Bike Shops
Headwind Cycle
30546 Prince William Street
Princess Anne, MD 21853
Phone: 443-235-7377 or 443-736-2444
Website | Facebook
Description: Repairs and sales.
Trails
Great Delmarva Bicycling Trail Maps
Description: Incorporating over 2,500 miles of roads through historic Delmarva past farmlands, cypress swamps, marshes and creeks to fishing villages, wildlife preserves and ocean shores. From Chesapeake City to Cape Charles and from the Chesapeake Bay to the Delaware Bay. For those who enjoy the landmarks of early American history, the natural charms of rural scenery and for those who appreciate wildlife in its many forms. The cycling guide is designed to serve the interests of cyclists of all levels of ability and experience. Maps are available in the Visitor Center, by email, or by calling 410-651-2968 or 800-851-9189.
Somerset's Terrapin Run Trail
Construction of the first section of the trail began in 2019 and was completed in 2021. Planning of the second section from Westover to mid point is in process. When completed, the trail will parallel Rt. 413 from Crisfield to Westover, along the former railroad bed. Perfect for Walking and Cycling.
Current Trailhead locations:
4053 Hinman Lane, Crisfield, MD 21817
28242 Crisfield - Marion Road, Marion, MD 21838
Somerset County Trail Mix
Website | Facebook
Description: Get outside in Somerset. The website features the places in county to hike, bike, walk, paddle and more. Visit the website for more information, or take it with you by downloading the app. Available on Google Play or App Store.
Princess Anne
Boxwood Gardens
Corner of Washington Street and Somerset Avenue
Princess Anne, MD 21853
Description: Take a light stroll through an early 19th Century, privately-owned garden, featuring native and exotic plants in an ornamental parterre arrangement. Planting started by the wife of General George Handy, who served during the War of 1812. Open to the public during daylight hours only.
All Areas
Walk Somerset
Facebook | Facebook Group
Connect with them on their Facebook page or on their Facebook group to learn about getting outside with scheduled walks or find a new walk partner. Learn about #Lifeat3MPH.
Special Events
Annual Skipjack Bike Tour
Deal Island - Chance Fire Company
10090 Deal Island Road
Deal Island, MD 21821
Facebook
Description: Held the Saturday after Labor Day, the Skipjack bike tour has rides in 15, 30, & 64 mile increments through some of the most beautiful landscapes on the Eastern Shore. T-shirts for all riders, rest stops, EMS available, SAG Wagon. Helmets required. Sponsored by the Deal Island - Chance Volunteer Fire Company. Applications can be found at their website.
Sea Gull Century
Website
Description: Sea Gull Century is a nationally acclaimed bicycling event, beginning and ending on the campus of Salisbury University, tours the picturesque Eastern Shore of Maryland and offers two routes: Assateague Century Tour (100 miles) and Princess Anne Metric Tour (65 miles).
Headwind Cycle
30546 Prince William Street
Princess Anne, MD 21853
Phone: 443-235-7377 or 443-736-2444
Website | Facebook
Description: Repairs and sales.
Trails
Great Delmarva Bicycling Trail Maps
Description: Incorporating over 2,500 miles of roads through historic Delmarva past farmlands, cypress swamps, marshes and creeks to fishing villages, wildlife preserves and ocean shores. From Chesapeake City to Cape Charles and from the Chesapeake Bay to the Delaware Bay. For those who enjoy the landmarks of early American history, the natural charms of rural scenery and for those who appreciate wildlife in its many forms. The cycling guide is designed to serve the interests of cyclists of all levels of ability and experience. Maps are available in the Visitor Center, by email, or by calling 410-651-2968 or 800-851-9189.
Somerset's Terrapin Run Trail
Construction of the first section of the trail began in 2019 and was completed in 2021. Planning of the second section from Westover to mid point is in process. When completed, the trail will parallel Rt. 413 from Crisfield to Westover, along the former railroad bed. Perfect for Walking and Cycling.
Current Trailhead locations:
4053 Hinman Lane, Crisfield, MD 21817
28242 Crisfield - Marion Road, Marion, MD 21838
Somerset County Trail Mix
Website | Facebook
Description: Get outside in Somerset. The website features the places in county to hike, bike, walk, paddle and more. Visit the website for more information, or take it with you by downloading the app. Available on Google Play or App Store.
Princess Anne
Boxwood Gardens
Corner of Washington Street and Somerset Avenue
Princess Anne, MD 21853
Description: Take a light stroll through an early 19th Century, privately-owned garden, featuring native and exotic plants in an ornamental parterre arrangement. Planting started by the wife of General George Handy, who served during the War of 1812. Open to the public during daylight hours only.
All Areas
Walk Somerset
Facebook | Facebook Group
Connect with them on their Facebook page or on their Facebook group to learn about getting outside with scheduled walks or find a new walk partner. Learn about #Lifeat3MPH.
Special Events
Annual Skipjack Bike Tour
Deal Island - Chance Fire Company
10090 Deal Island Road
Deal Island, MD 21821
Description: Held the Saturday after Labor Day, the Skipjack bike tour has rides in 15, 30, & 64 mile increments through some of the most beautiful landscapes on the Eastern Shore. T-shirts for all riders, rest stops, EMS available, SAG Wagon. Helmets required. Sponsored by the Deal Island - Chance Volunteer Fire Company. Applications can be found at their website.
Sea Gull Century
Website
Description: Sea Gull Century is a nationally acclaimed bicycling event, beginning and ending on the campus of Salisbury University, tours the picturesque Eastern Shore of Maryland and offers two routes: Assateague Century Tour (100 miles) and Princess Anne Metric Tour (65 miles).