• St. Michaels Festivals and Events

  • St. Michaels offers a variety of annual festivals and events all year long.   The festivals are kicked off in early April with the Eastern Shore Sea Glass and Coastal Arts Festival, followed by the highly anticipated WineFest at St. Michaels.  As Spring turns to Summer, the annual Bay Day, St. Michaels Running Festival and St. Michaels Brewfest are held.   Summer in St. Michaels means eating crabs, and the Waterman's Appreciation Day at the Chesapeake Bay Maritime Museum is a fun filled day with music and all you can eat crabs!

    As the season turns brisk, our thoughts turn towards the annual Fall into St. Michaels, a festival throughout the town celebrating with a parade, pumpkin carving and more.    October also brings Oysterfest, held at the Chesapeake Bay Maritime Museum.

    The start of the holiday season for St. Michaels is Midnight Madness, held annually on the first Saturday.   The streets light up with festive cheer and the holiday season is celebrated all month long.   Christmas in St Michaels features home tours, for your chance to take a peek into the many beautiful homes around St. Michaels, all dressed up for the holidays.

    After you've attended the festivals, it's the perfect time to stroll the historic streets, dine in our award winning restaurants, shop in the many unique boutiques and galleries and wind down in one of our many enchanting Inns and Bed & Breakfasts!

    Just a leisurely drive from Baltimore, Washington and Philadelphia, St. Michaels is an escape from the ordinary, where another world awaits... 


  • The following is a sampling of annual events held in St. Michaels. For details or updates on these events, visit their websites or visit our Calendar

  • January

    Fireside Warmth. Let us warm your spirits by continuing the holiday season with after Holiday Sales on Talbot Street.

    Celebrate a New Year in St. Michaels, and enjoy a relaxing start to your new year.



    St Michaels Valentine's Day

    Enjoy a romantic interlude on Valentine’s Day at a special lodging, topped off with a culinary restaurant experience.  Visit "Where to Stay" for Romance Packages all month long.



    St Patrick's Day - March 17th  Celebrate the Irish

    Carpenter street cart races st michaels st patricks day

    Change the winter blues to green by celebrating St. Patrick's Day and the start of Spring.
    Carpenter Street Cart Races.  Midnight. St. Patricks's Day. Talbot Street.



    Talbot Restaurant Week

    Talbot Restaurant Week

    The popular Talbot Restaurant Week launch party featured 25 restaurants and food businesses that offered generous samples, as well as a chance to interact with chefs and owners. Dishes ranged from escargot brulee and crab eclairs to jambalaya and salted caramel brownies.

    Book a reservation today and enjoy the best that Talbot restaurants have to offer!


    Eastern Shore Sea Glass & Coastal Arts Festival

    Eastern Shore Sea Glass and Coastal Arts Festival

    Eastern Shore Sea Glass and Coastal Arts Festival  

    Hosted by Ophiuroidea 609 S. Talbot St. hosts the annual event. Artisans from around the country selling their sea glass and coastal inspired jewelry, art, featuring music and fun for all. 410-745-8057   www.seaglassfestival.com


    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.  Winefest at St. Michaels is held during the last weekend of April.



    Bay Day

    A great day for families and friends of the Chesapeake Bay. Many free demonstrations, kids activities, live music and more! Bring the whole family!

    Hosted by Phillips Wharf Environmental Center


    St. Michaels Running Festival

    St. Michaels running festival  

    St. Michaels Running Festival it’s a fun, community spirited event benefiting the town of St. Michaels and its local businesses. The day will start with various races including a 1 mile fun walk, a 5K, a 10K and a 1⁄2 marathon.

    The races followed by an all day festival with food, vendors and live music. We welcome you all to join St. Michaels local businesses, organizations and food purveyors for a day of exercise, fun and entertainment. For race registration, accommodations and St. Michaels information please visit their website.



    St. Michaels Brewfest

    St Michaels BrewFest

    St. Michaels Brewfest is held the last Saturday in May.  Noon to 4 PM

    Featuring over 70 Craft Beers, Casks, Seasonals, Meet the Brewmasters. Held throughout three locations in the Heart of St. Michaels. 


