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.
View route
The best running trails in Monroe County
By Fede from komoot
·
Updated June 2, 2026
If you've ever tried to plan jogging in Monroe County, you know how overwhelming the options can be. With so many routes out there, it's tough to tell which ones are genuinely worth your time and effort, and which are just filler. We get it – you want the highlights, not the guesswork.
That's where komoot comes in. Our community has mapped, ridden, and reviewed countless routes, and we've sifted through them to bring you a curated shortlist of the best jogging routes in Monroe County. This guide is your shortcut to finding the trails that truly deliver, saving you the hassle of sifting through endless possibilities. Expect coastal paths, scenic waterways, and varied terrain, with options ranging from easy paved sections to more challenging routes with slight elevation changes. Given that many of the most popular jogging trails in Monroe County are found in the Keys, you'll often find yourself running alongside the ocean.
If you only do one route, make it the Southernmost Point Buoy – Mile 0 of U.S. Highway 1 loop from Key West. This difficult 10.1 miles (16.2 km) path is a top favorite for a reason, offering iconic views and a real sense of accomplishment. For something a bit less demanding but still incredibly scenic, the Smathers Beach – Southernmost Hockey Club loop from Key West is a fantastic moderate option at 6.1 miles (9.9 km), perfect for a coastal run. We're confident you'll find a route you love here, and with more than 1,500 runners already exploring with komoot, you're in good company.
If you only do 3 of these routes
Compare these routes at a glance
Trail | Distance | Elevation | Difficulty |
|---|---|---|---|
| Southernmost Point Buoy – Mile 0 of U.S. Highway 1 loop from Key West | 16.1 km | 20 m | Hard |
| Southernmost Hockey Club – Smathers Beach loop from Stock Island | 13.4 km | 0 m | Moderate |
| Smathers Beach – Southernmost Hockey Club loop from Key West | 9.88 km | 0 m | Moderate |
| The Stoned Crab loop from Key West | 8.83 km | 0 m | Moderate |
| Dog Beach at Vernon Avenue – Historic House in Key West loop from Key West | 5.16 km | 10 m | Moderate |
| Smathers Beach – Historic House in Key West loop from Key West | 9.71 km | 10 m | Moderate |
| Dog Beach at Vernon Avenue – Smathers Beach loop from Key West | 7.22 km | 10 m | Moderate |
| Running loop from Stock Island | 6.37 km | 0 m | Moderate |
| Running loop from Florida Keys Marathon International Airport | 9.16 km | 10 m | Moderate |
| The Stoned Crab loop from Stock Island | 5.07 km | 0 m | Moderate |
Sign up to see all 10 routes
Sign up for free
2.
Southernmost Hockey Club – Smathers Beach loop from Stock Island
13.4km
01:24
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
3.
Smathers Beach – Southernmost Hockey Club loop from Key West
9.88km
01:02
0m
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.
Sign up for free
4.
The Stoned Crab loop from Key West
8.83km
00:54
0m
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
5.
Dog Beach at Vernon Avenue – Historic House in Key West loop from Key West
5.16km
00:32
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
6.
Smathers Beach – Historic House in Key West loop from Key West
9.71km
01:01
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
7.
Dog Beach at Vernon Avenue – Smathers Beach loop from Key West
7.22km
00:46
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
8.
Running loop from Stock Island
6.37km
00:39
0m
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
9.
Running loop from Florida Keys Marathon International Airport
9.16km
00:57
10m
10m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
10.
The Stoned Crab loop from Stock Island
5.07km
00:31
0m
0m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
View route
Sign up for free to see 5 more runs in Monroe County.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
See every route on the map
Tips from the Community
Stenio Melani
June 25, 2026, Smathers Beach
Smathers Beach is the largest public beach in Key West, Florida, famous for its long stretch of white sand, exceptionally calm waters, and the beautiful setting of tropical palm trees.
Translated by Google•
0
0
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.
2
0
der Kuhn
February 5, 2025, Southernmost Point Buoy
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
Translated by Google•
1
0
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.
