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.
Author:
Updated:
Original:
Galesville_1

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. 

Related

m123728_13_01_171012_PMA_02901_9999

Alicante Announced as an Ocean Race Europe Stop

The Ocean Race Europe, a new event in offshore sailing, will include Alicante as one of four stopover cities. This European offshoot of the former Volvo Ocean Race will include the biggest change to the racing rules under the new title—fully crewed IMOCA 60s will join the ...read more

01-LEAD-doublehanded2

Preparing for a Doublehanded Race

A few months ago we took a look at the development and attraction of doublehanded racing (Two to Tango, June/July 2020). Hopefully, that served to whet your appetite. If so, the question becomes: “How do I get started? The good news, as we explained in Part 1, is that if you are ...read more

01-LEAD-Day-three---dolphins.-300-dpi

A Key Approach to Passagemaking

How you approach offshore sailing is key to the success of each passage. In addition, some of the most valuable, even crucial attitudes and skills may not be either learned or valued in everyday life on shore and may even fly in the face of talents that are greatly admired and ...read more

OceanVoyagesInstitute-2048

Point of SAIL: Mary Crowley of the Ocean Voyages Institute

In this episode of Point of SAIL, Principal Editor Adam Cort talks with Mary Crowley, founder and executive director of the Ocean Voyages Institute, a not-for-profit based in California that has been both educating sailors and working to preserve the health of the world’s ocean ...read more

01-Ocean-Voyages-Institute_PHOTO-READY_1_pg

Tracking and Catching Plastic Waste

Plastic waste—in the form of everything from plastic soda bottles to abandoned fishing nets—constitutes a major threat to the health of the world’s oceans. Giving the immense size of an ocean, though, actually finding all the plastic floating around out there in a time-efficient ...read more

Dreramcatcher -Cate Brown

Marblehead to Halifax Canceled; Alternative Races Planned

The Marblehead to Halifax race that was scheduled for this summer has been canceled due to continuing Covid concerns. Organizers at the Boston Yacht Club and Royal Nova Scotia Yacht Squadron who co-sponsor the event have made the decision because of uncertainty about when the ...read more

SailGP-Team

SailGP Announces Roster and Coach Additions

Athletes Daniela Moroz, CJ Perez and Paul Campbell-James have been added to The United States’ SailGP lineup. Also joining the team will be head coach Philippe Presti. Moroz is a four-time Formula Kite World Champion and two-time U.S. Sailing Rolex Yachtswoman-of-the-Year. ...read more

NEW-westcoastmultihullsmob

Chartering the West Coast

Although two-thirds of the U.S. boating population lives along the Eastern Seaboard, there are many hardy and enthusiastic cruising sailors on the “left coast” as well. Better still, if you’re looking to charter on the Pacific side, there’s plenty of great sailing and many clubs ...read more