Forest Dale & Brandon loop — Middlebury

65.6km

02:47

550m

560m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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.

171

riders

3. Appalachian Gap – Middlebury Gap loop from Middlebury

117km

05:39

1,660m

Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Expert

riders

4. Rochester – Brandon Gap loop from Granville

94.6km

04:54

1,170m

Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Navigate

Send to Phone

Save

Expert

riders

5. Huntington Falls loop from Middlebury

39.3km

01:45

390m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Intermediate

riders

6. Middlebury Falls – Main Street loop from Middlebury

78.8km

03:21

620m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Intermediate

riders

7. Scenic Area Near Farms – Leicester loop from East Middlebury

41.4km

01:47

340m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Intermediate

riders

8. Leicester loop from Salisbury

22.3km

00:57

180m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Easy

riders

9. Main Street – Middlebury Gap loop from Middlebury

49.1km

02:21

680m

Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Intermediate

riders

10. Spade Farm Covered Bridge loop from Ferrisburgh

29.6km

01:11

140m

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Navigate

Send to Phone

Save

Easy

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.

Most popular routes in Addison County

Hiking in Addison County

Easy hikes in Addison County

Waterfall hikes in Addison County

Running Trails in Addison County

Cycling in Addison County

Gravel biking in Addison County

MTB Trails in Addison County

Most popular attractions in Addison County

Places to see

Natural Monuments

Mountain Peaks

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 Road cycling routes throughout Addison County below and find the perfect route in your destination.

New Haven Moosalamoo National Recreation Area Middlebury East Middlebury Lincoln Woods Kingsland Bay State Park Bristol Cliffs Wilderness Breadloaf Wilderness Joseph Battell Wilderness Bristol Camels Hump State Forest Vergennes Lincoln Weybridge Cave State Park Button Bay State Park

Explore more

Browse the best Road cycling routes in other regions.

Chittenden County Windsor County Washington County Grand Isle County Essex County Green Mountain And Finger Lakes National Forests Lamoille County Lake Champlain Bennington County Rutland County Franklin County Orange County Windham County Orleans County Caledonia County

The best road cycling routes in Addison County

1. Chimney Point loop — Middlebury

2. Forest Dale & Brandon loop — Middlebury

3. Appalachian Gap – Middlebury Gap loop from Middlebury

4. Rochester – Brandon Gap loop from Granville

5. Huntington Falls loop from Middlebury

6. Middlebury Falls – Main Street loop from Middlebury

7. Scenic Area Near Farms – Leicester loop from East Middlebury

8. Leicester loop from Salisbury

9. Main Street – Middlebury Gap loop from Middlebury

10. Spade Farm Covered Bridge loop from Ferrisburgh

Most popular routes in Addison County

Most popular attractions in Addison 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 ⛰️