Chestertown Historic District (Chestertown, Maryland)
Chestertown Historic District (Chestertown, Maryland). Photo: Acroterion, CC BY-SA 4.0, via Wikimedia Commons

Road trip guide

Chesapeake Country Scenic Byway: the drive, the stops and where to sleep

Distance
About 85 miles (137 km)
Time
1–2 days
Best time
May–October

Eastern Shore waterfront towns, crab shacks and farmland along the Chesapeake Bay. All-American Road, Maryland.

Open this route in XCRSN

Highlights

The route

  1. Chesapeake City, MD
  2. Chestertown, MD
  3. Stevensville, MD

Road trip tips

Open this route in XCRSN
XCRSN planner: plan the whole drive before you leave. Live corridor fuel, overnight stops, Apple and Google Maps export.

More planning help