ST MICHAELS
SIGNATURE EVENTS
Memorial Day Parade
Featuring over 50 exhibits including military and veteran groups, and classic cars! The parade is in remembrance of those who gave the ultimate sacrifice for our freedoms and values.
May 23, 2026
10:30-11:30am
Flag Day 2026 Events
The St. Michaels Parks and Recreation Advisory Board is proud to present Flag Day 2026 - a community-wide celebration running from June 6-14 in honor of our nations 250th anniversary.
Our main events will be centered around Flag Day, and we hope you will join us in making this a memorable and meaningful celebration for our entire town.
Clean Up and Dress Up the Town:
Saturday, June 6 | 8:00am - 12:00pm
Concert in the Park:
Thursday, June 11 | 6:00pm - 7:30pm
Parks and Poles History Walk:
Saturday, June 13 | 10:00am - 3:00pm
Picnic and Parade:
Sunday, June 14 | 10:00am - 5:00pm
Antique + Classic Boat Festival
One of the largest classic boat shows in the Mid-Atlantic region. Take a step back in time to celebrate the history and artistry of these venerable vessels with dozens of examples on land and in the water!
June 19-21, 2026
Log Canoe Races
Log canoe races are a historic Chesapeake Bay tradition featuring 19th-century wooden vessels racing on Maryland's Eastern Shore from June through September.
June-September
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
2026 St. Michaels Fireworks
Celebrating 250 Years of American History
Join the Town of St. Michaels as we celebrate 250 years of American history.
July 5, 2026
9:30-10:30pm
St. Michaels Fireworks + Big Band Night
St. Michaels harbor lights up the sky for this magical family friendly event. CBMM's host's Big Band Night to fill the air with sounds of days past.
July 5, 2026
Sunset
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.
Sept 5-7, 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
Fall into St. Michaels
St. Michaels comes alive with scarecrows, pumpkins, Jack Russell races and cocktails. One of the most colorful times of the year to Experience St. Michaels.
Oct 17-18, 2026
Midnight Madness
Sharing what's new and exciting coming this year. Stay tuned.
December 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
