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Routes
Road cycling routes
United States
Maryland
Worcester County

Ocean Pines

The best road cycling routes around Ocean Pines

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.

Best road cycling routes around Ocean Pines

  • The most popular road cycling route is…

Last updated: July 8, 2026

63

riders

#1.

Delaware Bicycle Route 1

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…

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Moderate

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…

Easy
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Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

5.0

(1)

6

riders

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,…

Moderate

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate
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Popular around Ocean Pines

Hiking around Ocean Pines

Running Trails around Ocean Pines

Cycling around Ocean Pines

Tips from the Community

atemoche
April 20, 2025, Ocean City Beach

Fun riding the boardwalk and the alleys.

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kypriano
October 15, 2023, Assateaque Island

Watch out for the wild horses and the big horseflies.

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The Verrazzano-Narrows Bridge is a two-story suspension bridge that connects the New York boroughs of Staten Island and Brooklyn across The Narrows.

Translated by Google

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Amy
September 14, 2022, Assawoman Bay

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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Amy
September 14, 2022, Bethany Beach Boardwalk

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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Amy
September 14, 2022, Fenwick Island State Park

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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Amy
September 13, 2022, Calvin B. Taylor House

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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Frequently Asked Questions

What is the general terrain and elevation like for road cycling around Ocean Pines?

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.

Are there any easy road cycling routes suitable for beginners or families in Ocean Pines?

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.

What kind of natural features and landscapes can I expect to see along the road cycling routes?

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.

Are there any notable landmarks or attractions along the road cycling routes near Ocean Pines?

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.

Where can I park my car when planning a road cycling trip in Ocean Pines?

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.

What is the best season for road cycling in Ocean Pines?

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.

Are there any loop road cycling routes available in Ocean Pines?

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.

What do other road cyclists enjoy most about road cycling in Ocean Pines?

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.

Are there any road cycling routes that pass through charming towns or offer a glimpse of local life?

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.

Are there any specific permits required for cycling on trails or roads in the Ocean Pines area?

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.

Can I find cafes or restaurants near the road cycling routes in Ocean Pines?

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.

How many road cycling routes are available around Ocean Pines?

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.

Most popular routes around Ocean Pines

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