2.7
(22)
79
riders
02:22
54.5km
490m
Road cycling
Cycle the moderate 33.9-mile Chimney Point loop, enjoying scenic views of Lake Champlain, the Adirondacks, and historic sites.
Last updated: February 26, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
Waypoints
Start point
Parking
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29.3 km
Highlight • Historical Site
Tip by
54.5 km
End point
Parking
Way Types & Surfaces
Way Types
36.4 km
18.0 km
120 m
Surfaces
54.4 km
120 m
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Elevation
Highest point (140 m)
Lowest point (30 m)
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Weather
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Monday 1 June
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Additional weather tips
Max wind speed: 14.0 km/h
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This route was planned by komoot.
This road cycling loop is approximately 54.5 kilometers (33.9 miles) long and typically takes around 2 hours and 22 minutes to complete, depending on your pace and stops.
The terrain is generally hilly with rolling climbs and winding descents. While mostly paved, some sections may include hard-packed dirt or gravel roads. You can expect varied landscapes, from bucolic roads to challenging mountain gaps.
You'll experience expansive views of Lake Champlain and the Adirondack Mountains. A key landmark is the Chimney Point & State Historic Site, which offers insights into the area's rich history. The route also features charming rural scenery, including farms, orchards, and forests.
The Chimney Point loop is rated as 'moderate' in difficulty. While some sections offer continuous panoramas and are less strenuous, routes connecting Middlebury and Chimney Point can vary significantly. Some incorporate challenging mountain climbs over gaps like Middlebury Gap, which require very good fitness. Beginners should research specific route variations to match their fitness level.
The region is known for its gorgeous landscapes, making it enjoyable throughout the warmer months. Fall foliage offers a particularly stunning experience. Consider seasonal weather conditions, as some mountain gaps can be more challenging in adverse weather.
Specific parking information for the Chimney Point loop is not detailed, but Middlebury and the Chimney Point Historic Site are common starting points. Look for public parking areas in Middlebury or near the historic site, keeping in mind local regulations.
No specific permits are required for cycling on public roads in Vermont. However, if you plan to visit the Chimney Point & State Historic Site, there may be an entrance fee for the site itself.
As a road cycling route, it primarily uses public roads. While dogs are generally allowed in public spaces, they should be kept on a leash and under control, especially in towns or near traffic. Always check specific rules for any parks or historic sites you might visit along the way.
Yes, Middlebury, Vermont, is a charming town that offers various amenities including cafes, pubs, and accommodation options. You may also find bike rental services in Middlebury, making it a convenient base for your ride.
Yes, sections of this route overlap with several other paths. You will find it intersects with parts of the Champlain Bikeway, USBR 7 (Vermont), and the North Country National Scenic Trail (VT), among others.
Routes in this area can include very challenging mountain gaps like Middlebury Gap, which requires very good fitness. Some routes in Addison County, such as those incorporating Lincoln Gap, feature the steepest paved mile in the U.S. with a 24% grade. If you prefer a less strenuous ride, look for routes described as 'easy' with continuous panoramas, as difficulty can vary significantly.