• St. Michaels ChocolateFest

  • 2020 ChocolateFest Event Sponsors:


  • The Second Annual St. Michaels ChocolateFest will be held the first weekend in March on Saturday, March 7th and Sunday, March 8th, 2020.    

    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, or partake in Simpatico's Italian Wine-Spirits-Liquers-Chocolate Cheese tastings held March 7th and 8th from 11 am - 5 pm.     Join in the fun during the inaugural Chocolate Pie eating contest, or start your day off with the Hot Chocolate Run/Walk then head into town for the ChocolateFest Crawl.   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 7th from 11:00 a.m. - 4:00 p.m. during the ChocolateFest Crawl, sampling amazing artisan chocolates, desserts, wine, beer and spirits.    Limited supply, don't delay!   The ChocolateFest Crawl is a rain or shine event.

    Purchase tickets for the ChocolateFest Crawl on Saturday, March 7th here.  

    St. Michaels ChocolateFest Events

    ChocolateFest Crawl - Saturday, March 7th, 2020  11:00 a.m. - 4:00 p.m.  Rain or Shine event

    2nd Annual St. Michaels ChocolateFest Crawl, Saturday March 7, 2020 

    Each ticket may be redeemed at participating Tasting Venues listed below during the Chocolate Crawl during the hours of 11 a.m. - 4 p.m. on Saturday only.
    Choose from thousands of amazing chocolate concoctions, desserts, candies and drinks at participating tasting venues throughout the Town of St. Michaels.

    Purchase tickets for the ChocolateFest Crawl here.

    More details to follow about other exciting events during the weekend of St. Michaels ChocolateFest.

    MAP for CHOCOLATE CRAWL can be viewed here.

    SPECIAL EVENTS for CHOCOLATEFEST Weekend can be viewed here.




    Saturday, March 7th, 2020  11:00 a.m. - 4:00 p.m

    Rain or Shine event

    2nd Annual St. Michaels ChocolateFest Crawl, Saturday March 7, 2020 

    Each ticket may be redeemed at participating Tasting Venues listed below during the Chocolate Crawl during the hours of 11 a.m. - 4 p.m. on Saturday only.
    Choose from thousands of amazing chocolate concoctions, desserts, candies and drinks at participating tasting venues throughout the Town of St. Michaels.

    Purchase tickets for the ChocolateFest Crawl HERE.

    IMPORTANT: Simpatico's ChocolateFest Italian Wine-Spirits-Liquers-Chocolate Cheese Tastings Venue will be both Saturday and Sunday, see information located above for more details and ticket information.

  • ChocolateFest Crawl tickets are LIMITED!   

    Please Pre-Purchase ChocolateFest Crawl Tasting Tickets thru Wednesday, March 4th (ONE TICKET per TASTING- Sold in packs of 10) HERE

    Pick up your pre-purchased tickets Saturday starting at 10:00 a.m. at the ChocolateFest tent! 

    Tickets will not be mailed.

    Tickets will be available for purchase on Saturday starting at 10:00 a.m. at the corner of Railroad Ave and Talbot St. at 100 S. Talbot Street

    Chocolate Crawl Tasting Venues

     Saturday, March 7th 11 am - 4 pm

    AH Home 210 S. Talbot Street

    American Holiday  213B S. Talbot Street

    Ava's Pizzeria & Wine Bar - 409 S. Talbot Street

    Bistro/Royal Oak Catering - 403 S. Talbot Street

    Come By Chance - 202 S. Talbot Street 

    DBS Fine Jewelers  - 308 S. Talbot Street

    Sprout - 114 S. Talbot Street

    Guilford & Company and Inn at Perry Cabin - 101 N. Talbot Street

    Hopkins Original Art - 310 S. Talbot Street

    Knotty Living - 208 S. Talbot Street

    Ophiuroidea - 100 S. Talbot Street

    Olivin's - 110 N. Talbot Street

    Silver Linings - 203 S. Talbot Street

    Simpatico - 104 Railroad Ave

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

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

    St. Michaels Winery - 609 S. Talbot Street

    The Blue Crab - 102 S. Fremont Street

    The Galley - 305 S. Talbot Street

    Theo's Steaks, Sides & Spirits - 409 S. Talbot Street

    The Preppy Redneck - 213A S. Talbot Street

    Tilton Hilton -  100 Carpenter Street

  • Events Around Town



    Italian Wine-Spirits-Liquers-Chocolate Cheese Tastings Venue

    Saturday, March 7 & Sunday, March 8  11am - 5pm

    104 Railroad Ave


    Purchase Wine-Liqueur-Spirits-Chocolate & Cheese Tasting Tickets Here

    Be prepared for two days of chocolate delight from 11 AM to 5 PM on Saturday, March 7th and Sunday, March 8th!  

    Join us in our heated tent and in the shop for special paired tastings of fabulous wine, chocolate, liqueurs, spirits, cheese & more!  Enjoy 5 ($8) or 10 ($15) Tastings of hand-selected wines, liqueurs and spirits paired with fabulous chocolates and Italian cheeses.  You will be presented with 5 or 10 tickets or more, based on your total ticket purchase, when you check in for registration at Simpatico. The tickets can be used to redeem for the equal number of Wine-Liqueur-Spirit-Chocolate-Cheese tastings offered at our venue.

