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
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.
4
riders
65.6km
02:47
550m
560m
This moderate 40.7-mile road cycling loop near Middlebury offers scenic New England views, charming villages, and challenging climbs.

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177
riders
119km
05:46
1,680m
1,680m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
86
riders
97.8km
04:41
1,270m
1,270m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
62
riders
94.6km
04:54
1,170m
1,170m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
34
riders
39.3km
01:45
390m
390m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
21
riders
79.2km
03:23
630m
630m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
26
riders
41.9km
01:54
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
19
riders
22.3km
00:57
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
15
riders
29.6km
01:11
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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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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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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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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A very beautiful area along farms
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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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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.


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