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Running Trails
United States

Monroe County

The best running trails in Monroe County

4.4

(8)

1,378

runners

85

runs

Jogging routes in Monroe County offer a diverse range of outdoor experiences, characterized by extensive trail networks and scenic natural features. The region features routes alongside rivers and lakes, through wooded areas, and across varied terrain. Many trails are multi-use, accommodating different fitness levels from easy paved paths to more challenging routes with elevation changes. Dedicated park systems and green spaces provide accessible environments for running enthusiasts.

Best jogging routes in Monroe County

  • The most popular jogging route is The…

Last updated: May 1, 2026

92

runners

#1.

Southernmost Point Buoy – Mile 0 of U.S. Highway 1 loop from Key West

16.1km

01:41

20m

20m

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

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Hard

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

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

Moderate

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

Easy

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

Moderate

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

Moderate

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

Moderate

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

Moderate

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

Easy

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

Moderate
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Popular around Monroe County

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Other adventures in Monroe County

Florida Keys Overseas Heritage Trail — A walk in paradise

Hiking Collection by

Sue

Tips from the Community

Bloggmaus
July 16, 2025, Key West Shipwreck Treasure Museum & Observation Tower

The Key West Shipwreck Treasure Museum houses a 20-meter-high observation tower offering views of the city and the ocean. The observation tower is part of the Key West Shipwreck Treasure Museum, which celebrates the city's maritime history. Visitors can learn about the dangers of shipwrecks and the salvage industry that once made Key West prosperous.

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Sue
April 8, 2025, Smathers Beach

Smathers Beach, named after George Smathers (1913-2007), a former U.S. Senator from Florida and a friend of President John F. Kennedy, is the largest public beach in Key West, stretching about half a mile along the Atlantic Ocean. It begins at mile marker zero and is beautifully lined with coconut trees. On September 2, 2013, long-distance swimmer Diana Nyad made history by arriving at Smathers Beach after swimming 110 miles from Havana, Cuba, becoming the first person to complete the journey without a shark cage.

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Very beautiful church with a wooden ceiling and colorful windows. Well worth a visit.

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It is very interesting to see how long the wooden houses, which are "simply" built from a Central European perspective, can withstand the organs etc.

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It is quite busy here at lunchtime. It is better to get up early, then you will be able to get an uninterrupted picture. The Southernmost Point is considered the southernmost point in the continental United States and is located on the last of the Florida Keys, Key West. It is located on the edge of the city of Key West in the Upper Duval district on the corner of Whitehead Street and South Street. It is only a few minutes' walk to the city center. The Southernmost Point is actually not the southernmost point in Key West. This is located on the US Navy base next door. Since Key West is an island, the southernmost point in the continental USA is near Flamingo in the Everglades. Source Wikipedia

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Entrance fee: $21 Address: 1 Whitehead St. Key West, Florida 33040 The aquarium opens at 9am and closes at 6pm. It is a very small aquarium and the price is quite high, whether it is worth it is in the eye of the beholder.

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The oldest house in South Florida is located at 322 Duval Street in Key West. The house and gardens are open to the public every day except Sunday and Wednesday from 10 a.m. to 4 p.m. Admission is $5.00. Staff and docents are available to provide historical information about the house and family and to answer questions. The house features family portraits and original furnishings, as well as other historical pieces, ship models and documents that tell the story of old Key West. At the back of the house is a spacious, peaceful garden where the benches invite you to sit and reflect. There you will see the only surviving Cook House in South Florida.

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St. Paul's Episcopal Church enjoys a prominent location on Key West's busy Duval Street. But even without this enviable property, the church would be hard to miss. On sunny days, the white facade stands out brilliantly against the bright blue Key West sky. Inside, you'll find a peaceful sanctuary from the bustling city.

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Frequently Asked Questions

How many running routes are available in Monroe County?

Monroe County offers a wide selection of running routes, with over 80 different options to explore. These routes cater to various preferences, from easy strolls to more challenging runs.

What kind of terrain can I expect on jogging routes in Monroe County?

Jogging routes in Monroe County, particularly around Key West and Stock Island, are characterized by coastal paths, scenic waterways, and generally flat terrain. While most routes have minimal elevation changes, some, like the Southernmost Point Buoy – Mile 0 of U.S. Highway 1 loop from Key West, do feature slight undulations, adding a touch of variety to your run.

Are there any easy running routes suitable for beginners in Monroe County?

Yes, Monroe County has several easy running routes perfect for beginners or those looking for a relaxed jog. An excellent option is the St. Pauls Episcopal Church – Southernmost Point Buoy loop from Key West, which is just over 2.6 miles (4.2 km) long and has an easy difficulty rating.

What are some scenic landmarks or natural features I can see while running in Monroe County?

Many running routes in Monroe County offer picturesque views and pass by notable landmarks. You can run past the iconic Southernmost Point Buoy, explore areas near Fort Zachary Taylor State Park, or enjoy the coastal scenery around Smathers Beach. Other natural highlights include the Guy Bradley Trail and the John Pennekamp Coral Reef State Park area.

Are there any dog-friendly running routes in Monroe County?

Yes, several routes in Monroe County are suitable for running with your dog. For example, the popular The Stoned Crab – Dog Beach at Vernon Avenue loop from Stock Island is specifically named for its dog-friendly features, allowing you and your canine companion to enjoy the coastal scenery together.

What do other runners enjoy most about the trails in Monroe County?

The running trails in Monroe County are highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the beautiful coastal views, the unique Key West atmosphere, and the accessibility of many routes for different fitness levels.

Are there any circular running routes in Monroe County?

Absolutely! Many of the best running routes in Monroe County are circular, offering a convenient way to start and end your run in the same location. Examples include the The Stoned Crab loop from Stock Island and the Southernmost Point Buoy – Historic House in Key West loop from Key West.

What is the typical length of jogging routes in Monroe County?

Running routes in Monroe County vary significantly in length. You can find shorter options, like the St. Pauls Episcopal Church – Southernmost Point Buoy loop from Key West at 2.6 miles (4.2 km), up to longer, more challenging runs such as The Stoned Crab – Dog Beach at Vernon Avenue loop from Stock Island, which spans 10.9 miles (17.6 km).

Are there any running routes that pass by lakes or other bodies of water?

Monroe County is defined by its coastal environment, so many running routes offer stunning views of the ocean and pass by beaches. While large freshwater lakes are less common, you can find routes near areas like Eco Pond and enjoy the unique marine landscapes of the Florida Keys.

Are there running trails with parking available in Monroe County?

Yes, many running routes in Monroe County are accessible with parking nearby, especially those originating from popular areas like Key West and Stock Island. While specific parking details vary by location, public parking lots and street parking are generally available in these areas, making it convenient to access the trails.

What are the best times of year for running in Monroe County?

Monroe County, being in South Florida, offers pleasant running conditions during the cooler, drier months from late fall through spring (roughly November to April). Summers can be very hot and humid, so early morning or late evening runs are recommended during those times to avoid the peak heat.

Can I find family-friendly running trails in Monroe County?

Yes, many of the easier and moderate routes in Monroe County are suitable for families. The generally flat terrain and scenic coastal paths make for enjoyable outings. Consider shorter, paved sections in parks or along beaches for a pleasant family run.

Most popular routes in Monroe County

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