    Concerts in the Park

    St Micahels Community Center

    (June - September) weather permitting

    Musicians perform on Thursdays from 6:30 pm - 8:00 pm  Concerts are held along the St. Michaels harbor at Muskrat Park.  For a list of musicians please visit the community center website.  Sponsored by the St. Michaels Community Center 410-745-6073


    Strawberry Festival & Arts and Craft Show

    Strawberry Festival St Michaels

    Eastern Shore’s BEST strawberries. 50 Artisans. Something for everyone. 

    Festival is located on the grounds of St. Luke’s United Methodist Church on Talbot Street.  410-745-2534

    Antique & Classic Boat Festival

     Antique and 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 mahogany and chrome classic boats. Includes boatbuilding demonstrations, maritime vendors and juried artists.   Featuring live music, food and more.

    Festival is held at the Chesapeake Bay Maritime Museum  every Father's Day weekend. 410-745-2916



    Independence Day Celebration

    St Michaels Fireworks

    Independence Day ceremony & parade. St. Mary’s Square and through town.

    FIREWORKS! St. Michaels Harbor.    Photo Courtesy of CBMM

    Big Band Night at Chesapeake Bay Maritime Museum

    Dance to the sounds of the 30’s and 40’s, outdoors. Food for sale or pack a picnic. 410-745-2916



    Summer Seafood Festival - Tilghman

     Tilghman Island festival

    Tilghman Island Summer Seafood celebration Food, music, contests, exhibits, boat rides. 410-886-2677



    Waterman's Appreciation Day at CBMM

     Waterman's Appreciation Day

    Watermen's Appreciation Day is held in the middle of August, is sponsored by The Talbot County Watermen's Association and the Chesapeake Bay Maritime Museum, this annual event is becoming a favorite event.   Meet Chesapeake watermen celebrating their heritage. Watch professionals in action at a Boat Docking Contest, the "waterman's rodeo" or take a chance in the silent auction, featuring local artwork. Eat your fill at our crab feast, or enjoy hot dogs and cold beer while listening to live music

    Special guests each year, see website for more information.  Held at the Chesapeake Bay Maritime Museum (CBMM). 410-745-2916     Photo Courtesy of CBMM



    Labor Day Charity Boat Auction

    Chesapeake bay Maritime museum

    Labor Day weekend! Boating experts and novices alike have the same opportunity to bid on the boat of their dreams during their annual Labor Day Charity Boat Auction! Offerings include everything from wooden rowing skiffs to classic sailboats and modern power cruisers. Chesapeake Bay Maritime Museum. 410-745-2916 

    Labor Day Weekend Art Show

    Annual Labor Day Art Show held by St. Michaels Art League . St. Luke’s Church, Talbot Street


    St. Michaels Concours d'Elegance

    The Annual  St. Michaels Concours d'Elegance will return to it's home, the Town of St. Michaels, Maryland.  The St. Michaels Classic Motor Museum will host the event and throughout St. Michaels.  The St. Michaels Concours d'Elegance features rare Pre-War Grand Classics.  The St. Michaels Classic Motor Museum will host the event and throughout St. Michaels. 

    Mark your calendar for a day of casual elegance, Senior Award winning Automobiles, food, refreshment, and celebration.  www.smcde.org



    St. Michaels FaithFest

     St. Michaels FaithFest, held annually the last weekend in September.  Featuring Church representatives, Christian bands, children's games, outreach, guest speaker, food and more!  The FaithFest is held at St. Luke's United Methodist Church.


    Columbus Day Celebration at Simpatico

    Columbus Day event at Simpatico      simpatico columbus celebration

    Simpatico, Italy’s Finest Annual Food and Wine Columbus Celebration during Columbus Day weekend.
    Tastings of over 50 Italian wines, Limoncello, Bellinis, foods and artisan cheeses from Simpatico. Fabulous food from local Italian restaurants along with food demonstrations and tastings from local chefs. 
     Visit with Columbus as he shares his stories of travel adventures! Come try your luck at bocce ball, Italian trivia contest with prizes, and vote for your favorite artist during our art competition while you listen to live Italian music.  

    Noon-6pm. Fee covers all, visit Simpatico website for more info and tickets or call 410-745-0345.

    Fall Into St. Michaels

     Fall into St Michaels

    Fall into St. Michaels includes weekend long activities throughout the town. Scarecrow Contest with local businesses and community partners. Pumpkin Festival including Pumpkin Carving and Pie Baking Contest, Children's activities, parade and more!

