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United States
Monroe County

Islamorada

The best running trails around Islamorada

5.0

(1)

137

runners

9

runs

Jogging routes around Islamorada are characterized by their unique coastal setting within the Florida Keys, offering flat terrain ideal for running. The region features extensive paved pathways, including sections of the Florida Keys Overseas Heritage Trail, which provides continuous waterside views. Natural features like mangrove forests and tropical hammocks are accessible through various state parks and preserves, contributing to the diverse running environment. The low elevation gain across routes reflects the Keys' geological composition.

Best jogging routes around Islamorada

  • The…

Last updated: June 24, 2026

18

runners

#1.

Islamorada loop from Teatable Key

10.5km

01:05

10m

10m

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

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Moderate

21

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

11

runners

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

Easy

9

runners

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

Moderate
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Popular around Islamorada

Florida Keys Overseas Heritage Trail — A walk in paradise

Road Cycling Routes around Islamorada

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Florida Keys Overseas Heritage Trail — A walk in paradise

Hiking Collection by

Sue

Tips from the Community

Bear S.
October 31, 2025, Windley Key Fossil Reef Geological State Park

A small historical place. It's also interesting that there's still forest to be seen there.

Translated by Google

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Sue
April 4, 2025, Islamorada

Islamorada is a small village comprised of five islands in the heart of the Florida Keys, with some areas just one mile wide and five feet above sea level. Known as the “Sportfishing Capital of the World,” it features many professional charter boats and excellent fishing opportunities. There are many parks, open spaces, and several village beaches with tropical-themed bars, for plenty of options to enjoy the fresh, local seafood the town is famous for. While you're here, be sure to explore the Morada Way Art and Cultural District for a taste of local culture.

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Windley Key Fossil Reef Geological State Park, a former quarry, offers a glimpse into the Florida Keys' history. Henry Flagler's Overseas Railroad, built in the early 1900s, relied on its limestone. Later, the quarry yielded polished “keystone,” a decorative limestone unique to this area until the 1960s. The Hurricane Monument in Islamorada, at Mile Marker 82, is constructed from keystone extracted here. The park features several short loop trails throughout the grounds, where you can view the exposed fossilized coral reefs and remnants of the original quarry equipment. There is a drinking fountain, restrooms, and a lovely bench, perfect for a place to take a break under a canopy of hammock trees. The park is open daily from 8 am until sundown, with a $2.50 entrance fee. The visitor center operates Thursday–Monday, 8 am to 5 pm.

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Frequently Asked Questions

What types of running routes can I find in Islamorada?

Islamorada offers a variety of running experiences, primarily featuring scenic coastal paths and sections of the Florida Keys Overseas Heritage Trail. You'll find routes that wind through tropical hammocks, alongside mangrove forests, and over historic bridges with stunning ocean views. Many routes are paved, making them suitable for various running styles.

Are there any easy or beginner-friendly jogging paths in Islamorada?

Yes, for those looking for a less strenuous run, the region offers easier options. A great choice is the Running loop from Long Key State Park, which is approximately 3.8 km long and has minimal elevation gain, perfect for a relaxed jog or a beginner's outing.

Where can I find longer running trails for endurance training?

For longer distances, consider routes that incorporate sections of the Overseas Heritage Trail. The Long Key Bridge loop from Long Key State Park offers a moderate 12.8 km run with continuous scenic views over the water, ideal for building endurance.

Are there any circular jogging routes available?

Absolutely! Many of the routes in Islamorada are designed as loops, allowing you to start and finish in the same location. Examples include the Islamorada loop from Teatable Key (10.5 km) and the Islamorada loop from Islamorada (6.5 km), both offering diverse scenery.

What kind of natural landmarks or viewpoints can I expect along the running routes?

Islamorada's running routes are rich with natural beauty. You'll often find yourself running alongside the turquoise waters of the Atlantic, with opportunities to spot marine life. The Windley Key Fossil Reef Geological State Park offers unique trails through an exposed coral reef, while the boardwalk at Anne's Beach Park provides tranquil views through mangroves. Many routes also feature historic bridges, offering panoramic vistas.

Are the running trails in Islamorada suitable for families or those with dogs?

Many of Islamorada's paved pathways and sections of the Overseas Heritage Trail are suitable for families, offering relatively flat terrain. For dog owners, it's generally advisable to check specific park regulations, but many public pathways allow leashed dogs. Always ensure your pet is comfortable with the heat and bring plenty of water for both of you.

What is the best time of year or day to go jogging in Islamorada?

The cooler months from November to April are generally ideal for jogging in Islamorada, as temperatures are more moderate. During the warmer months, it's best to run early in the morning or late in the afternoon to avoid the peak heat and humidity. Always stay hydrated and wear appropriate sun protection.

What are the typical terrain and elevation like on Islamorada's running routes?

The terrain in Islamorada is predominantly flat, characteristic of the Florida Keys. Most running routes, especially those on the Overseas Heritage Trail and dedicated pathways, are paved. You'll experience very minimal elevation changes, making it an excellent location for runners who prefer flat, consistent surfaces.

Are there any running routes that pass by cafes or places to eat?

While specific routes may not directly pass by cafes, Islamorada is well-equipped with dining options. Many routes are accessible from areas with local eateries. For example, the Islamorada loop from Theater of the Sea starts near a popular attraction, and you'll find various establishments along the main Overseas Highway after your run.

How accessible are the jogging routes by public transport or car, and is parking available?

Access to jogging routes in Islamorada is primarily by car, with ample parking often available at state parks, public beaches like Anne's Beach, and designated trailheads along the Overseas Heritage Trail. Public transport options are limited, so driving is generally the most convenient way to reach most starting points.

What do other runners enjoy most about jogging in Islamorada?

Runners frequently praise the unparalleled scenic beauty of Islamorada's routes, especially the continuous waterside views along the Overseas Heritage Trail. The flat, paved surfaces are often highlighted as a positive, providing a comfortable and consistent running experience. The opportunity to spot local wildlife and enjoy the tropical environment also adds to the appeal.

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