In and Around the 2026 Annapolis Sailboat Show

Whether you’re here to check out the latest decked-out daysailers or just soaking in the Chesapeake Bay vibes, there’s plenty happening in the show and all around it. Local businesses are rolling out the red carpet with exclusive offers, and our exhibitors have packed the schedule with demos, pop-ups, and events you won’t want to miss. This is your go-to guide for making the most of your show weekend—from dockside to downtown.

Special Offers Just Outside the Show Gates

Federal House

During the show (Oct. 15-18), Federal House will open at 10 a.m. and serve brunch until 1 p.m. each day.

Boat Show Block Party

On the opening day of the show (Oct. 15), there will be a boat show block party along Market Street. Enjoy live music, outdoor seating, and special menu offers from Federal House, Iron Rooster, McGarvey’s, Middleton Tavern, and the Annapolis Market House. The festivities are set to start at 5 PM but they’ll be offering boat show exclusive deals all day long!

Optimist Club

The Optimist Club will be offering breakfast sandwiches, burgers, crab cakes, and nutty buddies just outside the show gates beside the Guardians of the First Amendment Memorial on Compromise Street. Proceeds go to supporting the club’s various community outreach programs.

Cool Opportunities Inside the Show

EWE Spirit Scavenger Hunt

Scavenger hunt cards will be handed out at the SpinSheet booth. Completed cards can be exchanged for stickers and temporary tattoos.

Dockside Ducks

Young sailors are invited to search the docks for hidden rubber ducks. They can be taken to a ticket or information and redeemed for a fun prize. Thet get to keep the duck too!

US Sailing Scavenger Hunt

Stop by the US Sailing booth to take part in a scavenger hunt for folks of all ages.

Mimosa Sunday

Sunday, October 18 | Attendees are invited to the No Wake Zone from 10 a.m. to 2 p.m. to enjoy a free mimosa courtesy of Cane Mixers.

SV Delos

Sunday, October 18 | SV Delos will be doing a meet and greet from 11 a.m. to 12 p.m. at the Quantum booth.