St. Patrick's day festival & home brew competition | March 16, 2019

Visit us on March 16th for the annual beer festival and home brew competition. The event runs from 11am-4pm and features live music, corn hole tournament, crafts, great food, beer sampling, costume contest, and home brew competition. 

COWBOY UP! FESTIVAL | August 3, 2019

The Cowboy Up! Festival is sponsored by The Sikeston Depot Museum and features children’s activities, wagon rides, mechanical bull rides, a petting zoo, Lazy L Safari, Music in the Park, and many options for food, craft, and art vendors to enjoy as the Annual Sikeston Jaycee Bootheel Rodeo Parade ends in Historic Downtown Sikeston each year. 

wine festival | september 2019

The Annual Historic Downtown Sikeston Wine Festival has quickly grown into one of Sikeston’s largest events. Featuring samples from area wineries and hors d’oeuvres from Downtown businesses and sponsors, it is the perfect event for a night Downtown with friends or significant others. Listen to great music and enjoy fantastic local wines while Center Street is transformed into a beautiful scene perfect for a night out on the town. This event is for ages 21+ only. IDs are checked at the entrance. 

downtown garage sale | October 2019

The Downtown Garage Sale is a biannual event in conjunction with the Downtown Farmers’ Market. Profit from your Spring and Fall cleaning by setting up Downtown and selling or trading your items in a high traffic area. The vendor information form is below. Feel free to use PayPal to pay online, but please return or e-mail the form in addition to the online payment. 

holiday open house | November 2019

The Holiday Open House is Downtown’s version of an early ‘Black Friday’. Start your Christmas shopping early with special deals in all Downtown shops as well as visits with Santa, carriage rides, and holiday music. 

downtown Christmas tree lighting | December 2019

The Downtown Christmas Tree Lighting is an annual event with a very large tree lighting that is fun for the whole family. Events include Santa’s Mailbox, candy cane hunts, carriage rides, carolers, and pictures with Santa Claus. Downtown shops will also hold special sales this evening. Bring the whole family and celebrate Christmas in Historic Downtown Sikeston. 


Shop Downtown Sikeston during regular business hours and receive a chocolate treat from each participating vendor. You can also enter a drawing to win a Valentine Gift Basket valued over $500. More visits to businesses means more entries to win! Participating businesses are marked with red and pink balloons. 

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