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Chestertown Anchorage
✨ Hidden gem
Drop anchor on the Chester River right alongside one of Maryland's most beautifully preserved 18th-century towns — Chestertown's Georgian architecture and brick-lined streets are genuinely worth the trip ashore. The setting has a quiet, unhurried charm that's hard to find this close to the Bay, with independent shops, cafés, and the historic Washington College all within easy walking distance from where you tie up your dinghy.
Based on AIS data
quiet → busy
Marinas and anchorages near Chestertown Anchorage · times are dock to dock
Popular Times
Boats arriving and leaving, by local hour — the hours the quay is actually working.
00:0006:0012:0018:0023:00
Mon
Tue
Wed
Thu
Fri
Sat
Sun
- Busiest on Saturdays and Sundays
- Busiest around 07:00 — mostly boats leaving
- Half the boats that stop here have arrived by 14:00
- 85% of visits are overnight
- Typical stay: ~21h
Plan a Passage
Popular
16 legs boats have actually been recorded sailing.
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