ST MICHAELS
SIGNATURE EVENTS
Every Thursday night, St. Michaels transforms into a culinary celebration. Fifteen of the town’s best restaurants and chefs offer special prix fixe menus, chef-driven tastings, and curated pairings — making Thursday the new Friday.
Every Thursday Night
Reservations Recommended
Log canoe races are a historic Chesapeake Bay tradition featuring 19th-century wooden vessels racing on Maryland's Eastern Shore from June through September.
June-September
An evening rooted in the bounty of the Eastern Shore, Community Harvest Supper brings together a culinary alliance of St. Michaels' finest chefs and local farmers around one extraordinary table. The evening unfolds with a welcoming reception, family-style feast, silent and live auctions, live music, and dancing, all in celebration of the food, people, and community that make our region so special.
Sunday
September 20, 2026
3:00 pm
One of the nation’s largest gatherings of its kind, Mid-Atlantic Small Craft Festival XLII celebrates the craftsmanship and innovation showcased through these vessels during a family-friendly weekend defined by camaraderie, tradition & fun.
October 2-4, 2026
St. Michaels comes alive with scarecrows, pumpkins, Jack Russell races and cocktails. One of the most colorful times of the year to Experience St. Michaels.
October 17-18, 2026
Experience two hours of pure fun at the St. Michaels Jack Russell Races! Hosted on the St. Michaels Inn lawn, this high-energy event welcomes all dogs and humans. Whether racing or watching, every ticket supports a registered 501(c)(3) raising vital funds for local shelters like Talbot Humane, Baywater Animal Rescue, and Caroline County Humane Society.
St. Michaels Inn Lawn
October 18, 2026
Registration 9am
Races 11am
Celebrate the holiday season in downtown St. Michaels with a festive weekend of local shopping, seasonal dining specials, and holiday cheer along Talbot Street.
December 3–6, 2026
Thursday–Sunday | Downtown St. Michaels
Serving 39 Years of Community Service! The mission of Christmas in St. Michaels is to provide resources to help local non-profit groups enhance the quality of life for the residents of the Bay Hundred community.
December 10-13, 2026
