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Routes
Road cycling routes
United States
Vermont
Addison County
Middlebury

Chimney Point loop

Moderate

2.7

(22)

79

riders

Chimney Point loop

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:

Dead Creek Wildlife Management Area

Waypoints

A

Start point

Parking

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1

29.3 km

Chimney Point & State Historic Site

Highlight • Historical 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 …

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B

54.5 km

End point

Parking

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Way Types & Surfaces

Way Types

36.4 km

18.0 km

120 m

Surfaces

54.4 km

120 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (140 m)

Lowest point (30 m)

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Weather

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Today

Monday 1 June

19°C

6°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to complete this road cycling loop?

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.

What is the terrain like on this road cycling loop?

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.

What scenic highlights and landmarks can I expect along the way?

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.

Is this road cycling loop suitable for beginners?

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.

What is the best time of year to cycle this route?

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.

Where can I park to access this route?

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.

Are there any permits or fees required to cycle this route?

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.

Is this road cycling route dog-friendly?

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.

Are there amenities like cafes or bike rentals nearby?

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.

Does this route intersect with other trails?

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.

Are there any particularly challenging sections or alternative routes to consider?

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.

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Chimney Point loop

02:22h

54.5km

490m

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