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Photo by Vicki Lathom
Photo by Vicki Lathom

Chesapeake Sailing Starts with a Bang

Ladies and gentlemen, get ready to start your engines. Or, hoist your sails. Just around the corner is Memorial Day weekend, the unofficial launch of the Chesapeake Bay boating season. And the unofficial focus of this seasonal event is the charming little resort town of St. Michaels on the eastern shore.

St. Michaels is a harbor port with a colonial past dating back to the mid-1600s. What was a place of ship building and seafood processing has now become a tourism treasure. It was ranked in USA Today’s 2015 Top Ten Best Coastal Small Towns.

Each year, the town hosts a three-day weekend for a critical mass of boats to the Miles River area with options for anchoring in the Wye River, Tilghman or Leeds Creek, in addition to St. Michaels’ harbor where the action is. With a combination of recreational boaters, racers and just plain tourists, St. Michaels sees thousands of visitors this weekend.

The sailboat race to St. Michaels is quite a spectacle. Hosted by the Miles River Yacht Club, one-design, PHRF and multihull fleets knock the cobwebs off with this first distance race of the season.

The Chesapeake Multihull Association and the Alberg-30 One-Design Association also use this race as a cruising event, sailing over on Friday to get prime real estate to greet racers as they cross the line. MRYC hosts one of the best race parties on the bay although, if you happen to be a racer, you better be able to drag yourself out of the bunk in the morning.

Many boaters plan their own rendezvous and activities for that weekend which involve various itineraries for the area. Some raft up a night in the quiet meandering Wye River and then another night in an equally quiet Leeds Creek just across from St. Michaels.

Anchoring in the harbor is a tight squeeze; with so many boats they reach out into the river.  Fortunately, a water taxi is at any boater’s fingertips by calling channel 71. Higgins Yacht Yard, St. Michaels Harbour Inn, St. Michaels Marina, as well as the members-only Chesapeake Bay Maritime Museum offer transient slips, but be sure to make a reservation.

For a tiny waterfront town, you can’t beat the options for eating out. Of course the local favorite the Crab Claw restaurant is front and center for Maryland crabs and seafood and has been so for 50 years. Located on an extension of the harbor, The Inn at Perry Cabin is where you go for luxury.

Ringing the harbor and its views are:  Foxy’s Harbor Grill for burgers, Town Dock Restaurant, St. Michaels Harbour Inn, St. Michaels Crab and Steak House, and Harborside Grill — all with outside seating.

On the main street there is another old standby, the Carpenter Street Saloon, which can’t be beat for breakfast. Go there on Sunday morning and you’ll see a large table of Albergers, who are celebrating the association’s 50th anniversary. Also in town on Talbot Street are:  Avis Pizzeria for gourmet pizza, Marcoritaville Tiki Bar and Grill,  Mike and Eric’s Front Street Restaurant, Bistro St. Michaels for classic Parisian dishes and the 208 Talbot Restaurant for fine dining in a rustic tavern atmosphere.

The 18-acre campus of the Chesapeake Bay Maritime Museum is a gateway to the harbor with the Hooper Strait Lighthouse standing like a sentry to the town.  It’s open for tours of the lighthouse and viewing of exhibits of small, working boats.

Saturday, the Museum is sponsoring a Party on the Point, transforming into a waterfront festival to celebrate its 50th anniversary with music, food, drink and craft vendors. The Patriot will take out visitors every evening for cocktail cruises, and the Crab Claw Restaurant next door, which is also celebrating 50 years, is putting on a  Friday night party with 60s music.

For tourists, St. Michaels even has a winery within downtown walking distance, with tasting room hours every afternoon.  Downtown has a Graul’s supermarket, which also sells wine and beer.

One of my favorite, somewhat evil pursuits is to get to the harbor anchorage early and then watch the others come in and try to find space, sometimes with a bit of waving off by other boaters. I’ve seen boats anchor over and over again, trying to find holding ground.  You also get to see the range of boating experience when someone throws an anchor over that isn’t attached to the boat.  The look on the crew’s faces is over the top.

For cruisers who prefer a less adrenaline-driven experience, Leeds Creek across from St. Michaels is peaceful and it’s possible to dinghy over the St Michaels.

Joining the unofficial Memorial Day fleet to the Miles River is a must-do. There is electricity in the air – all those white sails crossing over, interspersed with power boats, all skippers knowing that across the Bay and around the bend there is a party of a sort you rarely get to attend.

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