# 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 tot

Source: https://camping-spirit.com/guides/b10-chesapeake-eastern-shore/

**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. 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 |
| Route | Annapolis → Harriet Tubman Underground Railroad Visitor Center |
| States | MD |
| Updated | May 2, 2026 |

## 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

1. **Annapolis** (MD)
2. **U.S. Naval Academy** (Annapolis, MD): The 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.
3. **St. Michaels** (MD)
4. **Chesapeake Bay Maritime Museum** (St. Michaels, MD): A waterfront campus with a screwpile lighthouse, working boatyard and the largest collection of Chesapeake Bay boats.
5. **Tilghman Island** (MD)
6. **Oxford** (MD)
7. **Cambridge** (MD)
8. **Blackwater National Wildlife Refuge** (Cambridge, MD): Marshes 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.
9. **Harriet Tubman Underground Railroad Visitor Center** (Church Creek, MD): A state and national park center in the landscape where Harriet Tubman was born into slavery; the start of a driving byway past related sites.