• Effective May 17th St. Michaels lifts mask mandate. Read more here

  • The St. Michaels ChocolateFest and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts.   Our inns and bed and breakfasts will feature chocolate inspired get-away packages.   

     Join in the fun during The Galley's Chocolate Pie eating contest, there's something fun and tasty to do all weekend with other specials and events throughout town. 

    Chocolate lovers will enjoy strolling throughout the Town of St. Michaels to indulge in thousands of chocolate concoctions on Saturday, March 20th from 11:00 a.m. - 4:00 p.m. during the ChocolateFest Crawl, where participates will receive artisan chocolates, desserts and more.   ONLY Pre-Purchased tickets available.  


        The ChocolateFest Crawl is a rain or shine event.

  • 3rd Annual St. Michaels ChocolateFest Chocolate Crawl will take place on the first day of Spring on Saturday March 20, 2021.  The Chocolate Crawl will be slightly different this year.  We are asking venues to provide "to-go" tasting samples to enjoy outside (if the venue is located inside).  Masks must be worn indoors and in town due to Town of St. Michaels mandates.

     The Chocolate Crawl is SOLD OUT! NO DAY OF SALES!

    Available in quantities of 10 ( 1 ticket = $1) for $10
    One tasting per ticket
    Each ticket may be reimbursed during the Chocolate Crawl at participating CRAWL VENUES during the hours of 11 a.m. - 4 p.m. or until the chocolate runs out!

    Choose from thousands of amazing chocolate concoctions, desserts and candies at participating venues
    throughout the Town of St. Michaels.

    Pre-purchased tickets will be available for pick up starting at 9:00 a.m. at the ChocolateFest Crawl Pick-Up Area located on the corner of Railroad Avenue and Talbot Street at 100 S. Talbot Street.   


    Chocolate Crawl is a RAIN OR SHINE EVENT. 


    Tasting Venue Map Here. 



  • Chocolate Crawl Venues

     Saturday, March 20, 2021 11 am - 4 pm

    Aida's Victoriana Inn - 205 Cherry Street  Chocolate Fountain with pretzels, fruit and marshmallows - Cake Pops

    Ava's Pizzeria & Wine Bar - 409 S. Talbot Street  Vanilla Cheesecake Pops Dipped in Chocolate

    Awful Arthurs - 402 S. Talbot Street    Chocolate Covered Strawberries

    Blue Crab Coffee - 102 S. Fremont Street  Chocolate Caramels & Cherry Chocolate Brownies & Coconut Brownies

    DBS Fine Jewelers  - 308 S. Talbot Street   Chocolate Gemstones & Cake Pop

    Hambleton Inn Bed & Breakfast - 202 Cherry Street   Chocolate Chunk Cookies by Chef Patrick

    Hammy's Hideout -  209 S. Talbot Street  Caramel & Pretzel Chocolate Bark with Sea Salt

    Hopkins Original Art - 310 S. Talbot Street  Chocolate pretzel bags

    Limoncello - 200 S. Talbot Street   Fudge Nut Brownies 

    Olivin's - 110 N. Talbot Street   Dark pretzel toffee, sea salt caramel, carrot cake mini bars. Home made blood orange olive oil double chocolate sugar cookies.

    Ophiuroidea - 100 S. Talbot Street    Chesapeake Chocolate's crab shaped chocolate candy + coupon to use in store.

    Silver Linings - 203 S. Talbot Street  Chocolate stars with a special savings on each star 

    Simpatico, Italy's Finest - 104 Railroad Ave  Assorted Italian chocolates

    Skipjack's St. Michaels - 111 S. Talbot Street   Chocolate gelato

    Sprout - 114 S. Talbot Street  Cherry Chocolate and Rum Truffles, Chocolate Banana Bread, Dark Chocolate SPLATS (cocoa, pistachio, coconut and cherry), White Chocolate covered strawberry Brownies, Chocolate Babka

    St. Michaels Fine Woodworking & Cabinetry - 100 N. Talbot Street  Assorted Gourmet Chocolates

    The Galley - 305 S. Talbot Street   Chocolate cupcakes & Hot chocolate with peppermint schnapps 

    Theo's Steaks, Sides & Spirits - 407 S. Talbot Street  Dark Chocolate Mousse with Lyons Coffee Rum and Vanilla Whipped Cream

    The Preppy Redneck - 213 S. Talbot Street  

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  • Events Around Town


    Skipjack's St. Michaels   

    111 S. Talbot Street

    During ChocolateFest, Skipjack's will be hosting a Golden Ticket Scavenger Hunt! Golden Tickets will be hidden throughout Skipjack's St. Michaels store. Each Golden Ticket can be redeemed for a free item! Golden Ticket must be redeemed on same day as ChocolateFest - Saturday, March 20, 2021.




