Merchant Events

9th Annual Sykesville Shiver Shuffle 5K

Feb 28th, 1:00 PM. Come out and ‘Kill the Hill’ as you enjoy a mid-day 5k through Downtown Sykesville! Registered runners will receive a $5 coupon to use at any of the participating stores, pubs, or restaurants on Main St.

Check out our Mian Street deals by following this link or using this QR code:

  • Cash Awards to the Top 3 Overall (Male and Female)
  • Each finisher will receive ERR Race Gloves and a Finisher Medal
  • Raffle drawings will be randomly selected and you can claim your prize at the end of your run

As with all the ERR events we also have an outside charity benefit from this race. This year a portion of proceeds will go to the Maryland Food Bank. Maryland Food Bank has been hit hard this year because of the Coronavirus.

Register online at  


Get Lucky on Main

March 20th – Pick up your  Bingo card with purchase at any of the participating Main St. Stores. With any purchase at a participating store, you will get your card stamped. Five (5) in a row gets you Bingo and a chance to win a pot of gold. There will be several winners who will win a Pot of Gold consisting of gift cards from our Main Street Stores.


Storybook Character

May 21st  – Time TBA. Come dressed in your favorite storybook character and peruse Main Street. There will be trivia questions, raffle prizes and more. Mark your calendar!


Pride Day

June 13th – details to come soon. Specials in the making!


 Ladies night

Date TBD. Fun under construction!


Small Business Saturday

November 27th. Fun under construction!


12 hours of Christmas*

* or equivalent Holiday blast under construction!


*Photographs or videos of the event’s participants might be used for promotional or educational purposes.

Details will be made available on the DSC’s and participating merchants’ Facebook pages!



Upcoming Events

10:00 am 2021 Let Freedom Ring Parade @ Sykesville Main Street
2021 Let Freedom Ring Parade @ Sykesville Main Street
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2021 Let Freedom Ring Parade @ Sykesville Main Street | Sykesville | Maryland | United States
The Downtown Sykesville Connection is hosting its third “Let Freedom Ring Parade” on Saturday, July 3, 2021. The Let Freedom Ring parade will start at 10 am that day, beginning at Sykesville Middle School and … Continue reading 2021 Let Freedom Ring Parade
9:00 am The Coolest Golf Tournament @ Links at Challendon
The Coolest Golf Tournament @ Links at Challendon
Aug 20 @ 9:00 am – 3:30 pm
The Coolest Golf Tournament @ Links at Challendon
The Downtown Sykesville Connection (DSC) strives to diversify its programs and engage new volunteers. With the same Wonderwomen volunteers – Leslie George-Rowe and Denise Rowe – still actively working with the DSC team on the … Continue reading The Coolest Golf Tournament
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