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Routes
Running Trails
United States

Monroe County

Routes
Running Trails
United States

Monroe County

The best running trails in Monroe County

59runs

4.5

(13)

984 people ran here

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.

The Stoned Crab loop from Key West
Intermediate

01:29

14.4km

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

01:52

18.1km

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

00:55

8.85km

Key West International Airport – East Martello Museum loop from Stock Island
Intermediate

00:56

9.06km

Dog Beach at Vernon Avenue loop from Downtown
Intermediate

00:50

8.13km

Dog Beach at Vernon Avenue loop from Stock Island
Intermediate

01:17

12.5km

Running loop from Historic Seaport
Intermediate

00:41

6.58km

Running loop from Stock Island
Intermediate

00:39

6.37km

Dog Beach at Vernon Avenue – Key West International Airport loop from Casa Marina
Intermediate

01:02

9.84km

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  1. Map data © OpenStreetMap contributors
    1
    1

    The Stoned Crab loop from Key West

    01:29

    14.4km

    6:11/km

    10m

    10m

    Intermediate

    4.7

    (3)

    118

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  2. Map data © OpenStreetMap contributors
    2
    2

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

    01:52

    18.1km

    6:11/km

    10m

    10m

    Expert

    4.7

    (3)

    93

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

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  4. Map data © OpenStreetMap contributors
    3
    3

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

    00:55

    8.85km

    6:10/km

    10m

    10m

    Intermediate

    5.0

    (1)

    56

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  5. Map data © OpenStreetMap contributors
    4
    4

    Key West International Airport – East Martello Museum loop from Stock Island

    00:56

    9.06km

    6:14/km

    0m

    0m

    Intermediate

    5.0

    (2)

    57

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  6. Map data © OpenStreetMap contributors
    5
    5

    Dog Beach at Vernon Avenue loop from Downtown

    00:50

    8.13km

    6:13/km

    10m

    10m

    Intermediate

    35

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  7. Map data © OpenStreetMap contributors
    6
    6

    Dog Beach at Vernon Avenue loop from Stock Island

    01:17

    12.5km

    6:10/km

    10m

    10m

    Intermediate

    31

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  8. Map data © OpenStreetMap contributors
    7
    7

    Running loop from Historic Seaport

    00:41

    6.58km

    6:10/km

    10m

    10m

    Intermediate

    5.0

    (1)

    52

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  9. Map data © OpenStreetMap contributors
    8
    8

    Running loop from Stock Island

    00:39

    6.37km

    6:10/km

    0m

    0m

    Intermediate

    4.0

    (1)

    12

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
  10. Map data © OpenStreetMap contributors
    9
    9

    Dog Beach at Vernon Avenue – Key West International Airport loop from Casa Marina

    01:02

    9.84km

    6:21/km

    10m

    10m

    Intermediate

    49

    Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
10
10

East Martello Museum – Key West International Airport loop from New Town

00:46

7.53km

6:09/km

0m

0m

Intermediate

22

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

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Last updated:
September 2, 2025

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