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Road cycling routes
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Addison County

The best road cycling routes in Addison County

5.0

(4)

688

riders

52

rides

Road cycling routes in Addison County traverse a diverse landscape, situated between the Green Mountains to the east and Lake Champlain to the west. The region features a mix of challenging mountain climbs, such as the Middlebury Gap, and gentler routes through rolling farmland and along waterways. Cyclists can experience varied terrain, from paved roads to hard-packed dirt roads, offering views of mountains, fields, and the expansive Lake Champlain. This geographical position provides a range of elevation changes and scenic…

Last updated: April 24, 2026

10

riders

#1.

Chimney Point loop

54.5km

02:22

490m

490m

Cycle the moderate 33.9-mile Chimney Point loop, enjoying scenic views of Lake Champlain, the Adirondacks, and historic sites.

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Moderate

4

riders

This moderate 40.7-mile road cycling loop near Middlebury offers scenic New England views, charming villages, and challenging climbs.

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

Hard

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

Hard

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

Hard

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

Moderate

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

Moderate

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

Moderate

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

Easy

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

Easy
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Popular around Addison County

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Tips from the Community

Zachary
June 25, 2025, Chimney Point & State Historic Site

The site chronicles millennia of local history, from indigenous cultures to the French-Indian War and early America. They have a lot of interesting artefacts, but the hours can be odd so it's best to check the website before your ride if you are planning to stop by. The views of Lake Champlain, the bridge, and Fort St. Frederic across the water make this a pretty remarkable spot to visit.

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Zachary
June 25, 2025, Forest Dale

Forest Dale is a small community with a church, post office, and historic early-1800s ironworks, the ruins of which can be found on the northeast side of town. The Junction Store & Deli is open 7am-7pm most days if you want to grab a bite before continuing on your ride.

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Jamie S.
June 25, 2025, Main Street

The historic main street of Middlebury offers a quintessential small New England town experience. Unique local shops, art galleries, and restaurants in historic brick buildings line the street. Don't miss the opportunity to admire the beautiful white-steepled church and the picturesque town green.

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Middlebury Falls is a unique 20 foot waterfall on Otter Creek right in the center of this picturesque New England town. You get great views of the falls from this spot on a bridge on Main Street. You can also see the ruins of the old Powder House to the lefthand side of the falls. While they are beautiful all year round, Middlebury Falls are particularly interesting in the winter when they partially freeze over.

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Nice little area for break/rest by the river.

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A small town

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A very beautiful area along farms

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5

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Extremely hilly, sounds of nature, lot's to see & experience. Downhills are well worth the climbs. You definitely need to have some rides/climbing in your season. Update 7/26/25 Still crazy hilly & and punchy. However, the downhill runs are amazing..😉

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Frequently Asked Questions

How many road cycling routes are available in Addison County?

Addison County offers a wide selection of road cycling routes, with over 50 options available. These routes cater to various skill levels, ranging from easy rides to challenging mountain climbs.

Are there easy road cycling routes suitable for beginners or families in Addison County?

Yes, Addison County features 12 easy road cycling routes, perfect for beginners or those seeking a relaxed ride. These routes often traverse rolling farmland and offer continuous panoramas along Lake Champlain. A great option is the Leicester loop from Branbury State Park, which is an easy 13.9-mile (22.3 km) ride.

Where can I find challenging road cycling routes with significant climbs in Addison County?

For experienced cyclists seeking a challenge, Addison County boasts 6 difficult routes with substantial elevation gains. The region is known for its demanding mountain passes like the Middlebury Gap and the eastern side of Lincoln Gap, which features a 24% grade. Consider the Appalachian Gap – Middlebury Gap loop from Middlebury, a 72.9-mile (117.4 km) route with over 1600 meters of ascent, or the Middlebury Falls – Middlebury Gap loop from Middlebury for another demanding option.

What kind of terrain can I expect on road cycling routes in Addison County?

Road cycling in Addison County offers diverse terrain. You'll find routes along the tranquil shores of Lake Champlain, through rolling farmland, and into the challenging Green Mountains. Many routes combine paved roads with hard-packed dirt roads, providing a varied experience and stunning scenic backdrops.

What natural features or landmarks can I see along the road cycling routes?

Addison County's routes are rich with natural beauty and landmarks. You can cycle past the dramatic Middlebury Gap, witness the urban Middlebury Falls, or cross the historic Pulp Mill Covered Bridge. Many routes also offer views of prominent peaks like Lincoln Peak and scenic viewpoints like Sunset Ledge lookout - Long Trail.

Are there any road cycling routes that are loops?

Yes, many road cycling routes in Addison County are designed as loops, allowing you to start and end in the same location. Examples include the popular Chimney Point loop, which offers scenic views along Lake Champlain, and the Forest Dale & Brandon loop, winding through rural landscapes.

What is the best time of year for road cycling in Addison County?

The best time for road cycling in Addison County is typically from late spring through early fall. Summer offers warm weather perfect for exploring, while the fall foliage season provides breathtaking vistas, especially with the Green Mountains and Lake Champlain as a backdrop. Be mindful of potential snow and ice during winter months, which can make some routes impassable.

What do other road cyclists enjoy most about road cycling in Addison County?

The komoot community highly rates road cycling in Addison County, with an average score of 5.0 stars from 4 reviews. Cyclists often praise the region's diverse landscapes, from the serene Lake Champlain shoreline to the challenging mountain passes, and the variety of routes available for all skill levels. Nearly 700 road cyclists have used komoot to explore the area.

Are there any routes that pass by waterfalls?

Yes, you can incorporate waterfalls into your road cycling adventure. The Middlebury Falls, a 20-foot waterfall on Otter Creek, is located right in the heart of Middlebury. Routes like the Middlebury Falls – Pulp Mill Covered Bridge loop from Middlebury will take you past this urban natural attraction.

Are there any routes that offer views of Lake Champlain?

Absolutely. Many routes in Addison County provide stunning views of Lake Champlain, especially those in the western part of the county. The Chimney Point loop is a prime example, offering continuous panoramas of the lake and surrounding fields and mountains.

Can I find routes that pass through charming towns or offer opportunities for stops?

Yes, several routes connect charming towns and offer opportunities for breaks. The Triangle Bike Loop (TBL), for instance, connects Middlebury, Vergennes, Bristol, and New Haven, passing through other smaller towns. These routes provide chances to enjoy local restaurants, cafes, and explore unique shops, particularly in Middlebury's historic downtown.

Are there any routes that feature covered bridges?

Yes, Addison County is home to historic covered bridges that can be part of your cycling route. The Pulp Mill Covered Bridge is a notable landmark. You can explore routes like the Huntington Falls – Pulp Mill Covered Bridge loop from Middlebury to include this picturesque feature.

Most popular routes in Addison County

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

Moosalamoo National Recreation AreaBreadloaf WildernessJoseph Battell WildernessEast MiddleburyLincoln WoodsBristol Cliffs WildernessVergennesBristolNew HavenSouth LincolnMiddleburyCamels Hump State ForestKingsland Bay State ParkLincolnWeybridge Cave State ParkButton Bay State Park

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