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Monroe County

Monroe County

The best running trails in Monroe County

4.6

(14)

1,028

runners

runs

Running in Monroe County 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 Monroe County—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: December 5, 2025

4.7

(3)

132

runners

1. The Stoned Crab loop from Key West

14.4km

01:29

10m

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

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Moderate

4.7

(3)

runners

2. The Stoned Crab – Dog Beach at Vernon Avenue loop from Stock Island

18.1km

01:52

10m

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

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Hard

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runners

3. Dog Beach at Vernon Avenue – Key West Harbour Walk loop from Historic Seaport

15.7km

01:37

20m

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

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Hard

5.0

(1)

runners

4. Mile 0 of U.S. Highway 1 loop from White Street Gallery District

8.85km

00:55

10m

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

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Moderate

5.0

(1)

runners

5. Running loop from Historic Seaport

6.58km

00:41

10m

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

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Moderate

runners

6. East Martello Museum – Key West Beach loop from New Town

8.26km

00:51

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

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Moderate

runners

7. Dog Beach at Vernon Avenue loop from New Town

7.20km

00:44

10m

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

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Moderate

5.0

(1)

runners

8. Dog Beach at Vernon Avenue – Mile 0 of U.S. Highway 1 loop from Bahama Village

8.44km

00:52

10m

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

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Moderate

runners

9. Key West International Airport – East Martello Museum loop from White Street Gallery District

9.32km

00:58

10m

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

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Moderate

runners

10. Key West Beach – The Stoned Crab loop from New Town

9.55km

01:00

10m

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

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Moderate

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Didn’t find what you were looking for?

Check out more Running Trails & Routes throughout Monroe County below and find the perfect route in your destination.

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The best running trails in Monroe County

1. The Stoned Crab loop from Key West

2. The Stoned Crab – Dog Beach at Vernon Avenue loop from Stock Island

3. Dog Beach at Vernon Avenue – Key West Harbour Walk loop from Historic Seaport

4. Mile 0 of U.S. Highway 1 loop from White Street Gallery District

5. Running loop from Historic Seaport

6. East Martello Museum – Key West Beach loop from New Town

7. Dog Beach at Vernon Avenue loop from New Town

8. Dog Beach at Vernon Avenue – Mile 0 of U.S. Highway 1 loop from Bahama Village

9. Key West International Airport – East Martello Museum loop from White Street Gallery District

10. Key West Beach – The Stoned Crab loop from New Town

Other adventures in Monroe County

Most popular routes in Monroe County

Most popular attractions in Monroe County

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