4.8
(9)
180
riders
15
rides
Road cycling routes around Ocean Pines offer diverse scenery across Maryland's Eastern Shore. This planned community features over nine miles of waterfront property and 3,000 acres of wooded terrain. The region is characterized by coastal views, agricultural landscapes, and minimal elevation changes, providing accessible routes for various skill levels. Natural features include Assawoman Bay and Fenwick Island State Park, creating a picturesque setting for road cycling.
Last updated: July 8, 2026
63
riders
90.9km
03:25
30m
30m
This segment of Delaware Bicycle Route 1 offers a delightful road cycling experience, tracing the scenic coastal areas of southern Delaware. You'll pedal past the historic Fenwick Island Lighthouse, enjoy…
4.3
(4)
51
riders
41.8km
01:36
40m
40m
This easy road cycling route, the Fenwick Island State Park – Assawoman Bay loop, offers a delightful coastal spin. You'll pedal past the expansive Atlantic Ocean and then transition to…

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5.0
(1)
15
riders
46.6km
02:04
50m
50m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
5.0
(1)
6
riders
55.1km
02:04
60m
60m
The Roadbike loop from Luca's Pizza offers a wonderfully flat and accessible road cycling experience through Sussex County, Delaware. This 34.2-mile (55.1 km) route is perfect for a leisurely ride,…
7
riders
68.1km
02:46
70m
70m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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Popular around Ocean Pines
The Verrazzano-Narrows Bridge is a two-story suspension bridge that connects the New York boroughs of Staten Island and Brooklyn across The Narrows.
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This lagoon separates Ocean City and Delmarva. It's an incredibly peaceful place that's perfect for a picnic and wildlife spotting. You'll find long stretches of marsh grasses along the bay shores and pine woods. There are also heaps of birds!
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This is a peaceful place to breath in the salty ocean air and relax. Bethany Beach boasts golden sands, tax-free shopping and excellent restaurants. Bear in mind that you're only allowed to cycle along the boardwalk from 6 am to 9 am.
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This beautiful state park is found on the small strip of land between the Atlantic Ocean and Little Assawoman Bay – Fenwick Island. It's a great place for swimming and surfing, with showers, changing rooms and places to eat.
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This historic Federal-style home, built in 1832, is a museum of local history for Berlin town. The house has several exhibits with memorabilia connected to the town and its stories. For more information: https://www.taylorhousemuseum.org/
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There is nothing more beautiful than relaxing on the beach after a long walk and listening to the waves of the Atlantic Ocean crashing on the shoreline.
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Road cycling routes around Ocean Pines are generally characterized by minimal elevation changes, making them enjoyable for a wide range of riders. The terrain often features coastal views, agricultural scenery, and charming small towns, providing a picturesque backdrop for your ride.
Yes, Ocean Pines offers several easy road cycling routes. For instance, the Fenwick Island State Park – Assawoman Bay loop from Luca's Pizza is an easy 25.9-mile path, perfect for a relaxed ride. Another great option is the Fenwick Island State Park – Assawoman Bay loop from Sinepuxent Bay Wildlife Management Area, which is 25.6 miles and also considered easy.
The routes around Ocean Pines offer diverse natural beauty. You'll encounter extensive waterfront property, wooded terrain, and coastal views of Assawoman Bay. Areas like Fenwick Island State Park and Assateague Island provide beautiful coastal landscapes, while other routes showcase farmlands and quaint towns.
Yes, while cycling, you might pass by or be near several interesting spots. For example, the region is close to the Fenwick Island Lighthouse. You can also find beautiful beaches like Ocean City Beach and the Sunset Island Waterfront, which are popular attractions in the wider area.
While specific parking areas for each route are not detailed, Ocean Pines is a well-equipped community. Many parks and public areas, such as Pintail Park and White Horse Park, offer parking facilities. When starting a route from a specific location like Luca's Pizza, parking is often available nearby.
Ocean Pines is enjoyable for road cycling across multiple seasons. The coastal environment means mild temperatures for much of the year. Spring and fall generally offer pleasant weather with fewer crowds, while summer provides warm conditions ideal for combining cycling with beach activities.
Yes, loop routes are a popular option in the area. The Fenwick Island State Park – Assawoman Bay loop from Luca's Pizza and the Fenwick Island State Park – Assawoman Bay loop from Sinepuxent Bay Wildlife Management Area are both excellent examples of scenic loop routes.
The road cycling routes in Ocean Pines are highly rated by the komoot community, with an average score of 4.75 stars. Cyclists often praise the diverse scenery, which includes coastal views and farmlands, as well as the generally flat terrain that makes for accessible and enjoyable rides.
Absolutely. The Delaware Bicycle Route 1, for example, is a moderate 56.5-mile route that provides coastal views, farmlands, and passes through quaint towns, offering a great way to experience the local charm.
Generally, no specific permits are required for road cycling on public roads and designated bike routes in the Ocean Pines area. However, if you plan to cycle within specific state parks or protected areas, it's always advisable to check their individual regulations for any entry fees or specific rules.
Ocean Pines and its surrounding areas, including nearby Ocean City, are well-equipped with amenities. You'll find various cafes, restaurants, and pubs, especially in the community centers and towns along or near the cycling routes, making it easy to refuel during your ride.
There are over 15 road cycling routes available around Ocean Pines, offering a variety of distances and difficulty levels to suit different preferences and abilities.


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