9
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3
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Touring cycling routes around Chimney Hill are situated within the Green Mountains of Southern Vermont, offering access to extensive natural landscapes. The region features a wooded environment with varied terrain, including the southeastern slopes of Haystack Mountain. Cyclists can expect routes that traverse mountains, historic covered bridges, and fertile farming valleys, with elevation changes characteristic of a mountainous area. The area is also known for its clear lakes and rivers, providing scenic backdrops for rides.
Last updated: June 24, 2026
2
riders
67.7km
05:37
960m
950m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3
riders
26.8km
01:38
240m
240m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
35.0km
02:28
630m
630m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
2
riders
27.0km
01:49
410m
410m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Chimney Hill
A small, pretty lake just off the Valley Trail — your reward for a little bit or a little of walking, depending on where you started the trail.
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This statue honors Elizabeth Page "Molly" Stark, the wife of General John Stark, who won the Battle of Bennington during the American Revolutionary War. Molly herself is said to have been a staunch, fierce, and devoted woman during the difficult times of war.
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Nice view of the reservoir, plenty of places to sit. Decent, but exposed stealth camping option for a three-day tour of the Roundabout Battlebro route in a pinch.
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Ample dispersed pull off campsites along this fast, paved gravel descent. Not much thru traffic, but expect competition from car campers for the choicest sites.
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There are 5 touring cycling routes available around Chimney Hill, offering a range of experiences from moderate to difficult.
The terrain around Chimney Hill is characteristic of the Green Mountains of Southern Vermont. You can expect a wooded environment with varied landscapes, including routes that traverse mountains, fertile farming valleys, and scenic lake views. Many routes feature notable elevation changes, making them suitable for cyclists looking for a challenge.
While the routes around Chimney Hill are generally categorized as moderate to difficult due to the mountainous terrain, the Molly Stark statue loop from Mirror Lake is one of the more accessible moderate options, covering 16.7 miles with a manageable elevation gain of 242 meters.
The region is rich in natural beauty. You can enjoy views of Mirror Lake on routes like the Molly Stark statue loop from Mirror Lake. The broader area also features lush green mountains, clear lakes, and rivers. For specific points of interest, consider visiting the West Side of Adams Reservoir or exploring trails near Mount Olga and Haystack Mountain.
The late summer and fall foliage seasons are particularly beautiful for cycling in Southern Vermont. The lush green mountains transform into vibrant colors, offering stunning backdrops for your rides. However, the region is generally attractive for cycling throughout the warmer months.
Yes, all the touring cycling routes listed for Chimney Hill are circular loops. For example, you can try the challenging Mirror Lake – Molly Stark statue loop from Drop Off Area or the moderate Molly Stark statue loop from Snow Lake.
For experienced touring cyclists seeking a challenge, the Deerfield River – Molly Stark statue loop from Mt Mills West Picnic Area is a difficult 42.1-mile route with a significant elevation gain of over 950 meters. Another difficult option is the Mirror Lake – Molly Stark statue loop from Drop Off Area, which covers nearly 35 miles with over 630 meters of ascent.
While the listed touring routes are moderate to difficult, the broader Chimney Hill community offers various amenities. The nearby historic downtown Wilmington provides shops and restaurants. For more relaxed cycling, the region has other trails like the 'Valley Trail' which is suitable for mountain biking, e-biking, and gravel cycling, potentially offering easier sections for families.
Specific parking details vary by route start point. For instance, the Deerfield River – Molly Stark statue loop starts from the Mt Mills West Picnic Area, which typically offers parking facilities. Always check the individual route details on komoot for precise starting locations and parking information.
Cycling through the Green Mountain National Forest and wooded areas, you might encounter various wildlife common to Vermont, including deer, wild turkeys, and a variety of bird species. Keep an eye out, especially during quieter times of day, and always maintain a respectful distance.
The historic downtown Wilmington, just minutes from Chimney Hill, offers a selection of shops and restaurants. Additionally, the Chimney Hill community itself provides amenities like a clubhouse. For a wider range of options, the charming town of Middlebury, though a bit further, is known as a convenient base with amenities for cyclists.
The duration varies significantly by route and individual pace. For example, the moderate Mirror Lake – Molly Stark statue loop from Chimney Hill typically takes around 1 hour 50 minutes, while the difficult Deerfield River – Molly Stark statue loop can take over 5 hours 30 minutes.


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