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Road cycling routes
United States
Maryland
Somerset County

Princess Anne

The best road cycling routes around Princess Anne

79

riders

7

rides

Road cycling routes around Princess Anne, Maryland, traverse the flat coastal plains of the Delmarva Peninsula. The region is characterized by low elevation gains, offering accessible cycling experiences through rural landscapes and forested areas. Routes often follow quiet country roads, providing views of agricultural fields and local waterways. The terrain is generally level, making it suitable for various fitness levels.

Best road cycling routes around Princess Anne

  • The most popular road cycling route is Backbone Hill – Costen House Museum…

Last updated: July 8, 2026

36

riders

#1.

Backbone Hill – Costen House Museum loop from Salisbury University

102km

04:14

130m

130m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

24

riders

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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

Hard

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

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

Moderate
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Tips from the Community

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 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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Excellent hike around Salisbury City Park & Zoo. Once you get into the heart of the park, you walk along the waterway: it is a very pleasant hike.

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Amy
August 24, 2022, Costen House Museum

Built shortly after the Civil War by Dr. Issac Costen, Costen House is a journey back in time. His family lived in the house for more than a century and today it serves as a museum. You can go on a tour of the house year-round for $5. Call 410-957-3110 to arrange your visit.

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This bridge is named for Giovanni da Verrazzano, an Italian (Florentine) explorer. He was the first European who explored the Atlantic coast of North America in 1524. He was in the service of King Francis I of France. The bridge was built in 1964.

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Frequently Asked Questions

How many road cycling routes are available around Princess Anne?

There are 7 road cycling routes documented on komoot for the Princess Anne area. These routes offer a variety of distances and difficulties, catering to different preferences.

What kind of terrain can I expect on road cycling routes near Princess Anne?

The road cycling routes around Princess Anne primarily traverse the flat coastal plains of the Delmarva Peninsula. You can expect low elevation gains, quiet country roads, and views of agricultural fields and occasional forested sections. The terrain is generally level, making it suitable for various fitness levels.

Are there easy road cycling routes suitable for beginners in Princess Anne?

Yes, there are easy road cycling routes available. For instance, the Chesapeake Forest loop from Princess Anne is an easy 19-mile (30.6 km) route, perfect for those looking for a less strenuous ride through the area's natural beauty.

Are there any challenging or advanced road cycling routes in the Princess Anne area?

For more advanced cyclists seeking longer distances, the Verrazano Bridge – Calvin B. Taylor House loop from Salisbury University is a challenging 101.8 miles (163.8 km) trail. This route leads through varied rural landscapes and is typically completed in about 7 hours 24 minutes.

What are some popular starting points or trailheads for road cycling in Princess Anne?

Many popular routes, such as the Backbone Hill – Costen House Museum loop and the Backbone Hill loop, start from Salisbury University, which is a common hub for cyclists in the region. Another option is the Salisbury Park & Ride for routes like the Salisbury Riverwalk loop.

Are there circular road cycling routes available around Princess Anne?

Yes, most of the road cycling routes in the Princess Anne area are designed as loops, allowing you to start and end at the same point. Examples include the Backbone Hill – Costen House Museum loop and the Chesapeake Forest loop.

What is the typical length and duration of road cycling routes in Princess Anne?

Route lengths vary significantly, from shorter rides like the 19-mile (30.6 km) Chesapeake Forest loop, which takes about 1 hour 11 minutes, to much longer excursions such as the 101.8-mile (163.8 km) Verrazano Bridge – Calvin B. Taylor House loop, which can take over 7 hours.

What is the best time of year for road cycling around Princess Anne?

Given the region's flat terrain and coastal climate, spring and fall generally offer the most pleasant conditions for road cycling, with milder temperatures and less humidity. Summer can be warm, but early mornings are often suitable. Winter can be chilly, but rideable days occur.

What kind of scenery or viewpoints can I expect along the road cycling routes?

Road cycling routes in Princess Anne offer views of the region's characteristic flat agricultural lands, quiet country roads, and occasional forested sections. You'll experience the rural charm of the Delmarva Peninsula, often with glimpses of local waterways and historic architecture in towns along the way.

What do other road cyclists enjoy the most about road cycling in Princess Anne?

The komoot community frequently praises the Princess Anne area for its quiet country roads and minimal elevation changes, making it ideal for long, steady rides. Cyclists appreciate the opportunity to explore rural landscapes and agricultural fields without significant climbs. Over 70 road cyclists have used komoot to explore these routes.

Are there any moderate-difficulty road cycling routes in the area?

Yes, several routes are rated as moderate. The Backbone Hill – Costen House Museum loop from Salisbury University is a popular moderate 63.1-mile (101.6 km) trail, and the Salisbury Riverwalk loop from Salisbury Park & Ride is another moderate option at 50.3 miles (80.9 km).

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