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
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.
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.
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.
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.
5: Layton’s Chance Winery
Take an easy ride on country roads through farmland surrounding Layton’s Chance Winery, then treat yourself to some wine! See the route.
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.
Bring your own bicycle or rent one while you’re here from one of the following spots:
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.
• 2524 Key Wallace Dr., Cambridge (near Blackwater National Wildlife Refuge).
• Hyatt Regency Chesapeake Bay Resort, 100 Heron Blvd., Cambridge.
On the Rivet
Beach cruiser rentals
2833 Ocean Gateway East (Route 50), Cambridge
409 Muir St., Cambridge
Dorchester Visitor Center
2 Rose Hill Pl., Cambridge
Bike Sales and Repair
On the Rivet
2833 Ocean Gateway East, (Route 50), Cambridge, 410-221-9981
Blackwater National Wildlife Refuge Visitor Center
2145 Key Wallace Dr., Cambridge
The refuge’s visitor center offers a self-serve “fix-it station” with tools.
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.