4.5
(11)
521
riders
17
rides
Road cycling around Crestview, Florida, offers varied terrain in the Florida Panhandle, known as the "Hub City" for its central location. The region features one of Florida's highest points at 236 feet above sea level, providing rolling hills that contrast with the state's typically flat landscapes. Cyclists can explore routes through diverse natural areas, including forests, wetlands, and along rivers like the Shoal River, offering a more engaging ride experience.
Last updated: June 30, 2026
4.5
(2)
112
riders
Embark on a unique road cycling adventure with the Cincinnati Flying Pig Statues – Serpentine Wall loop, a moderate 27.6-mile (44.4 km) route that offers a delightful blend of urban…
17
riders
151km
07:14
1,560m
1,560m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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5
riders
65.9km
03:23
880m
880m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
5
riders
52.6km
02:21
370m
370m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
7
riders
34.4km
01:41
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Crestview
Lots of hills! But stop mid run at Coffee emporium before you run back to your car!
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Wasson Way is a new, still-developing multi-use greenway in Cincinnati, Ohio, aiming to transform over 6 miles of unused railway into a trail for pedestrians and cyclists. The trail extends from Victory Parkway near Xavier University through twelve local neighborhoods. As of now, Wasson Way is open from Ault Park to Montgomery Road. Future expansions are planned to connect the trail further east to the Little Miami Scenic Trail and westward to the Ohio River Trail, integrating it into the larger CROWN (Cincinnati Riding Or Walking Network), a 34-mile trail loop connecting various paths across the city.
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This public landing is along the Ohio River Trail is a nice spot to stop for a quick dip or to just enjoy the views over the water. It is also near the National Steamboat Monument and the Great American Ball Park.
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The Lunken Loop Trail is a popular 5-mile paved trail located in Cincinnati, Ohio, encircling the Lunken Airport. This flat, multi-use trail is great for walking, running, and biking. The loop offers a unique experience, with portions of the trail running adjacent to the airport, which allow you to watch planes take off and land. This viewpoint overlooks the open, green field on the southern end of the airport.
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The Cincinnati Observatory is the oldest professional observatory in the United States, at 178-year-old. Locally known as the Mt. Lookout Observatory, it allows public access for tours and regular viewings through both historical telescopes.
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Hyde Park Square is a beautiful, green micro-park in the middle of Hyde Park. The park has benches and a manicured green lawn. It is a great place for a rest while walking through Cincinnati.
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Ault Park is the city's fourth-largest park and was established in 1911 through the generous land donation by Levi Addison Ault and his wife, Ida May Ault. This spot is the heart of Ault Park. There is a Italian Renaissance-style Pavilion, constructed in 1930 with a large fountain in front of it. This elegant structure serves as a popular venue for weddings, dances, and private events, and provides visitors with panoramic views of the surrounding Little Miami River valley. Adjacent to the pavilion are the park's gardens, which feature the renowned Adopt-A-Plot program initiated in 1980, where volunteers maintain individual garden plots, contributing to the park's vibrant floral displays.
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Crestview, known as the "Hub City," offers a more varied terrain than typically found in Florida. You'll encounter rolling hills, as the region is one of the highest points in Florida at 236 feet above sea level. Routes often pass through diverse natural areas, including forests, wetlands, and along rivers like the Shoal River, providing a more engaging ride experience.
While many road cycling routes around Crestview are moderate, nearby paved trails offer excellent family-friendly options. The Blackwater Heritage State Trail in Milton, for example, provides 9.6 miles of smooth, well-maintained surfaces, often with restrooms. Twin Hills Park in Crestview also offers walking trails suitable for leisurely family strolls.
Road cycling routes in the Crestview area can take you through diverse natural landscapes. You might pass by the expansive Blackwater River State Forest, known for its scenic rivers and wildlife, or along the Shoal River, which features trails and overlooks. The route from Crestview to DeFuniak Springs, for instance, passes by Lake DeFuniak, offering picturesque views.
The road cycling routes in Crestview are generally considered moderate. While not mountainous, the rolling hills provide a more dynamic ride compared to flatter regions. For example, the route Cincinnati Flying Pig Statues loop from Riverbend Music Center covers 27.3 miles with an elevation gain of 469 feet, offering a good workout without being overly strenuous.
Yes, Crestview's central location allows for longer rides connecting to nearby towns. You can find routes extending to Marianna (134.9 km), Chipley (126 km), Bonifay (108.1 km), and East Milton (47.5 km). A notable moderate option is the 57.8-mile route from Crestview to DeFuniak Springs, featuring 753 feet of elevation gain.
The road cycling routes around Crestview are highly regarded by the komoot community, holding an average rating of 4.75 stars from 3 reviews. Over 200 road cyclists have used komoot to explore the varied terrain, appreciating the engaging rides offered by the region's rolling hills and natural scenery.
While Crestview features rolling hills rather than mountains, you can find routes with notable elevation gain. For example, the Ohio River Trail – Cincinnati Flying Pig Statues loop from Salem Heights, a 59.7-mile path, includes a significant elevation gain of 2,259 feet, providing a challenging ride for those seeking more climbing.
Yes, many road cycling routes around Crestview are designed as loops, allowing you to start and end at the same point. Examples include the Roadbike loop from Fort Thomas, a 20.7-mile trail, and the Roadbike loop from Melbourne, which spans 32.7 miles.
For a moderate road bike ride, you have several excellent choices. The Cincinnati Flying Pig Statues loop from Riverbend Music Center is a popular 27.3-mile route with 469 feet of elevation gain. Another great option is the Wasson Way – Ault Park loop from Salem Heights, covering 21.3 miles with 1,151 feet of ascent.
There are over 15 road cycling routes available on komoot for the Crestview area, all categorized as moderate difficulty. These routes offer a variety of distances and elevation gains, catering to different preferences and fitness levels.
Beyond the dedicated road cycling routes, the region offers scenic paved trails. While a bit further south, the Timpoochee Trail (also known as the Scenic 30A bike path) is a well-known 18-mile paved recreational trail that winds along Florida's Scenic Highway 30A, offering stunning coastal views through charming beach communities and state parks.


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