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            • Fall into St. Michaels October 21-22, 2023

            • Fall into St. Michaels events 2023

            • The change of the season brings excitement and vibrant color to the Town of St. Michaels, as residents and businesses celebrate their annual harvest festival, Fall into St. Michaels, October 21-22, 2023.  Enjoy our fabulous restaurants, charming boutiques and galleries, or take a boat ride out on the water for some local history and sights.    Stay in our inns and B & B's for some much needed relaxation. The autumn months are a perfect time to visit St. Michaels for a romantic retreat or a family get away. 

              Fall into St. Michaels weekend starts with our annual scarecrow and pumpkin carving contest with businesses around town participating.   The annual pumpkin pie contest is back this year to benefit the St. Michaels Community Center, and will be held Saturday, October 21st from 10am - 2pm at the Union United Methodist Church, located next to the community center.   Businesses and residents wishing to take part in the pumpkin pie contest should bring 3 pies to be judged and sold to benefit the SMCC on Saturday morning.      There will also be pumpkin painting for children interested in participating.    St. Luke's Church Jewelry Sale will be held in Fellowship Hall from 10am - 2pm on Saturday as well.

              New this year, the inaugural Wag-O-Ween, will be held at The Preppy Redneck's back parking lot on Saturday, October 21 starting at noon.  There will be a dog costume contest, photos and a doggie trick-or treat at participating businesses, pick up your information at Wag-O-Ween Headquarters.   A kick off party will be held at Foxy's Harbor Grill on Friday night from 4pm-6pm and again on Saturday from 12pm-3pm.

              The Jack Russell races will return for a fun filled day for dogs and their owners.   It will be held Sunday, October 22nd at the St. Michaels Inn located at 1228 St. Michaels Rd, on the front lawn.   The races will be broken down into categories: Jack Russell, Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race. All dogs are welcome at the event, big or small, racing or not, to mingle with other dog lovers in Talbot County. Dogs under 25 pounds are welcome to race.  To register click here.

              This year's event will feature a small vendor village including Coffee & Doughnuts and a Bloody Mary & Mimosa Bar. There will be a 50/50 raffle from local businesses, including gift cards to area restaurants, to benefit our local partners.  All proceeds from the benefit will go to local dog charities.

              See photos of the 2022 Pumpkin Carving Contest here.


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            • The 2023 pumpkin pie baking contest will be held at the Union Methodist Church for the Fall into St. Michaels on October 21, 2023.

              To enter please bring three pies starting at 9am but no later than 10am to be submitted for the contest.  All proceeds will benefit the St. Michaels Community Center.

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            • Jack Russell Races - Sunday, October 22nd

              • Dog owners from all over Maryland join the residents of St. Michaels on Sunday on the lawn at the St. Michaels Inn for the annual Jack Russell Races. This year’s races will begin at 11:00 am.

                Register on Jack Russell Races Facebook page here.

                The races will be broken down into categories: Jack Russell, Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race. All dogs are welcome at the event, big or small, racing or not, to mingle with other dog lovers in Talbot County. Dogs under 25 pounds are welcome to race.

                This year's event will feature a small vendor village including Coffee & Doughnuts and a Bloody Mary & Mimosa Bar. There will be a 50/50 raffle from local businesses, including gift cards to area restaurants, to benefit our local partners.  All proceeds from the benefit will go to local dog charities. 

              • Navigate to the SMJRR Facebook page for more information here.

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            • Cannonball Run meets Scavenger Hunt!
              A day of commitment free riding enjoying a few hours of beautiful Talbot County roadways. All in the name of good fun, fundraising for the Classic Motor Museum and the comradery of fellow auto enthusiasts.

              Meet at Chesapeake Seafood 1216 S. Talbot St., St. Michaels  at 10:00 AM sharp.
              Instructions will be delivered to drivers and their team upon arrival. Teams will then plan their route according to their interests and the journey they want to experience.
              All participants must return by 1:30 PM to the old Mill complex  located across from the Classic Motor Museum and between E. Marengo St. and  E. Chew Ave., St. Michaels.
               

              Your participation in this event will take you all around the county while you hunt and scavenge the roadways for answers.
              It's a fun challenge for you and your friends/family. Pack your car with sandwiches, drinks, and people with sharp eyes and a sense of adventure. You're set, as long as you have a full tank of gas!
              Proceeds from this fundraiser will directly benefit the Classic Motor Museum's Automotive Technician Apprenticeship Program.
              Fees are per automobile:
              Non-Members $150.00
              Members $125.00
              Students $50.00
               
              Register here.
               
               
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            • Upcoming Events

            • Find Accommodations Find Accommodations

              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.

            • Local Eats & Drinks Local Eats & Drinks

              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.

            • Shopping in Town Shopping in Town

              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.

            • On the Water On the Water

              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

             info@stmichaelsmd.org

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