Favorite Weekend Cruise: Galesville, MD

For over 20 years now, three of my best friends and I have made a tradition of doing an annual sailing trip on the Chesapeake Bay with our dads. We “kids” are now grown up and dispersed around the globe, but our four dads still live within three miles of one another back home in Pennsylvania.
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For over 20 years now, three of my best friends and I have made a tradition of doing an annual sailing trip on the Chesapeake Bay with our dads. We “kids” are now grown up and dispersed around the globe—Adam is a pilot in the Air National Guard, Blake a financial guru and Jeremy works at a bank, while I am usually either delivering yachts or writing about them. But our four dads still live within three miles of one another back home in Pennsylvania.

This past summer we continued the tradition. We had two boats this time round, and sailed from Annapolis aboard Adam’s Tartan 37, Audentia, and my dad’s latest Sojourner, a 1986 Wauquiez Hood 38. The father-son duos split up between the boats, and we flew spinnakers around Thomas Point and headed for the West River and Galesville, which has become our go-to weekend spot when the wind is too light to warrant six hours of motoring to Baltimore. We sailed close enough to each other to toss sandwiches between the boats during lunch.

Galesville offers the perfect compromise. There is a choice of restaurants ashore, but the anchorage is isolated and picturesque enough to warrant cooking out as well. The eight of us climbed ashore at Pirate’s Cove Restaurant, but on seeing the white tablecloths we headed farther south to Thursday’s Steak & Crabhouse, where they sat us outside at a picnic table where we could get boisterous.

Galesville, on the southwest fork of the West River, is only a two-hour sail from Annapolis. Getting there takes you close to Thomas Point, the oldest screwpile lighthouse still in operation on the Chesapeake. One does not have to sail out around it, although leaving it to starboard when heading south is prudent. 

The West River is well marked, but can be tricky at night, as the channel snakes through a big S-turn and some of the daymarks are unlit. The channel is wide enough that you can sail into the anchorage, yet challenging enough to make it exciting, even on a typical light-air summer day. Missing a mark, as in most places on the bay, means grounding out in mud.

The Rhode River, which branches off to the west not long after you round the lighthouse, offers a myriad of quiet anchorages in any of its five adjoining creeks. (When we were younger, we used to water ski behind the dinghy here.) Galesville, only a short bike ride from Annapolis by land, may as well be on the moon. It’s more like a sleepy Eastern Shore town than its bustling Western Shore neighbor and has a distinct southern ambiance. Pirates Cove Marina and the historic Hartge Yacht Yard offer fantastic dock-walking opportunities, with loads of character boats to admire.

The main anchorage is east of Pirate’s Cove at the mouth of South Creek with good holding in mud. On weekends there may be other boats around, but there is another anchorage to the south in Smith Creek, which is sometimes less active. Outside of town, in the branches of the river, there are any number of quiet, private anchorages to enjoy. If you need to tie up, Pirate’s Cove Marina has transient slips and a fuel dock and is an easy side-to stop going in or out of town.

Galesville is close enough to most of the major destinations around the Bay Bridge area (Annapolis, Baltimore, St. Michaels) that it can be easy to overlook. It is so close to our home port, we ignored it for years until we realized it had exactly what we needed in a weekend cruise destination. 

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