Vintage boats, coastal art and a weekend of history return to St. Michaels
Written by Kristen Hampshire
Photography by Bill Mish
More than a century of boating history will be docked and on display during the 38th annual Antique & Classic Boat Festival and Coastal Arts Fair, June 19-21, at the historic Chesapeake Bay Maritime Museum.
“We typically have well over 100 total boats, both in the water and on land,” says Kathy Jones, this year’s boat show chairperson. “It’s all-encompassing; the museum turns over the entire grounds to us, and we really take over the space.”
With its blend of heritage and hands-on experiences, repeat attendees consider the festival a must-go tradition. For newcomers, the event is often an unexpected discovery—a chance encounter with history along the waterfront.
“You never know what you’ll find,” Kathy says. “Some people come specifically for the show, and others just happen to be in St. Michaels and stumble upon it. Either way, there’s something here for everyone.”
A Floating Timeline
Each year, the show adopts a theme to spark interest and highlight a specific slice of boating history. For 2026, the focus is “Boats Built in Michigan & the Midwest,” showcasing iconic brands such as Chris-Craft, Century, Lyman and Gar Wood.
But the lineup goes beyond the expected. Larger, rarer vessels—including a 67-foot custom 1915 cruiser and a 1926 motor yacht—offer a glimpse into early 20th-century engineering and design.
From historic skiffs to mid-century runabouts and late classic-era cruisers, the range reflects decades of innovation across materials and styles, from wood to fiberglass and beyond. “We try to choose a theme that draws people in,” Kathy says. “They see it and think, ‘That’s interesting, let’s go see what these boats are all about.’”
More Than a Show
While the boats are the centerpiece, the experience extends well beyond the docks.
Free boat rides on Saturday and Sunday offer another hands-on introduction, giving guests a chance to see and feel these vessels in motion.
On land, the juried Coastal Arts Fair brings together regional artists and makers, alongside a nautical flea market, food vendors and family-friendly activities. Boating history talks, scheduled throughout Friday and Saturday, round out the weekend with deeper dives into restoration, craftsmanship and legacy brands.
“Everyone is here because they care about preserving these boats and sharing their knowledge,” Kathy says.
At its core, the festival is driven by a community of enthusiasts who share a deep appreciation for classic boats and the stories behind them. That passion spans generations and geographies, with participants traveling from across the Mid-Atlantic and beyond to attend. Some bring fully restored showpieces; others showcase boats still in progress, offering a behind-the-scenes look at the restoration process.
“It’s like-minded people who just have a passion for older boats,” Kathy says. “Once you get into it, you’re hooked!”
1915 Custom Cruiser (“MAR-SUE”)
A rare, large-scale vessel measuring 67 feet, this early 20th-century build offers a glimpse into the transition from houseboat to cruiser design.
1926 Red Bank Motor Yacht (“Foxglove”)
This striking wooden yacht reflects classic craftsmanship and the elegance of prewar motorboating.
1929 Custom Chesapeake-built Boat (“Iva W.”)
At 60 feet, this regional standout highlights local boat-building traditions and enduring Chesapeake Bay design.
1971 Egg Harbor Flush Deck (“Bird’s Nest”)
This 48-foot travel yacht represents mid-century innovation, blending performance with livable space.
Midwest Classics Collection
From Chris-Craft to Gar Wood, this year’s theme brings together iconic runabouts and cruisers that defined boating in Michigan and the Midwest.
Plan Your Visit
38th Antique & Classic Boat Festival & Coastal Arts Fair
Chesapeake Bay Maritime Museum
13 N. Talbot St., St. Michaels, MD
June 19-21 (Father’s Day weekend)
• Friday and Saturday: Full festival programming
• Sunday: Awards ceremony and final viewing
What You’ll See:
• 100+ antique and classic boats (on land and in the water)
• Featured theme: Boats Built in Michigan & the Midwest
• Rare vessels, including early 20th-century cruisers
Don’t Miss:
• Free vintage boat rides (Sat. and Sun., 1 to 3 p.m.)
• Boating history talks (Fri. and Sat., 11 a.m. to 3 p.m.)
• Juried Coastal Arts Fair and nautical flea market
Good To Know:
• Walk the full 18-acre waterfront campus
• Many boats are open for boarding
• Family-friendly with activities for all ages
Tickets & Info:
Visit the Chesapeake Bay Maritime Museum website (cbmm.org) for tickets and full schedule.
