Fall into St. Michaels

Date: 2026 TBD

Get ready to FALL in love with St. Michaels this season!
Our charming town is turning into a festive autumn wonderland, and you won’t want to miss a single moment.

Here’s a taste of what’s waiting for you:

• Marvel at giant carved pumpkins glowing throughout town – and cast your vote for your favorite!

• Stroll through town and spot creative scarecrows crafted by local businesses.

• Bring your furry friends for Wag-O-Ween trick-or-treating AND Yappy Hour at Foxy’s!

• Follow the Martini Trail to sip seasonal creations and help crown the King of the Fall Martini!

• Savor the flavors at the Pumpkin Pie Contest where chefs and bakers compete for top honors.

• Don’t miss the always-hilarious Annual Jack Russell Races at St. Michaels Inn.

• Cheers to the season at the Fall Pumpkin Beer Garden at Foxy’s.

• …and SO much more all weekend long!

No tickets. No hassle. Just pure autumn magic.
Dine, sip, shop, and explore St. Michaels at its most colorful and cozy time of year.

Stay connected and by following the St. Michaels Business Association on Facebook.