0
0
Qrist
October 18, 2024, Key West International Airport
This airport (ICAO: KEYW, IATA: EYW) is the southernmost airport of continental USA.
0
0
In the early 20th century Marathon was the center of shipping operations in the region. Ships from Havana and other Caribbean locations would dock near the railway to offload their goods to trains heading north. However, this would all come to end in 1935 when a large storm damaged the rail lines and the highway soon replaced the railroad.
1
0
Wanderhase🐰
March 18, 2024, Southernmost Point Buoy
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's only a few minutes walk to the city center. In fact, Southernmost Point is not the southernmost point of Key West. This is located on the US Navy base next door. Because Key West is an island, the southernmost point of the continental USA is near Flamingo in the Everglades. In October 2017, the large painted buoy that marks the southernmost point of the continental United States was restored for the final time. Before that, the buoy, which is one of the most photographed subjects in the Florida Keys, was somewhat affected by Hurricane Irma. Local artist Danny Acosta was responsible for the new painting with the help of a few other people. On January 1, 2022, the buoy was set on fire by two men. The two vandals had placed a Christmas tree directly in front of the buoy and set it on fire, which caused it to fall onto the buoy and damage it.
Translated by Google•
9
0
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.
Get inspired with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.
Didn’t find what you were looking for?
Check out more Running Trails & Routes throughout Monroe County below and find the perfect route in your destination.
IslamoradaMarathonKey LargoEverglades National ParkFlorida Keys WildernessNorth Key LargoTavernierMarjory Stoneman Douglas WildernessKey Colony BeachJohn Pennekamp Coral Reef State ParkStock IslandBig Coppitt KeyDuck KeyKey West National Wildlife RefugeKey WestGreat White Heron National Wildlife Refuge
Explore more
Browse the best Running Trails & Routes in other regions.
CaliforniaIllinoisColoradoNew YorkMassachusettsHawaiiTexasFloridaHonolulu CountyOregonUtahMaui CountyMaineVirginiaWashingtonArizonaPennsylvaniaMarylandConnecticutMinnesotaMissouriNew JerseyGeorgiaNorth CarolinaSouth CarolinaAlaskaNevadaTennesseeAppalachian MountainsOhioNew HampshireMichiganKauaʻi CountyNebraskaRhode IslandKentuckyHawaiʻi CountyKansasOklahomaWisconsinIndianaNew MexicoOregon Islands WildernessSouth DakotaIdahoWyomingIowaNorth DakotaSan FranciscoSan FranciscoWashington D.CDistrict Of ColumbiaVermontDelawareArkansasPuerto RicoSan JuanSan Juan MunicipioCatañoWest VirginiaLouisianaGuaynabo MunicipioGuaynaboAlabamaBayamónMontanaCata O MunicipioToa Baja MunicipioCarolinaCarolina MunicipioTrujillo AltoMississippiToa BajaToa AltaToa Alta MunicipioAguadaAguada MunicipioLoíza MunicipioTrujillo Alto MunicipioLoízaBayamón MunicipioRincónRincon MunicipioDoradoDorado MunicipioAguadillaAguadilla MunicipioAñascoAasco MunicipioMoca MunicipioMocaGuamVega Alta MunicipioVega BajaVega Baja MunicipioLajas MunicipioVega AltaLuquillo MunicipioUnited States Virgin IslandsLajasCaguasCaguas MunicipioIsabela MunicipioIsabelaSalinasSalinas MunicipioVillalbaSan LorenzoGuraboVillalba MunicipioGurabo MunicipioSan Lorenzo MunicipioAibonitoAibonito MunicipioCidraCidra MunicipioRío GrandeCayeyCayey MunicipioCoamo MunicipioCoamoMayagüezSan GermánSan Germán MunicipioCanóvanasLuquilloCanóvanas MunicipioRío Grande MunicipioCabo RojoCabo Rojo MunicipioLas PiedrasComer�O MunicipioFajardoLas Piedras MunicipioFajardo MunicipioComeríoJuana DíazJuana DíazHumacao
