Destinations · Maryland
Chestertown
MD · 39.2194, -76.0683
Chesapeake Country Scenic Byway and Harriet Tubman Underground Railroad Byway are 2 of 8 signed byways within 30 miles of Chestertown, Maryland.
Understand
Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its attractions include a blend of past and present.
The same roads run past Kent Island, where they are ranked and described in full.
Day-trip loops
Ready-made loops for Chestertown are growing. What is within reach is measured today; plan a live day trip and the engine routes it now.
Within reach
Measured from Byway's own registries, 30 miles around town.
Scenic byways
- Chesapeake Country Scenic Byway · inside · national
- Harriet Tubman Underground Railroad Byway · 22 mi · national
- Lower Susquehanna Scenic Byway · 22 mi
- Horses and Hounds Scenic Byway · 23 mi
- National Historic Seaport · 27 mi
- Roots and Tides Byway · 28 mi
Lookouts
- Ma & Pa Trestle · 28 mi
- Loch Raven Dam · 29 mi
- Scenic Overlook · 30 mi
Named places
- George Washington · 0 mi
- Kirwan Meditation Garden · 0 mi
- Rolling Road Park · 0 mi
- Village At Chestertown Park · 1 mi
- Fountain Park · 1 mi
- Chestertown Historical Monuments · 1 mi
- Chestertown Historic District · 1 mi
- Chestertown Station · 1 mi
A day out of Chestertown, planned on real roads
The engine starts from town, weaves the byways and verified stops around it, and hands back an honest schedule — zero hallucinations.
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Take the scenic way to Chestertown.
Byway plans around your taste, verified places, real weather and opening hours — then opens every leg in Google Maps with one tap.
More day-trip bases nearby
- Rock Hall · 11 mi
- Edgewood · 19 mi
- Aberdeen · 21 mi
- Havre de Grace · 23 mi
- Kent Island · 23 mi
- Perryville · 24 mi