2022: Top 5 Anchorages on Maryland’s Eastern Shore
(From North to South)
Chestertown's anchorage is on the southern side of the bridge with decent holding for large and smaller boats. Some patches of seaweed are on the bottom. This would be an ideal anchorage for fair weather forecasts but not ideal for high wind or cold fronts due to the fetch of the river. One of our favorite towns on the Eastern Shore, Chestertown is a beautiful historic town on the Chester River. A great walking town with restaurants, fresh bread shops, a theater, ice cream shop, markets, a playground and more. Chestertown is a college town so it becomes more alive at night when college is in and shops close earlier in the summer when college students are home. Be sure to visit the Sultana Education Foundation center on your way through town. If weather deteriorates, you can take a slip at Chestertown Marina. The boat ride up the Chester River to Chestertown is worth the trip itself- beautiful scenery, homes and wildlife.
Located on the West Fork of Langford Creek (off of the Chester River), Shipyard Creek is quiet and secluded. This anchorage offers good holding with protection from nearly all wind directions, with slight exposure to a southerly wind. Dinghy ashore at the Shipyard Boat Ramp but be aware that it can be shallow at low tide. Beautiful exploring via dinghy/kayak and smaller boat around Shipyard Creek and surrounding coves. If you like bird watching, this is your anchorage! Langford Creek is one of our favorite areas of the Chester River and all of the creeks off Langford never disappoint in natural beauty and wildlife. Stop by Cacaway Island on your way to or from the anchorage to explore a beautiful sandbar and beach.
Located off of the Wye River East, Pickering Creek is what one might call a “hurricane hole”. This is an isolated and protected anchorage from all wind directions. It's nestled among the forested banks of the Pickering Creek Audubon Center which offers outstanding views and hiking trails. Birds, fish and wildlife abound. Use caution at the entrance to Pickering Creek as it can be shallow when navigating in but opens up and gets deeper once inside. This anchorage will get muggy on a hot summer night but would be perfect for an autumn anchorage with a nice cool breeze. Navigating the Wye River to get to Pickering Creek is a treat in itself.
Located in the heart of St. Michaels, Fogg Cove is the place to anchor or moor if you want to be in the action. Fogg Cove is inside of St. Michaels Harbour, located just off of the Chesapeake Bay Maritime Museum and the Inn at Perry Cabin. You can dinghy into the historic town of St. Michaels or take the St. Michaels Harbour Shuttle. St. Michaels has it all- great restaurants that you can boat to, playgrounds for kids, beautiful streets to walk, markets and more. And don’t forget that you can use the ShoreRivers free pump-out boat on the Miles & Wye Rivers this service is offered mid-May through November 6th.
Located just off of Sherwood, Waterhole Cove is a quiet anchorage off of Harris Creek. This scenic anchorage is past Dun’s Cove on the left. It is exposed to the SE but provides adequate protection from other directions. Use the Sherwood public dock to walk around the streets of Sherwood. Lowes Wharf Marina Inn is a fun restaurant and bar, often with live music, that can be walked to in under 1 mile. Tilghman is about a 3 mile dinghy ride from Waterhole Cove and is another great place to stop by boat. It offers restaurants, fuel docks and a market. Waterhole Cove is a place to reset, enjoy nature and soak in the essence of life on Maryland’s Eastern Shore.
Click HERE for the 2021 Top Anchorages.
Click HERE for the 2020 Top Anchorages.
Click HERE for the 2019 Top Anchorages.
We encourage all boaters to continuously check the weather, local tides and charts of the area. Be sure to familiarize yourself in advance of arrival. (We pulled the Lat & Long coordinates in this list from Navionics. Be sure to navigate with caution and check your local charts and GPS.) Set your anchor with the appropriate scope ratio and turn on your anchor light at night if you are overnighting. You are responsible for your vessel and the safety of you and your crew. We also encourage everyone to practice environmental stewardship when they are cruising and anchoring. Leave no trash behind, pick up trash that you see and do not anchor is seabeds that have native sea grasses that are a habitat for our fisheries. Do not pump out your holding tank in the Bay and respect all wildlife. Most importantly, be safe and have a great time! Please do not hesitate to reach out to us if you have any further questions. We can be reached on VHF 16: Tow Jamm Marine or (410) 734-3000.*