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Routes
Hiking trails & Routes
United States
Vermont
Washington County

Tootsie Roll, Leonard's Loop, Amenta's Way, and Flying Squirrel Trail

Routes
Hiking trails & Routes
United States
Vermont
Washington County

Tootsie Roll, Leonard's Loop, Amenta's Way, and Flying Squirrel Trail

Moderate

4.8

(5627)

11,392

hikers

Tootsie Roll, Leonard's Loop, Amenta's Way, and Flying Squirrel Trail

02:52

10.3km

190m

Hiking

Hike a moderate 6.4-mile loop through Green Mountain National Forest, featuring scenic views and varied terrain near Blueberry Lake.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Waypoints

A

Start point

Parking

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4.40 km

Viewpoint

Viewpoint

B

10.3 km

End point

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Way Types & Surfaces

Way Types

10.3 km

< 100 m

Surfaces

7.75 km

2.54 km

< 100 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 (550 m)

Lowest point (460 m)

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Weather

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Sunday 31 May

16°C

4°C

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access this trail?

Parking for the route, which includes sections of Tootsie Roll, Leonard's Loop, and Flying Squirrel trails, is typically available near the Blueberry Lake network in Warren, Vermont. This area serves as a common access point for many trails in the Green Mountain National Forest.

Is this route suitable for beginners or families with children?

Yes, sections of this route, particularly the Tootsie Roll and Leonard's Loop trails in Warren, Vermont, are rated as 'Green' (easy) difficulty with gentle grades and flowy lines, making them family-friendly. The Tootsie Roll trail, for example, has 'rolly' sections with easy technical features, and Leonard's Loop offers options for easier ascents. However, always consider the full 10.3 km distance and 188 meters of elevation gain for the entire composite route.

Are dogs allowed on the trail?

Yes, dogs are generally allowed on a leash on the Tootsie Roll, Leonard's Loop, and Flying Squirrel trails within the Green Mountain National Forest. Always ensure your dog is under control and follow Leave No Trace principles.

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

The best time to hike this route is typically from late spring through fall. During these seasons, the trails are usually clear of snow and ice, offering pleasant conditions for hiking. Fall foliage in the Green Mountain National Forest can be particularly stunning. Winter hiking is possible, but be prepared for snow and ice, as some sections are also used for Nordic skiing and snowshoeing.

Do I need a permit or is there an entrance fee for the Green Mountain National Forest?

Generally, there are no entrance fees to access the Green Mountain National Forest for day-use hiking. However, some specific recreation sites or trailheads might require a small fee or a pass for parking. It's always a good idea to check the USDA Forest Service website for the Green Mountain National Forest for the most current information on regulations and any potential fees.

What kind of terrain can I expect on this hike?

The terrain varies across the combined route. Sections like Tootsie Roll and Leonard's Loop in Vermont feature singletrack with gentle grades, sweeping turns, and flowy lines. Leonard's Loop includes a rocky section at the start and a brief climb. While generally manageable, some parts may have easy technical features, roots, or rocks, especially on the Flying Squirrel segments. The overall route has a moderate difficulty rating.

Are there any notable viewpoints or scenic spots along the way?

Yes, the Tootsie Roll trail in Warren, Vermont, offers 'sweetest trail views in the Mad River Valley,' especially when climbing through a field. Leonard's Loop may also offer an 'overlook' view near Blueberry Lake. The route winds through forested areas typical of the Green Mountain National Forest, providing a pleasant natural setting.

Does this route connect with other trails in the area?

Yes, this route is part of a larger network. It officially incorporates sections of Leonard's Loop, Amenta's Way, and Flying Squirrel trails. Additionally, it connects with Leonard's Loop Access and Suki's Alley, allowing for various extensions or alternative loops within the Blueberry Lake trail system and the Green Mountain National Forest.

What are the typical conditions for winter hiking or snowshoeing on these trails?

During winter, the trails in the Blueberry Lake network, including Tootsie Roll, Leonard's Loop, and Flying Squirrel, are often used for Nordic skiing and snowshoeing. Expect snow and potentially icy conditions. It's crucial to wear appropriate winter gear, including traction devices like microspikes or snowshoes, and to be aware of shared trail etiquette with skiers.

What should I bring for a hike on this route?

For this moderate 10.3 km hike, you should bring plenty of water, snacks, appropriate footwear (hiking shoes or boots), layers of clothing suitable for changing weather, a map or GPS device (like the komoot app), and sun protection. Given the forested environment, insect repellent can also be useful, especially during warmer months.

Is there a specific direction recommended for hiking this combined route?

While the overall route can be hiked in either direction, some local insights suggest that certain segments, like Leonard's Loop, can be ridden as a downhill segment after completing other trails like Flying Squirrel, or as an easier climb. For hiking, consider starting with the more challenging ascents early in your hike if you prefer to get them out of the way, or consult a detailed trail map for elevation profiles to choose your preferred direction.

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