Destinations · Maryland
Chestertown
MD · 39.2194, -76.0683
From Chestertown, Maryland, Byway's registries place 8 scenic byways within 30 miles.
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.
Day-trip loops
Baked loops for Chestertown are growing. The weave below 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
- Chestertown Station · 1 mi
- Buck Bacchus Store Museum · 1 mi
- Caulks Field Memorial · 7 mi
- Maryland's First Women Voters · 8 mi
- Conquest Beach · 9 mi
- Mitchell Bluff · 9 mi
- Kent Museum · 10 mi
- Crew's Landing · 10 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.
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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