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
- approx. 111 km (69 mi)
- Driving
- 1 h 14 min
- Suggested days
- 3
- Stops
- 9
- States
- MD
- Best time to go
- May and September–October
- Tolls and vignettes
- None expected
- 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. Best time to go: May and September–October. No toll roads expected for a car.
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Photos along the route
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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.
Which stops are on Chesapeake Bay?
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.
How do you drive Chesapeake Bay in 3 days?
3 days, split by driving time. Campsites from OpenStreetMap: check opening dates before you go.
- Day 1: Annapolis → St. Michaels · 24 mi · 0 h 26 minOn the way: U.S. Naval Academy.Overnight nearby, for example: Camp Wright (14 mi).
- Day 2: St. Michaels → Oxford · 21 mi · 0 h 23 minOn the way: Chesapeake Bay Maritime Museum, Tilghman Island.Overnight nearby, for example: Madison Bay Campground, Marina, and Restaurant (13 mi); Tideland Park Campgrounds (16 mi).
- Day 3: Oxford → Harriet Tubman Underground Railroad Visitor Center · 24 mi · 0 h 25 minOn the way: Cambridge, Blackwater National Wildlife Refuge.Overnight nearby, for example: Roaring Point Waterfront Campground (18 mi); Madison Bay Campground, Marina, and Restaurant (6 mi).
When is the best time for Chesapeake Bay?
The most pleasant months are usually May and September–October. Still fine, with some compromises, in April and June. Cold, short days in January. July and August are the busiest months: book campsites early.
Estimate from long-term temperature averages, terrain and pass seasons
More routes for the best months
Practical guides for this route
Photo by Malivez on UnsplashDriving in the US: The Rules European Visitors Most Often Get Wrong at the Wheel
Photo by Aleksandr Dalakian on UnsplashFuel, Tolls and Distances: Practical US Driving Math for Motorhome and Camper Travelers
Photo by Tracy Zhang on UnsplashUS national parks: entry fees, passes and reservations in plain terms
Themes
Plan this route for your vehicle
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FAQs
How long is Chesapeake Bay: Annapolis to Blackwater?
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.
How many days do you need for Chesapeake Bay: Annapolis to Blackwater?
We suggest 3 days: about 1 h 14 min of driving, which leaves time for the stops.
Where does Chesapeake Bay: Annapolis to Blackwater start and end?
It starts in Annapolis and ends in Harriet Tubman Underground Railroad Visitor Center.
Which states does Chesapeake Bay: Annapolis to Blackwater pass through?
Maryland.
Where can you camp along Chesapeake Bay: Annapolis to Blackwater?
OpenStreetMap lists 19 campsites and motorhome stopovers within 19 mi of the stops on this route. For example: Roaring Point Waterfront Campground, Washington DC / Capitol KOA Holiday and Adventure Bound Washington DC.
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