ST. MICHAELS, MARYLAND — Fall Into St. Michaels is on the table again this October, with oysters, pumpkin baking, and a harbor beer garden among the food stops the St. Michaels Business Association has posted.
The association’s event page sets the weekend Friday, Oct. 16, 2026, at 9 a.m. through Sunday, Oct. 18, at 10 p.m., with no tickets required for the overall celebration. St. Michaels Tourism’s signature-events calendar lists the scarecrow, pumpkin, Jack Russell, and cocktail stretch as Oct. 17–18 and links toward the same association program — so the published listings vary by source.
Confirm hours and reservations with each venue before you go.
| Stop | When / notes (SMBA listing) |
|---|---|
| Yappy Hour | Friday, Oct. 16, 5–7 p.m. at Foxy’s Harbor Grille — bring a dog, grab a drink |
| Petals & Pumpkins floral workshop | Friday, Oct. 16, 6–9 p.m. at Corah’s Corner; $40 per pumpkin arrangement; reservations via Katelin Frase, 410-310-6457 |
| Pumpkin Baking Contest | Saturday, Oct. 17, St. Michaels Community Center; judging begins 11 a.m. — sample or buy slices/pies; proceeds to the Community Center |
| Foxy’s Second Annual Beer and Oyster Garden | Saturday, Oct. 17, noon–5 p.m. at Foxy’s Harbor Grille & Lu’s at the Marina — seasonal beers, cocktails, oysters |
Source: St. Michaels Business Association
Drawn from public records; drafted with AI and edited by Peter Gorman before publication.
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