Fall into St. Michaels
Date: October 17-18, 2026
Calendar of Events 2026
Fall Into St. Michaels is the Eastern Shore's most spirited autumn celebration, a full weekend of seasonal fun, festive flavors, and small-town charm that makes October in St. Michaels something truly special. No tickets, no hassle, just fall magic woven into every corner of our historic waterfront town.
Friday, October 16
Yappy Hour at Foxy's Harbor Grille
5:00pm - 7:00pm Bring your pup and kick off the weekend with a libation.
Petals & Pumpkins Floral Arrangement Class
Corah's Corner | 6:00pm - 9:00pm Fun for the whole family. Create your own pumpkin-tastic centerpiece with local flowers to spice up your autumn table. Space is limited and reservations are recommended. Contact Katelin Frase, 410-310-6457. Workshop: $40 per pumpkin arrangement.
Saturday, October 17
Pumpkin Carving
St. Luke's Parish Hall Public viewing begins at 9:00am to watch carvers in action. Venue closes from noon to 1:00pm for judging, then reopens 1:00pm - 7:00pm. Every year, the carvers amaze us with their creations. Tour the collection of themed jack-o-lanterns and meet the carvers.
Children's Pumpkin Painting and Face Painting
St. Michaels Community Center | 11:00am - 1:00pm | Free Event Brought to you by the St. Michaels Police Department & SMYLE. Kids, bring your creativity! Paint your very own pumpkin to keep, and enjoy no shortage of fun with a face painter on the premises.
Pumpkin Baking Contest
St. Michaels Community Center | Judging begins at 11:00am A fall favorite, sample delicious pumpkin creations from local bakers. Buy a slice or the whole pie, with proceeds benefiting the St. Michaels Community Center.
Children's Storytelling
Book Hounds | 11:00am Kids, get in the spirit with Halloween-themed stories brought to you by your local independent bookstore.
Foxy's Second Annual Beer and Oyster Garden
Foxy's Harbor Grille & Lu's at the Marina | Noon - 5:00pm Enjoy a curated selection of seasonal beers, cocktails, and oysters prepared in many ways. A shore delight!
4th Annual Wag-O-Ween Costume Contest
Meet in the parking lot behind The Preppy Redneck | Noon - 3:00pm Get your pets gussied up in their favorite Halloween costume and stroll through St. Michaels for trick-or-treating! Costume prizes awarded. Entrance fee: $10, all proceeds benefit Talbot County Humane Society Contact KC Bridges for sponsorship opportunities.
Sunday, October 18
Pumpkin Viewing
St. Luke's Parish Hall | 9:00am - 2:00pm The viewing follows the Pumpkin Carving contest, once the carvers have finished their work and judging has wrapped up. Stop by to tour the collection of themed jack-o-lanterns on display and see this year's winning creations up close.
30th Annual Jack Russell Races
St. Michaels Inn | 9:30am - 12:30pm The St. Michaels Jack Russell Races are an annual event that is a blast for dogs, their owners, and onlookers alike. Packed with dogs big and small, the races support local charities including Talbot Humane, Baywater Animal Rescue, and Caroline County Humane Society.
Stay connected and by following the St. Michaels Business Association on Facebook.