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Chesapeake

Chesapeake

The best running trails in Chesapeake city

4.0

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498

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Running in Chesapeake city is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes in Chesapeake city—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: October 25, 2025

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1. Indian River Park loop — Virginia Beach

3.75km

00:23

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

2. Stumpy Lake Loop — Virginia Beach

8.51km

00:55

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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3. The Hague loop from York Street/Freemason

9.66km

01:00

20m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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4. The Hague loop from Civic Plaza

18.7km

01:56

20m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Expert

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5. Running loop from York Street/Freemason

13.8km

01:25

20m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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6. The Hague loop from MacArthur Square

7.86km

00:49

20m

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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7. Running loop from Hardee Point

6.13km

00:38

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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8. Running loop from Harbour View

4.83km

00:30

10m

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

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9. Running loop from MacArthur Square

10.9km

01:07

20m

10m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Intermediate

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10. Running loop from Greenbrier

4.91km

00:30

Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

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

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The best running trails in Chesapeake city

1. Indian River Park loop — Virginia Beach

2. Stumpy Lake Loop — Virginia Beach

3. The Hague loop from York Street/Freemason

4. The Hague loop from Civic Plaza

5. Running loop from York Street/Freemason

6. The Hague loop from MacArthur Square

7. Running loop from Hardee Point

8. Running loop from Harbour View

9. Running loop from MacArthur Square

10. Running loop from Greenbrier

Most popular routes in Chesapeake city

Most popular attractions in Chesapeake city

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