Half shell shucked oysters on a bed of ice

Want to Know the Most Exciting Fall Events in St. Michaels, MD?

There are so many exciting things about autumn in St. Michaels! This fair-weathered season boasts mild temperatures, breathtaking sights, and community-centric fall events in St. Michaels! Each year, locals and visitors alike flock to the Eastern Shore to welcome this season and celebrate the area’s maritime culture, fresh-catch cuisine, and more! Immerse yourself in our community when you add these autumn events to your St. Michaels, MD, itinerary. 

Top 3 Fall Events in St. Michaels, MD


Want to know a secret? OysterFest at the Chesapeake Bay Maritime Museum is our favorite fall event in St. Michaels. This popular fall festival features, you guessed it, oysters! Enjoy oysters fresh from the Chesapeake Bay cooked and served a variety of ways by local chefs. Learn the tricks of their craft at various cooking demonstrations! 

Enjoy local food vendors thanks to some of St. Michaels tastiest restaurants. Sip local libations, too, thanks to Lyon Distilling Company. This local distillery will be serving up thematic drinks like oyster shooters! As the slogan says, “Get ready to sip, slurp, and savor!” OysterFest will be on Saturday, Oct. 26, 2019. This event is rain or shine, so don’t make a backup plan! 

Fall into St. Michaels 

Get excited for OysterFest the weekend before at Fall into St. Michaels! This community favorite welcomes autumn with an entire weekend full of traditional fall festivities. On Saturday, Oct. 19, 2019, stop by the St. Michaels Community Center from 10:30 a.m. to 7:00 p.m. to vote for your favorite pumpkin pie and pumpkin-carving design! Taste to your heart’s content, then support our local artisans and purchase your favorite pie. 

You can also view pumpkins on Sunday from 10:00 a.m. to 2:00 p.m. Also on Sunday, Oct. 20, are the Jack Russell Races! This quirky activity features dog races across several categories. From purebred Jack Russells and Dachshunds to mixed-breeds known as “So Your Dog Thinks He’s A Jack” all dogs under 25 pounds are welcome to race. If you’re interested, you can register your dog here. May the best pooch win! 

Waterfowl Festival

Each November, the Waterfowl Festival comes to St. Michaels to celebrate the Eastern Shore’s culture and heritage. The main event is the World Waterfowl Calling Competiton. The best callers come to the Eastern Shore each year in pursuit of reigning in the final rounds! Other events feature water sports like the Diving Dogs Competition as well as art exhibitions. This annual event will take place this year from Thursday, Nov. 7, 2019, to Sunday, Nov. 10, 2019. Be sure to check the schedule of events to plan your trip to St. Michaels accordingly. 

Enjoy Autumn at Wades Point Inn on the Bay 

Take advantage of these fall events in St. Michaels, MD, then enjoy the simplicities of autumn at Wades Point Inn. Our St. Michaels, MD, bed and breakfast is partially surrounded by the Chesapeake Bay. Throw on your favorite sweater and make your way to the bayside to enjoy a slice of pie alongside the bay. Watch the sunset cast golden-hues over the sparkling waters. 

Then, cozy up in your guest room at Wades Point Inn. Consider the Peach Room in the 1819 Main House. This second-story room features a double bed, private bath, and partial water views. Check our availability and start planning your autumn getaway to St. Michaels!

Peach Room - Interior