ST MICHAELS
SIGNATURE EVENTS
ChocolateFest
The 8th Annual St. Michaels ChocolateFest returns on Saturday, March 7, 2026, inviting chocolate lovers from near and far to savor an unforgettable day of decadent delights.
March 7, 2026
Sea Glass + Coastal Art Festival
A fantastic lineup of more than 60 exhibitors from across the country, great food and drinks, live music on two stages, and more.
April 18-19, 2026
November 21, 2026
Wine Fest
Featuring vineyards from North and South America, France, Germany, Italy, Spain, Portugal, South Africa, Australia, New Zealand, Bulgaria, and Austria—with more regions to be added.
April 25+26, 2026
Antique + Classic Boat Festival
One of the largest classic boat shows in the Mid-Atlantic region. This year’s theme of “Boats in Movies and Television,” a variety of sport boats that have memorably been featured on screen will be on display throughout the weekend.
June 19-21, 2026
4th of July Parade
The Children’s Parade will kick off the celebration on July 4th, beginning at 10:00am. All children, residents or visitors, are welcome to participate. Patriotic dress is encouraged for kids, bicycles, tricycles, wagons & pets!
July 4, 2026
Waterman's Appreciation Day
Get ready to experience the vibrant spirit of the Eastern Shore at Watermen’s Appreciation Day, hosted by the Chesapeake Bay Maritime Museum on Sunday, Aug. 9, from 10am-4pm.
August 9, 2026
Charity Boat Auction
A Labor Day weekend staple for more than two decades, the Charity Boat Auction is the flagship event of CBMM’s Charity Boat Donation Program, which accepts and sells gently used boats year-round.
September 5, 2026
St Lukes Art League Art Show
Not to be missed is the annual outdoor Labor Day Art Show Under the Tent front and center on Talbot St. where visitors can peruse over 300 original paintings by art league member artists.
August 2026
Mid Atlantic Small Craft Festival
One of the nation’s largest gatherings of its kind, Mid-Atlantic Small Craft Festival XLII celebrates the craftsmanship and innovation showcased through these vessels during a family-friendly weekend defined by camaraderie, tradition & fun.
October 2-4, 2026
Midnight Madness
Enjoy the brand-new Christmas Cocktail Crawl, festive live music, photo ops, and an After Party throughout town where non-winning tickets turn into exclusive shopping and dining discounts. Stay late. Shop local.
December 5, 2026
Christmas in
St Michaels
Serving 39 Years of Community Service! The mission of Christmas in St. Michaels is to provide resources to help local non-profit groups enhance the quality of life for the residents of the Bay Hundred community.
December 11-13