    PLEASE NOTE: Saturday only -  Chocolate Crawl tickets can be redeemed for chocolate tastings only in the Simpatico tent.

    Simpatico is offering a lineup of their favorite Italian red, white and sparkling wines and Dark and White Chocolate liqueurs and Spirits to taste with Italian chocolates and cheeses, all especially paired for your delight. You can learn about how to pair the various types of chocolates with wines, cheeses, and spirits. They will also have regional artisan Chocolate makers with their delightful chocolates to taste and purchase under their heated tent.    And finally, they are offering tastings of their Italian Chocolate Desserts, Biscotti, Cookies, and more!  Don’t miss out on the fabulous offerings at Simpatico's venue during St. Michaels ChocolateFest.

    Pairing event tickets are LIMITED, purchase Wine-Liqueur-Spirits-Chocolate & Cheese Tasting Tickets HERE. 

    Chocolate-Wine-Liqueurs-Spirits-Cheese we will be tasting in Simpatico's heated tent and in the shop on Saturday and Sunday.
    Attendees can choose which tastings to try out of the selections offered. Saluti!



    Sunday, March 8th Noon - 4pm

    Taste & Vote for the “Best Chocolate Dessert”


    Taste 5 of 10 Chocolate Desserts for $5 and vote for the “People’s Choice Award” on Sunday, March 8th while visiting the Simpatico venue for St. Michaels Chocolatefest. Charity donation to be paid out of proceeds.

    Then enjoy tastings of Italian wine, liqueur & spirits paired with fabulous Italian chocolates & cheeses (tickets sold separately)


    TriCycle and Run

    929 S. Talbot Street   

    Saturday, March 7th 8am - 10:30am

    Kick off your morning with a beautiful 5k (3.1 mile) run/walk and burn off those calories (so you can fill them back up with delicious CHOCOLATE!!!!) before heading in to town for all the festivities.

    The course will take you on the St. Michaels Nature Trail, with a few minor road crossings. Participants will check in at TriCycle and Run, located at 929 S. Talbot Street, before heading over to the start area.


    Packet pickup and registration begin at 8am, with the run/walk starting promptly at 9am.  

    Participants should park at the St Michaels Elementary School parking lot (100 Seymour Avenue, St Michaels, MD). 

    Awards will be given out for Overall Winners, as well as age groups. 



    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 7, 2020. Facebook event here.





    The Galley 

    Saturday starting at 4 p.m.

    Arrive by 3:45 p.m.

    Chocolate Pie Eating Contest for all ages!

    Do you have what it takes to win?
    Kids and Adult Categories... delicious pie AND fun prizes! Participants will need to register below to enter the contest!

    Enter contest here.

    Facebook event here.



    St. Michaels Community Center

    103 Railroad Ave.

    Saturday, March 7th 10 am - 3 pm

    Local crafters and bakers will be offering ChocolateFest themed items for sale at the community center.

    Facebook event here.

  • More Specials during ChocolateFest weekend March 7 - 8, 2020

    Awful Arthur's Seafood Company  402 S. Talbot Street

    Special pricing on Chocolate items: 

    Chocolate covered pretzel martini  $8     Chocolate peanut butter cup martini $10     

    Chocolate Smith Island cake $6      Chocolate mousse $6


    Carpenter Street Saloon  113 S.  Talbot Street

    ChocolateFest Special items coming Soon





    Inn at Perry Cabin    308 Watkins Lane

    $6 Choco-tini (Chocolate Martinis) at Purser’s Pub- only on March 7th

    Spa Treatment- Chocolate Fest Massage-50 minute Custom Massage that includes a Rose and Chocolate foot scrub and wrap $145.

    We will also hand out a coupon for a Tues-Friday offer for the month of March- Book a 50-minute massage or facial and get 30 minutes free for a total 80-minute treatment.



    The Old Brick Inn   401 S. Talbot Street

    We have put together an all-inclusive chocolate, wine, & cheese package for ChocolateFest Weekend in St. Michaels! This deal will include an exclusive 30 Ticket deal to Simpatico’s ChocolateFest that can only be found HERE!
    PLUS~Guests will receive Chocolate, Wine, & Cheese during their stay at OBI. We promise you won’t want to miss out on this Sweet Deal and rooms are filling up FAST!! Call us today at 410-745-3323 to claim your event package, Friends!!


    Olde Town Candy Co.     216 S. Talbot Street

    15% off bulk chocolate, loose and pre-packaged.

    10% off Handmade candies and truffles.  



    St. Michaels Inn   1228 S. Talbot Street

    Come to town for ChocolateFest and stay the night with us at St Michaels Inn. The ChocolateFest Package includes a One Night Stay and a bottle of wine and chocolate of course. Our lobby will feature chocolate treats throughout the weekend, breakfast may even include a little chocolate! Call the Inn at 410-745-3333 to book your weekend. 


  • 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.

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


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