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Running Trails
United States
Monroe County

Stock Island

The best running trails around Stock Island

4.3

(5)

1,015

runners

58

runs

Jogging around Stock Island offers a unique blend of natural beauty and recreational opportunities. The region is characterized by its tranquil atmosphere, working waterfronts, and diverse natural features. Joggers can explore lush botanical gardens with winding trails, experience scenic coastal paths along the Florida Keys Overseas Heritage Trail, and enjoy views of mangrove islands. Many routes feature mostly paved surfaces and minimal elevation gain, making them accessible for various fitness levels.

Best jogging routes around Stock Island

  • The most popular…

Last updated: May 18, 2026

4.0

(1)

61

runners

#1.

Southernmost Hockey Club – Smathers Beach loop from Stock Island

13.4km

01:24

10m

10m

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

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Moderate

4.0

(2)

16

runners

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

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

Moderate

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

Hard
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Popular around Stock Island

Cycling around Stock Island

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Tips from the Community

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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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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Qrist
October 18, 2024, East Martello Museum

This museum exhibits local history and art. The building is the best preserved Martello tower in the country.

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This airport (ICAO: KEYW, IATA: EYW) is the southernmost airport of continental USA.

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Frequently Asked Questions

How many running routes are available in Stock Island?

Stock Island offers a good selection of running routes, with over 60 different trails available for exploration. These routes cater to various fitness levels, from easy strolls to more challenging long-distance runs.

Are there easy running routes for beginners or casual joggers in Stock Island?

Yes, Stock Island has several easy running routes perfect for beginners or those looking for a casual jog. Many trails feature mostly paved surfaces and minimal elevation gain, making them accessible. There are 8 easy routes available, with some extending up to 3 miles for a comfortable workout.

What kind of terrain can I expect on Stock Island's running trails?

You can expect a variety of terrain on Stock Island's running trails. Many routes feature mostly paved surfaces, ideal for a smooth run. However, you'll also find natural settings, including winding trails within the Key West Tropical Forest & Botanical Garden, and scenic stretches along the Florida Keys Overseas Heritage Trail which may have varied surfaces. The region is generally flat, with minimal elevation changes.

Are there any family-friendly jogging paths in Stock Island?

Yes, Stock Island offers family-friendly jogging paths. The mostly paved and flat routes are suitable for families. For instance, the trails within the Key West Tropical Forest & Botanical Garden are a great option, offering diverse scenery and wildlife spotting opportunities that can engage children.

Can I bring my dog on the running trails in Stock Island?

Yes, some running trails in Stock Island are dog-friendly. A notable option is The Stoned Crab – Dog Beach at Vernon Avenue loop from Stock Island, which passes by a dedicated dog beach. Always ensure your dog is on a leash and check specific trail regulations before heading out.

What natural features or viewpoints can I see while running in Stock Island?

Jogging in Stock Island offers beautiful natural features and viewpoints. You can experience lush botanical gardens, scenic coastal paths with ocean views, and tranquil mangrove island scenery. The Key West Tropical Forest & Botanical Garden provides a unique immersion into subtropical flora and fauna, while sections of the Florida Keys Overseas Heritage Trail offer stunning ocean vistas.

Are there any interesting landmarks or attractions near the jogging routes?

While Stock Island itself is known for its natural beauty, several notable attractions are nearby. You can find landmarks such as the Southernmost Point Buoy, the Key West Lighthouse, and the historic Ernest Hemingway Home and Museum within easy reach, particularly on routes extending towards Key West.

Are there any circular running routes in Stock Island?

Yes, Stock Island features several circular running routes. For example, the Running loop from Stock Island is a moderate 4.0-mile (6.4 km) trail that takes you through accessible paved areas, offering a convenient loop experience.

What do other runners enjoy most about jogging in Stock Island?

The running experience in Stock Island is highly rated by the komoot community, with an average score of 4.7 stars from over 10 reviews. Runners often praise the tranquil atmosphere, the beautiful coastal views, and the opportunity to explore lush botanical gardens. The variety of routes, from easy paved paths to longer coastal stretches, is also frequently highlighted.

Is there parking available near the running trails in Stock Island?

Yes, parking is generally available near many of the running trails and recreational areas in Stock Island. For instance, Bernstein Park, which offers a fitness court and open spaces, has parking facilities. It's always a good idea to check specific starting points for designated parking areas.

What is the best time of year to go running in Stock Island?

The best time of year to go running in Stock Island is typically during the cooler, drier months, from late fall through spring (roughly November to April). During this period, temperatures are more moderate, and humidity is lower, making for more comfortable outdoor activity. Summers can be very hot and humid, with a higher chance of rain.

Are there any routes that offer extensive coastal views?

Absolutely. Many routes in Stock Island provide extensive coastal views. A great example is Smathers Beach – Southernmost Hockey Club loop from Stock Island, which offers scenic stretches along Smathers Beach with beautiful ocean vistas. Parts of the Florida Keys Overseas Heritage Trail also provide stunning ocean scenery.

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