1. Shaw Bay on the Wye River - This is a well-known and often overlooked anchorage near the entrance to the Wye River. It has deepwater access and plenty of space to pick a quiet part of the anchorage. This is also a great anchorage for raft ups with friends. You could spend a whole day exploring the nooks and crannies of the Wye River.
2. Cacaway Island in Langford Creek - Cacaway Island sits at the junction of the East and West Forks of Langford Creek off the Chester River. It is an ideal anchorage with protection from most wind directions.
3. Reed Creek off the Chester River - Reed Creek is a wonderful anchorage on a mostly uninhabited creek directly off the Chester River. Both Langford Creek and Reed Creek lay off of the Chester River. If you’re looking for a beautiful town to explore from water, motor or sail up to Chestertown for the day and anchor in one of these two great anchorages for the night.
4. San Domingo Creek off Broad Creek - San Domingo Creek is nestled behind a beautiful set of islands named the Hambelton Islands. The creek is well protected and offers access to a dinghy dock for St. Michaels, one of our favorite towns on the shore because of its historical significance, great restaurants, local shops and the Chesapeake Bay Maritime Museum.
5. Bolingbroke Creek off the Choptank River - Bolingbroke Creek is located near the City of Cambridge on the Choptank River. This wonderful anchorage offers seclusion and protection while allowing for easy exploration of the City of Cambridge by dinghy. Cambridge is another one of our favorite towns on the shore. Unassuming, this historic town located on the Choptank is a great walking town with note-worthy restaurants and a hip undertone.