Downtown Sykesville Shops


Welcome to Downtown Sykesville

Sykesville is a quaint small town, home to 4,400 residents. This unique and charming Town strives to maintain its historical heritage while fostering a vibrant and exciting downtown, rich in extraordinary art displays, eclectic activities, and exciting events programmed by the Downtown Sykesville Connection. The mission of the Downtown Sykesville Connection is to coordinate initiatives that enrich the quality of life of the downtown Sykesville community through the implementation of the Main Street Approach. The Downtown Sykesville Connection acts as the economic department of the Town of Sykesville. The Downtown Sykesville Connection received the Coolest Small Town in America by Budget Travel in 2016 and was crowned Best Main Street in America by Independent we stand June 2nd of 2020.

What’s new and exciting?

Whether you are a golf enthusiast or a Coolest Small Town & Best Main Street in America fan, we have great news!
Our organization added a fundraiser to its calendar of events and this one is already compliant with the current stage of the Maryland Road to Recovery plan. Our brand new Coolest Golf Tournament was designed to support our organization and fundraise for the fight against aplastic anemia, a condition that took Donna Carroll Box too early. The event will be a celebration of Donna’s life and togetherness, in the format that currently allows social interaction.
The Coolest Golf Tournament is scheduled for August 7th, details can be found on our Facebook page and website:
Check the event description for details!
A huge thank you to our sponsors for making this event possible!
Coolest Sponsors
                   Mueller Homes                                                 Murrow & McCullough
                                                                                                   Corner House Reality


If you need to stretch your legs while practicing social distancing downtown Sykesville, enjoy the tiny murals and their story: click the icon below to find the paintings and listen to his story

Upcoming Events

9:00 am The Coolest Golf Tournament @ Links at Challendon
The Coolest Golf Tournament @ Links at Challendon
Aug 7 @ 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 Leslie George-Rowe and Denise Rowe recently joining the DSC team and sharing Denise’s sister’s story, it just made sense to … Continue reading The Coolest Golf Tournament
12:00 pm 10th Annual Art & Wine Festival @ Sykesville main street
10th Annual Art & Wine Festival @ Sykesville main street
Sep 12 @ 12:00 pm – 5:00 pm
10th Annual Art & Wine Festival @ Sykesville main street
We came together by staying apart. Sykesville Art & Wine Festival, on Saturday September 12, 12 to 5pm The Downtown Sykesville Connection (DSC) decided to add to the 8 weeks confinement period implemented by the … Continue reading 10th Annual Art & Wine Festival
Hammond Law, LLC

This Week on Main Street

Appearances in the news, upcoming initiatives, how the community connects on Main Street, and so much more is happening. Find out what's up right here.
Read more