Summary: The Chesapeake Bay Maritime Museum (CBMM) in St. Michaels is hosting its popular annual Charity Boat Auction on Saturday, September 5, 2026. The signature event brings dozens of donated powerboats, sailboats, and paddlecraft to the waterfront campus to be auctioned off to the highest bidder in support of museum education and restoration programs.
- Event Date & Auction: The live auction begins at 11:00 AM on Saturday, September 5, along CBMM's waterfront campus.
- Public Viewing Day: Prospective buyers can inspect the full fleet of donated powerboats, sailboats, tenders, and kayaks on Friday, September 4, from 10:00 AM to 6:00 PM.
- Auction Terms: Most vessels in the diverse fleet will be offered with no reserve.
Source: Chesapeake Bay Maritime Museum - Charity Boat Auction 2026
Summary: Rock Hall is hosting its annual Boaters Appreciation Day concert on Sunday, September 6, 2026, featuring a live Jimmy Buffett tribute at The Mainstay. The social gathering brings together visiting boaters, marina guests, and local mariners celebrating the conclusion of the peak summer cruising season.
- Concert Schedule: The live tribute performance kicks off at 4:30 PM on Sunday, September 6, at The Mainstay in downtown Rock Hall.
- Cruiser Gathering: Designed as a social thank-you to visiting boaters docked across Rock Hall Harbor, Swan Creek, and local yacht clubs.
Source: Rock Hall Maryland Official Events Calendar
Summary: Tickets and waitlists are open for CBMM's premier annual fundraising gala, "The Boating Party: Ode to the Oyster," taking place Saturday, September 12, 2026, along Fogg's Landing in St. Michaels. The social gala celebrates the relaunch of the historic 1920 buyboat Winnie Estelle following an extensive shipyard refit.
- Gala Schedule: Runs from 6:00 PM to 10:00 PM on Saturday, September 12, featuring a cocktail hour, waterfront dinner, drinks, dancing, and special programming.
- Cause & Relaunch: Proceeds support the relaunch of the historic buyboat Winnie Estelle as an on-the-water educational platform, alongside a refresh of the Oystering on the Chesapeake exhibit.
Source: Chesapeake Bay Maritime Museum - Boating Party Fundraising Gala
Summary: The prestigious 2026 St. Michaels Concours d'Elegance is taking place from September 25–27, 2026, hosted at the Kent Island Yacht Club on Eastern Neck / Chester, MD. The autumn social weekend combines historic motoring displays with dockside yachting gatherings along the Narrows.
- Yacht Club Venue: Hosted along the waterfront grounds of the Kent Island Yacht Club (117 Yacht Club Dr, Chester, MD).
- Featured Displays: Features a special class of classic pick-ups, the 100th Anniversary of the Springfield Rolls Royce, iconic Bentleys, and visiting luxury motor yachts.
Source: St. Michaels Concours d'Elegance at Kent Island Yacht Club
Summary: Organizers of the 2026 Annapolis Sailboat Show (October 15–18, 2026) have finalized a redesigned layout along City Dock to accommodate ongoing waterfront resiliency construction. The world's largest in-water sailboat show will bring over 150 vessels, 500 exhibitors, and expanded social venues to the Annapolis harbor.
- Social Venues & Floating Bars: The redesigned footprint includes four new bar locations integrated throughout the show piers, headlined by the new "No Wake Zone" floating lounge.
- Cruisers University: Educational masterclasses run October 12–16 at the Historic Inns of Annapolis, covering marine systems, diesel engines, and passage planning.
- Premiering Fleets: Showcases world and North American debuts, including the Knysna 550, Fountaine Pajot 48, Jeanneau Sun Odyssey 455, and Oyster 495.
Source: Annapolis Boat Shows - 2026 Sailboat Show Preview
Summary: The Maryland Department of Natural Resources (DNR) reminds recreational boaters that the mandatory August closure prohibiting all targeting and harvesting of striped bass will conclude on August 31, 2026. The targeting season officially reopens across all Maryland portions of the Chesapeake Bay on Tuesday, September 1.
- Reopening Date: Targeted striped bass fishing and catch-and-release resume legally across all Maryland Bay waters starting September 1, 2026.
- Fall Slot Limits: Boaters are reminded that standard fall rules apply upon reopening, requiring a 19-to-24-inch slot limit and a one-fish-per-person daily harvest limit.
Source: Maryland Department of Natural Resources Notices