Dorchester County on Maryland’s Eastern Shore is known for quiet roads, unspoiled landscapes and waterscapes, and wildlife. We are home to two IRONMAN triathlons. This is also the birthplace of Harriet Tubman of Underground Railroad fame. It all makes for wonderful cycling for riders of a range of abilities. So ride through nature, beauty, and history!  We have put together six suggested cycling routes of varying lengths throughout Dorchester in our Cycling Guide. See below for specifics on each of the routes or download the entire Dorchester Cycling Guide as a PDF or order a free hardcopy brochure. Try out a route or create your own! See a map that shows all six routes.

Dorchester Cycling Routes

Cycling | Visit Dorchester
1: Cambridge to Neck District

32 Miles Out and Back
Ride through small communities, farmland, a historic windmill, and enjoy great waterviews at the turn-around. See the route.

Cycling | Visit Dorchester

55+ Mile Loop
This is the course that IRONMAN triathletes have used for the bike portion of the IRONMAN 70.3 Eagleman race that happens in Dorchester each June. See the route.

Cycling | Visit Dorchester
3: Blackwater Wildlife Refuge

24 Miles Out and Back
Explore parts of the beautiful Blackwater National Wildlife Refuge, with 28,000+ acres of protected lands and great wildlife watching. See the route.

Cycling in Dorchester County on Maryland's Eastern Shore - Cambridge Waterfront | Visit Dorchester
4: Cambridge Waterfront

12 Miles Out and Back
Take in beautiful views of the Choptank River waterfront, a lighthouse, a marina, parks, and more. See the route.

Layton's Chance Winery in Dorchester County, Maryland | Visit Dorchester
5: Layton’s Chance Winery

10-Mile Loop
Take an easy ride on country roads through farmland surrounding Layton’s Chance Winery, then treat yourself to some wine! See the route.

Man Cycling | Visit Dorchester
6: Vienna to Elliotts Island

39 Miles Out and Back
Ride from a historic waterfront town through flat, open marshland with lots of waterviews. See the route.

Bike rental

Bring your own bicycle or rent one while you’re here from one of the following spots:

Blackwater Adventures
Offering bike rentals and guided tours. Bikes for adults and children available, as well as infant seats and pull-behinds.  If you’re staying at a vacation home, they can even deliver bikes to you.
Two locations:
• 2524 Key Wallace Dr., Cambridge (near Blackwater National Wildlife Refuge).
• Hyatt Regency Chesapeake Bay Resort, 100 Heron Blvd., Cambridge.

Dorchester Visitor Center
Cruiser rental (limited supply)
2 Rose Hill Pl., Cambridge

Bike Sales and Repair

Ready to Ride Pre-Owned and Vintage Bikes
Sales of secondhand and vintage bicycles.
1040 Hudson Rd., Cambridge, MD,  410-901-7556

Blackwater National Wildlife Refuge Visitor Center
2145 Key Wallace Dr., Cambridge, MD
The refuge’s visitor center offers a self-serve “fix-it station” with tools.

Cycling Events

Because of our flat roads and scenic landscapes, Dorchester County has become a popular location for endurance races, including two IRONMAN triathlons, cycling events, a cycling weekend for women, and more. See the list of upcoming endurance events.