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Routes
Road cycling routes
United States
Wisconsin
Forest County

Headwaters Wilderness

The best road cycling routes in Headwaters Wilderness

28

riders

5

rides

Road cycling routes in Headwaters Wilderness traverse a landscape characterized by forested lowlands, muskeg bogs, and hardwood ridges. The terrain is generally flat, with some routes featuring gentle elevation changes. This region, located in northeastern Wisconsin, includes areas with old-growth eastern white pine and eastern hemlock.

Best road cycling routes in Headwaters Wilderness

  • The most popular road cycling route is Burnt Rollways Reservoir 129 โ€“ Canary Lake loop from Denby Island, a 41.9 miles (67.5 km) trail that takesโ€ฆ

Last updated: April 26, 2026

4

riders

#1.

Wolf Lake loop from Hemlock Grove

49.6km

02:30

250m

250m

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Moderate

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

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

Easy

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

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Popular around Headwaters Wilderness

Hiking in Headwaters Wilderness

Tips from the Community

Zachary
November 10, 2023, Franklin Trailhead

From here you have access to the Franklin Nature Trail, boat launch, and waterside. If you start the Hidden Lakes loop from here, be sure to bring water since there are not many filtration sites. Going counter-clockwise leaves the best and most scenic lake hikes for last.

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Zachary
November 8, 2023, Anvil Lake Trailhead

The trails in the Anvil Lake system are mostly all wide, packed, and flat. The forest scenery is especially beautiful in autumn. There may be a fee to park at the trailhead.

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Frequently Asked Questions

Is road cycling permitted within the Headwaters Wilderness federal area?

No, the Headwaters Wilderness is a federally designated wilderness area where all mechanized equipment, including bicycles, is prohibited to preserve its primitive nature. However, the broader Chequamegon-Nicolet National Forest and surrounding regions offer road cycling opportunities on Forest Service roads and other paved routes, which is where the komoot routes in this guide are located.

Where is the Headwaters Wilderness region located?

The Headwaters Wilderness region is situated in northeastern Wisconsin, within the larger Chequamegon-Nicolet National Forest. It's known for its remote character and diverse natural landscapes.

What kind of terrain can I expect on road cycling routes in this region?

The road cycling routes in the Headwaters Wilderness region generally feature a flat to gently rolling terrain. You'll traverse forested lowlands, areas with muskeg bogs, and hardwood ridges. Some routes may have gentle elevation changes, but overall, it's not characterized by steep climbs.

What are the typical difficulty levels for road cycling routes here?

The routes in this guide cater to both easy and moderate ability levels. For example, the Franklin Trailhead loop from Four Ducks Lake is an easy route, while the Burnt Rollways Reservoir 129 โ€“ Canary Lake loop from Denby Island is considered moderate.

Are there any notable natural features or landmarks to see along the routes?

While the federal wilderness area itself contains features like Kimball Creek, Shelp Lake, and the Headwaters of the Pine River, the road cycling routes in the surrounding region offer views of forested areas and lakes. For instance, the Burnt Rollways Reservoir 129 โ€“ Canary Lake loop from Denby Island provides views of the reservoir.

How many road cycling routes are available in the Headwaters Wilderness region on komoot?

There are 6 road cycling routes detailed in this guide for the Headwaters Wilderness region, offering a variety of distances and experiences.

What is a popular moderate road cycling route in the area?

A popular moderate route is the Anvil Lake Trailhead loop from Denby Island. This path is 38.3 miles (61.6 km) long and takes approximately 2 hours 50 minutes to complete, featuring varied forest scenery.

Are there any easy road cycling routes suitable for beginners?

Yes, an easy option is the Franklin Trailhead loop from Four Ducks Lake. This route is 15.0 miles (24.2 km) long and typically takes about 1 hour 6 minutes, leading through pleasant forested areas.

What do other road cyclists say about the routes in this region?

More than 20 road cyclists have used komoot to explore the varied terrain of the Headwaters Wilderness region. They often appreciate the forested landscapes and the options available for different ability levels.

When is the best time of year for road cycling in the Headwaters Wilderness region?

While specific seasonal considerations for road cycling aren't detailed, the region experiences distinct seasons. Spring and fall typically offer pleasant temperatures and beautiful foliage, while summer can be warm. Winter cycling would likely be challenging due to snow and ice.

Are there any long-distance road cycling options?

Yes, for those looking for longer rides, routes like the Burnt Rollways Reservoir 129 โ€“ Canary Lake loop from Denby Island cover 41.9 miles (67.5 km), offering a substantial ride through the region.

What is the longest road cycling route available in this guide?

The longest route featured in this guide is the Burnt Rollways Reservoir 129 โ€“ Canary Lake loop from Denby Island, which spans 41.9 miles (67.5 km).

Most popular routes in Headwaters Wilderness

Hiking in Headwaters Wilderness

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