Chesapeake Bay: Annapolis to Blackwater
Sailboats in Annapolis, watermen’s villages, a tiny river ferry and eagle-filled marshes on Maryland’s Eastern Shore.
- Distance
- 111 km (69 mi)
- Driving
- 1 h 14 min
- Suggested days
- 3
- Stops
- 9
- States
- MD
- Updated
- May 2, 2026
At a glance: 3-day road trip of about 111 km (69 mi) with 9 stops, from Annapolis to Harriet Tubman Underground Railroad Visitor Center. About 1 h 14 min of driving in total.
Route description
Annapolis, Maryland’s capital, is a sailing town of brick streets around the harbor and the U.S. Naval Academy. From there, US-50 crosses the Chesapeake Bay Bridge, over four miles long; it is tolled eastbound and can back up heavily on summer Fridays.
Turn off to St. Michaels on State Road 33 for the Chesapeake Bay Maritime Museum and its screwpile lighthouse, then continue to the end of the road at Tilghman Island, where skipjacks, the last working sailboats of the bay, are moored.
For Oxford, take the Oxford–Bellevue ferry, one of the oldest privately run ferries in the country, a short crossing of the Tred Avon River that runs in the warm months and takes only a few cars at a time. Then continue via Easton to Cambridge.
South of Cambridge, the Blackwater National Wildlife Refuge has a wildlife drive with bald eagles all year and huge flocks of waterfowl in winter. Next door, the Harriet Tubman Underground Railroad Visitor Center tells the story of the woman who escaped here and returned to lead others to freedom.
Stop-by-stop itinerary
In driving order. Distances are estimates between consecutive stops.
- 1Start
Annapolis
MD - 21 km
U.S. Naval Academy
HistoryAnnapolis, MDThe Navy’s college on the Severn River, with a chapel and John Paul Jones’ crypt. Visitors enter on foot with photo ID through the Gate 1 visitor center.
- 338 km
St. Michaels
MD - 40 km
Chesapeake Bay Maritime Museum
HistorySt. Michaels, MDA waterfront campus with a screwpile lighthouse, working boatyard and the largest collection of Chesapeake Bay boats.
- 516 km
Tilghman Island
MD - 618 km
Oxford
MD - 719 km
Cambridge
MD - 816 km
Blackwater National Wildlife Refuge
NatureCambridge, MDMarshes with one of the densest bald eagle populations on the East Coast and wintering ducks and geese. Drive the Wildlife Drive slowly with binoculars ready.
- 92 km
Harriet Tubman Underground Railroad Visitor Center
HistoryChurch Creek, MDA state and national park center in the landscape where Harriet Tubman was born into slavery; the start of a driving byway past related sites.
