The CHESSS Mission
  • To encourage development of suitable techniques, equipment and best practices for shorthanded sailing in the Chesapeake Bay and its environs.

  • To promote the growth of CHESSS throughout the Chesapeake Bay.

  • To promote shorthanded racing throughout the Chesapeake Bay and its environs.

  • To recognize the accomplishments of shorthanded sailors throughout the Chesapeake Bay.


Check out the new Resources section!

Click here or click on "Resources" in the toolbar at the top of the page for tips, educational articles, "local knowledge" and more!


We encourage everyone to install the RaceQs app on their smartphone and upload their tracks after races and Challenges.  It's fascinating and educational to watch the event play out.  Get it HERE



Event Schedule


5/11 (Sat) AYC Spring Oxford | Results here

5/18 (Sat) CHESSS Gather 'n Gab | Results here

7/27 (Sat) CHESSS Poplar Is. Fiasco | Register here

Poplar Island Fiasco NOR/SI | Download here

8/2  (Fri/Sat) SMCM Gov. Cup | Results here

8/17 (Sat) CRAB charity regatta|Results here

9/7  (Sat) NASS Fall Oxford| Abandoned

9/21 (Sat) AYC new Solomon's Race

9/27-28 (F/S) AYC DH Distance Race| Register here

10/5 (Sat) Race to Rock Hall

10/19 (Sat) BCYA Harbor Cup

*=Need confirmation from OA


Register for Challenges at: info@chbaysss.org.

June 15, 2019 – Classic Boat Festival St Michaels, (Father’s Day Weekend)

Wooden and fiberglass classics, vintage racers, and other antique and Chesapeake Bay-related boats are coming to the Chesapeake Bay Maritime Museum June 14–15, 2019 for the 32nd annual Antique & Classic Boat Festival and the Arts at Navy Point in St. Michaels, Md. Hosted by the Chesapeake Bay Chapter of the Antique & Classic Boat Society, this Father’s Day weekend event brings a sense of nostalgia to the Miles River and CBMM’s docks and campus, drawing some of the area’s finest classic boats, nautical and maritime treasures, entertainment, food, and libations to this waterfront festival.

Link to event info:  http://cbmm.org/event/antique-classic-boat-festival/

Rendezvous:  Thomas Point Light to St Michael’s
Start: 10:00 AM

July 13, 2019 – Sea Food Festival Tilghman Island

The Tilghman Island Volunteer Fire Department will hold its Crab Fest on Saturday, July 13, 2019.  It will be held at the fire department and adjacent Kronsburg Park on Main Street, Tilghman Island.

Live Music at noon, Crab Race, Queen Contest and Fireman’s Parade, Nautical Artisans and Craft Vendors.

Local Steamed Crabs – All You Can Eat and by the Dozen “Market Value,” Crab Cakes, Crab Nuggets, Stripped Clams, Steamed Shrimp, Chicken BBQ Dinner with Potato Salad, Baked Beans and Roll. Pit Beef, Hamburgers, Hot Dogs, French Fries, Cold Beer, Sodas, and Homemade Lemonade.

The event begins at 11 AM; admission is FREE, food items priced separately, 50/50 raffle.

Bring the whole family for a day filled with fun, sun and seafood.  All proceeds go to the Tilghman Volunteer Fire Department.

Link to event info:  https://tourtalbot.org/event/tilghman-island-day-festival/2019-07-20/

Rendezvous:  Thomas Point Light to Tilghman Island Watermen’s Museum
Start: 10:00 AM

August 10, 2019 – Waterman’s Appreciation Day & Crab,

On Sunday, August 11, 2019, the 10th annual Watermen’s Appreciation Day comes to the Chesapeake Bay Maritime Museum in St. Michaels, Md., featuring a spirited boat docking contest, steamed crabs and other regional food, live music, beer, boat rides, family activities, and more. The fundraising event is organized by CBMM in cooperation with the Talbot Watermen Association, with proceeds benefiting both organizations.

Beginning at noon, the event’s “watermen’s rodeo” boat docking contest returns to the Miles River near CBMM’s 1879 Hooper Strait Lighthouse. Bleacher seating will be provided for spectators to the contest


Rendezvous:  Annapolis to St Michael’s
Start: 10:00 AM

Member Recognition

Solo Spinnaker Tips

Click here for a great video on solo spinnaker handling.

Great attendance at the 2017 General Meeting!
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