St. Michaels Business Assoication | Support Local, Explore More Today

A marina with sailboats and motorboats docked near buildings, including a lighthouse and a red building, under a partly cloudy sky.

Photo Credit: Laura’s Focus Photography

Serving The Greater Bay Hundred Business Community

The St. Michaels Business Association is the proud voice of the businesses, shops, restaurants, and attractions that make St. Michaels one of the most beloved waterfront towns on the Chesapeake Bay.

We champion local commerce, connect our community, and celebrate the small-town charm that keeps visitors coming back season after season.

Events

Jun 1

Thursday Night Chef's’ Table Experience

Jun 1

Community Harvest Supper

Oct 16

Fall Into St. Michaels

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 pure fall magic woven into every corner of our historic waterfront town.

Oct 16

Yappy Hour at Foxy’s!

Kick off Fall Into St. Michaels with Yappy Hour at Foxy's Harbor Grille! Grab a drink, bring your pup, and settle in on Foxy’s patio to start the Eastern Shore's most spirited autumn celebration the right way.

Oct 16

Petals & Pumpkins Floral Arrangement Class

Petals & Pumpkins returns to Corah's Corner on Friday, October 16th from 6-9 PM under the pergola. Craft your own pumpkin flower centerpiece with fresh local blooms, sip three featured fall cocktails, and enjoy a cozy evening of fall fun with giveaways throughout the night. $60, family pricing available, space is limited.

Oct 17

Pumpkin Carving

Watch master carvers bring jack-o-lanterns to life at Pumpkin Carving, Saturday, October 17th at St. Luke's Parish Hall. Public viewing runs 9am-noon and 1-7pm (closed briefly for judging), with a chance to tour the finished themed creations and meet the carvers behind them.

Oct 17

Children’s Pumpkin Painting and Face Painting

Kids can paint their own pumpkin to take home and get their face painted at Children's Pumpkin Painting and Face Painting, Saturday, 11am-1pm at the St. Michaels Community Center. Free event, brought to you by the St. Michaels Police Department and SMYLE.

Oct 17

Pumpkin Baking Contest

Sample sweet pumpkin creations from local bakers at the Pumpkin Baking Contest, judging begins at 11am at the St. Michaels Community Center. Buy a slice or the whole pie, with proceeds benefiting the Community Center.