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United States
Vermont
Windham County

Jacksonville

Easy hikes and walks around Jacksonville

5.0

(6)

50

hikers

6

hikes

Exploring Jacksonville on foot is a delightful way to connect with nature. To help you make the most of your adventures, we’ve compiled the top easy hikes and walks around Jacksonville. Perfect for short hikes, kid-friendly excursions, and family-friendly outings, these routes offer something for everyone.

Last updated: June 30, 2026

1

hikers

#1.

Lake Raponda Trail

4.34km

01:13

100m

50m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

5.0

(5)

26

hikers

2.85km

00:56

130m

140m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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13

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

5.0

(1)

11

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

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

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Tips from the Community

Lisa
October 12, 2023, Hoot Toot & Whistle Trail

The Hoot Toot & Whistle Trail follows an old railbed, once owned by a railroad of the same name. You can follow it from the boat launch alongside the Deerfield River all the way into town, or vice versa.

1

0

Lisa
October 12, 2023, Molly Stark statue

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.

1

0

Lisa
October 12, 2023, Mount Olga

Mount Olga stands just 2,415 feet (737 m) tall, but still offers grand views over the surrounding landscape — especially if you climb the fire lookout tower at the summit.

1

0

Most popular routes around Jacksonville

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