Great Oak Landing, stop
Great Oak Landing, stop — photo 2
Great Oak Landing, stop — photo 3
Great Oak Landing, stop — photo 4
Great Oak Landing, stop — photo 5
Great Oak Landing, stop — photo 6
Great Oak Landing, stop — photo 7
1 / 7

Great Oak Landing

Great Oak Landing sits on the upper Chesapeake Bay near Chestertown, MD, where you can drop anchor and take in the relaxed, summer-camp-on-the-water vibe that makes this spot a regional favorite. Ashore, you'll find a full-service resort with a pool, restaurant, and working boatyard — the kind of setup that makes lingering here feel easy and worthwhile.

Based on AIS data

quiet → busy

Popular Times

How full it gets, by local hour — tallest when the most boats are here.

00:0006:0012:0018:0023:00
Mon
Tue
Wed
Thu
Fri
Sat
Sun
  • Busiest on Saturdays and Sundays
  • Fullest around 22:00, emptiest around 11:00
  • Half the boats arrive by 14:00
  • 83% of visits are overnight
  • Typical stay: ~30h · max recorded 28 boats
Details →

Plan a Passage

Popular

22 legs boats have actually been recorded sailing.