    Jack Russell Terrier Races held on Sundays during Fall into St. Michaels at the Inn at Perry Cabin by Belmond


    Tilghman Island Day - Tilghman

    Tilghman Island Day

    Tilghman Island Day 
    Tilghman Island, Home of Maryland Seafood. Featuring exhibits, music, food, arts & crafts, races, skipjack cruises. 410-886-2677

    Mid-Atlantic Small Craft Festival & Maritime Model Expo 

    Mid Atlantic Small Craft Festival

    Mid-Atlantic Small Craft Festival and Maritime Model Expo have combined for the 2015 season. One of the nation’s premier small craft events! Hundreds of amateur and professional boat builders and enthusiasts display their skiffs, kayaks and canoes. Take part in demonstrations and workshops, or simply chat with the owners and watch these one-of-a-kind vessels race.
    The festival brings a collection of small craft to the museum’s Miles River waterfront, along with live music, scenic river cruises, food, beverages, and more.   Sailing skiffs, rowing shells, kayaks, canoes, paddleboats, prams and other one-of-a-kind boats will be in the water and on land throughout the weekend. Many will be accompanied by owners sharing their boating knowledge and experiences with festival-goers.

     Maritime Model Expo

    The Model Guild of the Chesapeake Bay Maritime Museum (CBMM), the North American Steamboat Modeler’s Association (NASMA), and the Washington Ship Model Society are sponsoring the expo. In addition to the museum’s 12 exhibit buildings and 18-acre waterfront campus, the Maritime Model Expo offers pond demonstrations, model races, model exhibits, family activities, food, and more.

    Held at the Chesapeake Bay Maritime Museum. 410-745-2916 


    Critter Release Day- Tilghman

    Critter Release Day at Phillips Wharf Environmental Center(PWEC) on Tilghman Island, is an end-of-season celebration and an adventure for kids (young and old), where they can help carry the live specimens back to the bay!   The event marks the closing day of the season for the PWEC and it was time for the fish and horseshoe crabs that had been cared for and studied to go back into their habitat.   Event held end of October.  For more info call PWEC 410-886-9200



    OysterFest at Chesapeake Maritime Museum is a celebration of the Chesapeake Bay oyster with live music, great food, family activities, skipjack and buyboats rides, oyster aquaculture and restoration demonstrations.

    Oysterfest is held the last weekend in October at the Chesapeake Bay Maritime Museum. 410-745-2916   Photo courtesy of CBMM



    Midnight Madness
    Midnight Madness st michaels 

    Midnight Madness is an annual event held throughout the town of St. Michaels the first Saturday in December.  Shops open ‘til midnight, special sales, refreshments and prize drawings.  The Town will be festively decorated for the season, and Carolers stroll the streets. You may even meet Santa...
    Drawings start at 11:30pm and you must be there to win.


    Christmas in St. Michaels

    Christmas in St. Michaels  Christmas in St. Michaels is held annually the second weekend in December in historic St. Michaels, Maryland. For more than a quarter century, both 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.

    Proceeds from ticketed events and the sales of our very popular Collectors Ornaments have raised more than one million dollars to directly benefit local non-profit organizations in our community. We invite you to join with us as we welcome Santa, the Christmas spirit and the joy of giving. 410-745-0745 

  • Before You Visit:

  • St. Michaels, Tilghman and the Bay Hundred area have a wide range of lodging options to suit every taste and budget. Find the perfect place to fit your needs here.

  • Nothing says Chesapeake Bay like a steaming pile of locally caught Maryland blue crabs, and our restaurants are serving the Chesapeake Bay's bounty, from steamed crabs and crab cakes to sweet soft shell clams and fresh rockfish.  Find the perfect restaurant here.

  • St. Michaels offers shopping galore, with an eclectic range of shops, including jewelry, clothing and home decor, galleries and more!   Stop by one of the many tasting rooms, offering specialty foods and locally made libations. Find our unique shops here.

  • Whether you're an experienced kayaker, a day-tripping boater, a sailing novice, a history buff, an avid fisherman, or anyone else who yearns to spend some time on the water, you will find something to do in St. Michaels and Tilghman Island. It's time to get out on the water and enjoy the outdoors!  Find your boating options here.

  • Special thanks to William Wilhelm Photography, the Town of St. Michaels and the Chesapeake Bay Maritime Museum for the use of their photos.

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