The best running trails in Monroe County

This 5.4-mile (8.7 km) jogging route through Key West's historic district offers a moderate workout with just 28 feet (9 metres) of elevation gain, typically completed in about 53 minutes. You'll wind through charming residential streets, past pastel-hued conch-style houses and impressive Victorian gingerbread architecture. The route provides a unique immersion into the island's atmosphere, showcasing its distinctive character and historic landmarks like St. Paul's Episcopal Church.

Planning your run is straightforward, as the terrain is largely flat and paved, making it accessible for most fitness levels. To truly soak in the ambiance and avoid the busiest times, aim for an early morning start before the main tourist activity begins. Parking is available in the historic district, but arriving early is recommended to find a good spot, especially during high season.

What makes this Key West historic house jogging loop particularly special is its deep connection to the island's past. You'll pass by St. Paul's Episcopal Church, Florida's oldest church south of St. Augustine, a testament to the community's resilience through natural disasters. This route is more than just a jog; it's a moving tour through Key West's unique history and architectural heritage, offering a memorable experience for those interested in the island's story.

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.

The Historic House in Key West loop offers a delightful jogging experience, blending a moderate workout with a deep dive into the island's unique architectural heritage. As you cover the 4.4 miles (7.1 km) with only 28 feet (8 metres) of elevation gain, you'll wind through charming residential streets, admiring colorful Conch houses, grand Victorian mansions, and homes with Bahamian influences. The route provides a smooth, paved surface, making it accessible for nearly all fitness levels and a perfect way to explore the historic district.

Planning your visit is straightforward; the route is largely flat and well-suited for a leisurely pace, taking about 44 minutes to complete. To make the most of your run and avoid the heat, consider heading out in the early morning or late afternoon. Parking can typically be found on residential side streets, but it's always wise to check for local restrictions. This loop is an excellent option for those seeking scenic views and a cultural jog without significant physical demands.

What makes this Key West loop particularly special is its focus on the island's past, offering a unique perspective on its well-preserved historic homes and charming residential streets. The blend of cultural insight and physical activity in a tropical setting creates a memorable jogging experience, setting it apart from more generic running trails. It's a fantastic way to see the historic houses of Key West while enjoying a refreshing jog.

This easy 2.9-mile (4.7 km) jogging route offers a delightful blend of Key West's coastal charm and historic architecture, with a minimal 24 feet (7 metres) of elevation gain over its 29-minute duration. You'll experience the unique Dog Beach, a small, pet-friendly pocket beach where dogs can play off-leash, before transitioning into the picturesque streets of Old Town. The flat, paved terrain makes for a comfortable run, allowing you to soak in the views of Victorian gingerbread houses and other historic landmarks.

To best enjoy this Key West jogging route, plan your visit during the cooler, drier months from November to May. Starting your run in the early morning or late afternoon will help you avoid the island's peak heat and crowds. While specific parking for this loop isn't detailed, general street parking is available throughout Key West, so allow extra time to find a spot.

What makes this route particularly special is its dual appeal: it's one of the few places in Key West where dogs are officially allowed off-leash to swim, making it a fantastic option for pet owners. Beyond the beach, the route winds through a vibrant part of Key West's historic district, offering a glimpse into the island's rich past through its well-preserved homes and distinctive architectural styles.