About 27 years ago, a group of sailors at Yankee Point Marina, off the Rappahannock River in Virginia, decided that a sailboat race in November would make a fine climax to the sailing season. Some of these sailors were approaching a mature age, and so were their boats, so they reckoned they would elevate their chances of getting into the trophies by placing an age restriction on the designs of the boats invited to participate. So began the Turkey Shoot Regatta, named for its proximity to Thanksgiving, for any sailboat built to a design that was at least 25 years old. A boat still in wet paint from its builder qualified as long as its design qualified.

After a few years of marginal November weather, the regatta was moved up to the Columbus Day weekend in October, and it is now held over the first weekend in October so as not to conflict with the Annapolis sailboat show. This year’s regatta will be September 29, 30, and October 1, and the age qualification for the boats’ designs has been lowered to 20 years — to allow those with newer older boats to take part.

As the only regatta of its kind at the time it was dreamed up, the Turkey Shoot attracted large numbers of participants, which led the organizers to believe that the event could possibly raise money for charity. Given the ages of some of the skippers, they chose the hospice support center that had recently been established on the Northern Neck (the peninsula between the Potomac River and the Rappahannock River, where the regatta is held). This year’s edition will be the 22nd Hospice Turkey Shoot Regatta. Over the past 21 years it has raised as much as $40,000 at a single event.

Cape Cory Typhoon in the 2015 Turkey Shoot regatta

Elizabeth Crowther (skipper), on the left, and Arabella Denvir winning the Cape Dory Typhoon class in the 2015 regatta

In 2013, the regatta moved to Carter Creek at Irvington, where the small town that boasted an opera house when steamboats were the commercial and cultural connection throughout the region offers a variety of shoreside facilities and distractions for regatta participants and their entourages. Rappahannock Yachts, a sponsor, hosts the shoreside activities in its yard under a large tent surrounded by good old boats (and a few newer ones), many of them being actively worked on. The adjacent Rappahannock River Yacht Club handles the race management, and a number of local organizations and businesses, including the Tides Inn with its marina, support the regatta.

Raising money for local hospice care providers (Hospice Services of the Northern Neck and Riverside Hospice Agencies) provides an extra enticement for sailors who like to sail for a good cause. The principal reward for participants in this race is fun — which is encouraged by the regatta’s format. The activities begin on Friday evening with a cocktail party under the tent followed by a skippers’ meeting. Breakfast is available on Saturday and Sunday, the regatta dinner is on Saturday, and prizes are given out Sunday afternoon.

Saturday’s race is a conventional class-start multi-leg course scored in the usual way. On Sunday, the race is a pursuit, where each boat is assigned a start time based on handicap and the first one across the finish line, whether it’s a Fisher 29 motorsailer or a tricked-out S2 7.9, gets the glory. Boats without a PHRF certificate will be assigned a handicap based on boats of similar design.

Boat speed isn’t everything; looks count too! Spectators aboard vessels following the races vote for the “Most Beautiful Boat,” and the winner receives a trophy identical to that of the overall regatta winner.

So…Chesapeake Bay good old boat sailors, and those passing though the Bay on the way south, take note. A weekend in the company of like minds and like boats is on offer. Carter Creek is a large sheltered anchorage and there’s time after the regatta to sail north to Annapolis for the sailboat show.

Details at turkeyshoot.org

Jeremy McGeary is the Good Old Boat senior editor, which is to say he’s the wizard behind the curtain responsible for much of what makes the magazine great.