The best running trails in Monroe County

This Key West jogging route offers a vibrant tour through the island's most famous landmarks, blending urban exploration with coastal scenery. You'll experience the unique atmosphere of Historic Key West as you jog past charming streets and enjoy calm Atlantic Ocean views, culminating at the iconic Southernmost Point Buoy. The terrain is mostly flat and paved, making for a smooth running experience, but the distance makes it a challenging endeavor.

Planning your run requires a bit of strategy, especially if you want to avoid the biggest crowds. Both the Southernmost Point Buoy and Mile 0 of U.S. Highway 1 are major tourist attractions, so an early morning start is highly recommended to secure parking and enjoy a more peaceful experience. Remember to stay hydrated, as Key West's tropical climate means you'll be jogging in warm, humid conditions.

This 10.0-mile (16.1 km) loop, with a minimal 59 feet (18 metres) of elevation gain, is rated difficult due to its length and takes approximately 1 hour and 40 minutes to complete. It's an excellent choice for experienced joggers seeking a substantial workout combined with sightseeing, offering a unique opportunity to run through a historically and geographically significant part of the continental United States.

Lace up for a refreshing 6.1-mile (9.8 km) jogging loop around Key West, tracing the scenic Smathers Beach and winding through historic neighborhoods. This moderate route, with a negligible 30 feet (9 metres) of elevation gain, offers a fantastic blend of tropical waterfront views, coconut tree-lined stretches, and the charming architecture of Old Town. Expect mostly paved surfaces, with some firm sand near the waterline on Smathers Beach, making for a smooth run that takes about 1 hour and 2 minutes.

This accessible route is perfect for those looking to combine exercise with sightseeing. While specific parking information isn't detailed, the trail's central location in Key West means easy access from various points. Given Key West's tropical climate, planning your run for the cooler parts of the day, such as early morning or late afternoon, will enhance your experience.

What makes this loop truly special is its ability to weave together Key West's natural beauty with its rich past. You'll pass significant historical sites like the East Martello Museum and the West Martello Tower, offering glimpses into the island's heritage. The route also runs parallel to South Roosevelt Boulevard, famously known as the Jimmy Buffett Memorial Highway, adding a touch of local lore to your journey.

Lace up your shoes for the Southernmost Hockey Club – Smathers Beach loop from Stock Island, a delightful jogging route that hugs the Key West coastline. You'll mostly be on paved surfaces, enjoying extensive ocean views and the vibrant atmosphere of Smathers Beach, known for its white sand and swaying coconut trees. It's a flat, easy-going path perfect for soaking in the Florida Keys scenery.

This moderate 8.3-mile (13.4 km) loop has a negligible 21 feet (6 metres) of elevation gain, making it accessible for nearly everyone. You can expect to complete the run in about 1 hours and 23 minutes. While the trail starts from Stock Island, parking is generally available near Smathers Beach, a popular hub for activities.

Smathers Beach itself is a highlight, not just for its beauty but also for its historical significance as the landing point for Diana Nyad's epic swim from Cuba. The area is bustling with beach volleyball, jet-skiing, and parasailing, adding to the lively coastal vibe you'll encounter on this scenic Key West jogging trail.

The Stoned Crab loop offers a refreshing jogging experience through Key West, blending paved paths with glimpses of coastal beauty. You'll pass by tranquil mangrove island scenery and enjoy ocean views, with the unique highlight of Dog Beach at Vernon Avenue, where you might see dogs playing. This route is mostly flat, making it a pleasant and accessible option for a steady run.

Starting conveniently at The Stoned Crab restaurant, this moderate 5.5-mile (8.8 km) loop has a minimal 12 feet (4 metres) of elevation gain and takes about 54 minutes to complete. Parking is available at the starting point. To make the most of your run, consider heading out in the cooler morning or late afternoon hours, and always remember to bring water.

What sets this route apart is its inclusion of Dog Beach, a small, distinctive stretch of shoreline where dogs are welcome off-leash. While the beach itself can be sandy and rocky, it adds a unique point of interest to your run. The Stoned Crab restaurant also provides a great post-run dining option, known for its fresh seafood.