    104 Railroad Ave

    Simpatico Wine & Chocolate Tasting Venue  

    Join us for special paired Italian Wine & Chocolate tastings in our courtyard - a new "COVID-Safe" plan for this year for our ChocolateFest offering.

    In our efforts to limit contact and be as safe as we can this year within the COVID guidelines, we will again sponsor a Wine & Chocolate tasting event as part of the town wide ChocolateFest on Saturday March 20th from Noon to 5 PM. We will provide your tasting packages pre-poured with a fabulous selection of five (5) of our favorite Italian reds, whites or sweets paired with delectable Italian chocolates for you to enjoy seated in our courtyard at distanced tables for 5 seatings available on the hour from Noon to 4 PM, you choose the time when you purchase your tickets. Limited seating so purchase early!   NOTE: Once the number of tickets are sold for the seats available for the time slot to allow proper distancing of tables, then that time slot will be Sold Out. 

    Ticket can be purchased here


    The Galley  305 S. Talbot Street

    Save your appetite and get ready to be messy! The Galley will hold their 2nd Annual Chocolate Pie Eating contest during the St. Michaels Chocolatefest on Saturday, March 20th at 3:00pm.

    Kids and adults are welcome to participate. Winner will receive a $50 gift card to The Galley + bragging rights!

    Sign up early and reserve your spot.

    This will be a socially distanced event with all participants spaced out at appropriate distances. All COVID rules will apply.  More details here.

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  • Specials during ChocolateFest March 20, 2021

    Aida's Victorianna Inn -  205 Cherry Street

    Chocolate Truffles on bed on arrival.


    Awful Arthur's Seafood Company   402 S. Talbot Street

    Chocolate inspired food and drink specials


    Blue Crab Coffee   102 S. Fremont Street

    Chocolate Specials: Mexican Hot Chocolate Latte, Chocolate Espresso Bellini, Chocolate Baked Goods


    Carpenter Street Saloon  113 S.  Talbot Street

    Chocolate inspired cocktails


    Limoncello  200 S. Talbot Street

    Chocolate inspired cocktails


    Simpatico, Italy's Finest  104 Railroad Ave

    ChocolateFest Wine & Chocolate Tasting COVID Style Noon - 4pm

    In our efforts to limit contact and be as safe as we can this year within the COVID guidelines, Simpatico will host their Wine & Chocolate tasting event on Saturday March 20th. Tasting packages will be pre-poured with a fabulous selection of their favorite reds, whites or sweets paired with delectable Italian chocolates for you to enjoy seated in our courtyard at distanced tables for 5 seatings available on the hour from Noon to 4 PM, you choose the time when you purchase your tickets. Limited seating so purchase early! Details and tickets are here


    St. Michaels Inn   1228 S. Talbot Street


    The Galley  305 S.  Talbot Street

    Chocolate pie eating contest. Chocolate wine pairing dinner.


    Tilghman Island Inn -  Tilghman

    Book one night get second 50% off the weekend of March 19-21, 2021.   All guests will be welcomed with a locally handmade chocolate box in rooms.


    Wylder Hotel - Tilghman Island

    Chocolate Themed Specials in Tickler's Restaurant: Cocoa-Espresso Roasted Cowboy Steak for 2 with Bordelaise Jus, Cocoa-Sea Salt Dusted French Fries, Tarragon Aioli Cocoa-Mint Crusted Rack of Lamb with Roasted Fennel-Orange Gremolata Valrhona Chocolate Souffle with Chocolate Zinfandel Creme Anglaise

    Chocolate Indulgence package - $40


    • House made Chocolate Truffles

    • Tilghman Island Baking Company Chocolate Crabs

    • Mini bottle of champagne

    • Late checkout

    • Room upgrade

  • Upcoming Events

  • 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.

St. Michaels Maryland Business Association
 PO Box 1221, St. Michaels, MD 21663


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