If you’re looking for the perfect way to spend Father’s Day weekend on Maryland’s Eastern Shore, the 38th Antique & Classic Boat Festival and Coastal Arts Fair at the Chesapeake Bay Maritime Museum is a must-visit event.
From June 19–21, visitors can enjoy one of the Mid-Atlantic’s largest gatherings of antique and classic boats while experiencing the charm, history, and waterfront lifestyle that make St. Michaels such a special place to call home.
Hosted by the Chesapeake Bay Chapter of the Antique & Classic Boat Society, this beloved annual tradition transforms the Chesapeake Bay Maritime Museum campus into a vibrant celebration of craftsmanship, boating heritage, and coastal living along the scenic Miles River.
A Weekend Full of Maritime Charm
The festival runs Friday and Saturday from 10 a.m. to 5 p.m. and Sunday from 10 a.m. to 3 p.m., offering three days packed with activities for all ages.
This year’s theme, “Boats Built in Michigan & the Midwest,” will showcase iconic vintage vessels from legendary makers including Chris-Craft, Century, Lyman, Larson, Gar Wood, and Matthews. Guests can explore beautifully restored wood, fiberglass, and metal boats spanning generations of boating history—from historic vessels dating before 1918 to contemporary handcrafted wooden boats.
Whether you’re a boating enthusiast, an art lover, or simply enjoy life by the water, there’s something for everyone.
Coastal Arts, Family Fun & Waterfront Experiences
In addition to the impressive boat displays, the festival also features a juried Coastal Arts Fair where regional artists and vendors will offer coastal-inspired artwork, jewelry, home décor, and unique gifts.
Families can enjoy:
- Children’s activities
- A nautical flea market
- “Field of Dreams” boat sales
- Educational boating history talks
- Complimentary classic boat rides on Saturday and Sunday
Guests can also experience the Chesapeake Bay from the water with narrated historical cruises on the Miles River or ticketed sails aboard the 1955 skipjack Rosie Parks.
And of course, regional food and beverage vendors will be onsite all weekend serving local favorites.
Why Events Like This Make the Eastern Shore So Special
One of the many reasons people fall in love with St. Michaels and Maryland’s Eastern Shore is the lifestyle. Events like the Antique & Classic Boat Festival bring together history, community, waterfront culture, and small-town charm in a way that’s hard to replicate anywhere else.
Living here means having access to year-round festivals, scenic waterfront views, boating opportunities, locally owned shops and restaurants, and a strong sense of community connection.
Whether you’re visiting for the weekend or considering making the Eastern Shore your permanent home, this festival offers a perfect glimpse into the relaxed coastal lifestyle that residents enjoy every day.
Plan Your Visit
Advance tickets are available online, and guests can save by purchasing early. Two-day ticket options are also available for both Friday–Saturday and Saturday–Sunday admission packages.
If you’re planning to attend, be sure to arrive early, explore the museum campus, and enjoy everything St. Michaels has to offer while you’re in town.
Thinking about buying or selling a home on Maryland’s Eastern Shore? I’d love to help you discover the waterfront communities, historic charm, and local lifestyle that make this area truly unique.
