2017 Events

April 8 - April 9, 2017

Eastern Shore Sea Glass & Coastal Arts Festival

Please join Ophiuroidea, located at 609 S. Talbot Street, for a celebration of the frosted sea glass treasures and coastal arts. Artisans will be on hand to showcase and sell their sea glass inspired jewelry, home decor and more will be on hand.


April 29 - April 30, 2017

Winefest at St. Michaels

Winefest at St. Michaels is unique amongst wine tasting events. WineFest at St. Michaels is a streetscape festival where hundreds of wines will be poured and available for purchase at pouring venues throughout the beautiful town of St. Michaels, MD.


May 20, 2017

St. Michaels Running Festival

The St. Michaels Running Festival, now in its 6th year, is one of the premier destination races in the Mid-Atlantic. Runners are treated to gorgeous water views, a quick mile past charming main street shops, and the flattest, fastest USATF half marathon in the region.


June 3, 2017

St. Michaels Brew Fest

Enjoy live music and great beer in beautiful downtown St. Michaels. Three walkable festival locations let you really see the town while sampling the best beers the region has to offer.



June 16 - June 18, 2017

Antique & Classic Boat Festival

The Chesapeake Chapter of the Antique & Classic Boat Society annual event, is the largest of its kind in the Mid-Atlantic region. Featured are more than 100 of the finest classic boats. Includes boatbuilding demonstrations, maritime vendors and juried artists. Featuring live music, food and more.


July 1, 2017

Fourth of July Fireworks/Big Band Night

Join us for an incredible fireworks display over St. Michaels Harbor, and dancing to the sounds of the 30’s and 40’s at Big Band Night at Chesapeake Bay Maritime Museum on July 1st, followed by our annual Independence Day Parade & Ceremony on the 4th.  


July 17 - July 23, 2017

13th Annual Plein Air Easton

Plein Air Easton is the largest and most prestigious juried plein air painting competition in the United States. We invite you to experience the vibrancy and artistic excellence of Plein Air Easton and to be a part of the history being made here.


September 24, 2017

St. Michaels Concours d'Elegance

"An old fashioned garden party" along the picturesque waterfront lawn of the Inn at Perry Cabin. Join us for a day of casual elegance, Senior Award winning Automobiles, food, refreshment, and celebration.


October 7 - 8, 2017

Mid-Atlantic Small Craft Festival and Maritime Model Expo

Hundreds of amateur and professional boatbuilders, model boatbuilders, and enthusiasts come from all over the region to display their one-of-a-kind kayaks, canoes, and other traditional small craft, along with a variety of maritime models also on display and underway.


October, 2017

Fall Into St. Michaels

Experience the beauty of St. Michaels in the Fall! Wonderful shopping, dining and sightseeing in the crisp, clear autumn weather.


October 2017

Chesapeake Film Festival

Building on a legacy of diversity and quality, Chesapeake Film Festival’s 9th annual program will sharpen its focus on stories of particular interest and care to our region and community. Join the Discovery and share your interests!


October 28, 2017


Featuring live music, oysters and other local fare, an oyster stew competition, boat rides, retriever demonstrations, along with children’s activities, oystering demonstrations, harvesting displays and more.


November 10- 12, 2017

Waterfowl Festival

For over 40 years, the Waterfowl Festival has been dedicated to wildlife conservation, the promotion of wildlife art, and the celebration of life on Maryland’s Eastern Shore. Join us for demonstrations, food, art, and more!


December 2, 2017

Midnight Madness

It's the 16th Annual Midnight Madness in St. Michaels! Great shops will be open until midnight with snacks and refreshments, and special sales all day and night. Enter for a chance to win raffle prizes valued at over $15,000 with every purchase from participating sponsors. Drawings start at 11:30pm and you must be present to win.


December 8 - December 10, 2017

Christmas in St. Michaels

Christmas in St. Michaels is held annually the second weekend in December in historic St. Michaels, Maryland. Ticketed and free events including the Tour of Homes, Holiday Gala, Breakfast with Santa and largest Holiday Parade on the Eastern Shore have celebrated the arrival of the Christmas season for 30 years.