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Best Walking Trails & Routes in Chestertown

Q: Which is the best trail or route to walk in Chestertown?

According to Pacer users, the best trail to walk in Chestertown is Stewart Mountain Trail , which has a 4.0 star rating from 1 reviews. This walking route is 0.4 miles/0.7 km long.

Q: What is the longest trail or route in Chestertown?

According to Pacer’s walking routes data, the longest walking routes in Chestertown is Caroline Fish Memorial Trail . This walking route is 1.5 miles/2.4 km long.

Q: How many walking trails or routes are in Chestertown?

There are 8 walking trails or routes in Chestertown. These walking trails and routes have an average rating of 4.0 from users in the Pacer community.

Q: How do I find walking trails or routes near me in Chestertown?

The best way to find walking trails or routes in Chestertown is with the Pacer Walking App. You can find walking trails or routes with real user activities, images, and reviews in Pacer. Just download the Pacer Walking App today and start exploring with the interactive map of walking trails and routes.

Explore the best walking trails and routes in Chestertown. Explore scenic nature walks, urban adventures, and hidden gems right in your city. Start your journey today and uncover the best walking trails & routes near you with this curated list from Pacer Walking App.

Length

0~5 km5~10 km10~20 kmMore than 20 km

Showing 8 trails & routes

Sorted by: Most Reviewed

Stewart Mountain Trail

Caroline Fish Memorial Trail

Length 2.4 Km

Caroline Fish Memorial Trail walking route map in Chestertown

three barrel trail (yellow/red)

Length 0.9 Km

three barrel trail (yellow/red) walking route map in Chestertown

1 - 8 of 8

Explore More Trails & Routes in New York

Camillus Park- Green Trail

5.0 · 1 Review

Burnet Park Holiday Trek

5.0 · 1 Review

Camillus Park-Red Trail

5.0 · 1 Review

Elmwood Park & Trails Behind Corcoran High School

5.0 · 1 Review

Onondaga Park in Strathmore

5.0 · 1 Review

Westhill High School Track

5.0 · 1 Review

Solvay High School Track-Earl Hadley Stadium

5.0 · 1 Review

Camillus Park-Blue Trail

5.0 · 1 Review

Frequently Asked Questions About Trails & Routes Near Chestertown

Which is the best trail or route to walk in Chestertown?

Pacer allows you to create walking clubs for friendly competitions with your walking community or have a discussion about any health-related topics easily. Pacer is the best walking app for finding walking clubs.

What is the longest trail or route in Chestertown?

How many walking trails or routes are in Chestertown?

How do I find walking trails or routes near me in Chestertown?

Last updated: Dec 17, 2025

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