3rd Annual

Main Street Middletown Coloring the Street

Saturday, April 25, 2020

Join us for a day of art in downtown!

We’ll kick-off the event with street yoga, and will, again, host the community chalk art contest. We had over 100 participants last year, and space is limited, so make sure you check back often, as the sign-up link will be published sometime in February.

Special thanks to the Frederick Arts Council for awarding Coloring the Street a generous grant to offset the costs of this event. Main Street Middletown is a non-profit organization with limited funds, and as such, we hope support like this will allow up to bring this event to the community for years to come!

If you would like to make a donation to support Coloring the Street, click here. Please note Coloring the Street with your donation.


Selected Featured Artists will showcase their talents on the streets of downtown Middletown with amazing 8’x8’ chalk art displays. Featured Artist spaces are limited. If you are an artist, and would like to apply, please click here. Artists should submit applications no later than March 15th. Again, spaces are limited so apply early!

We will once again host the Community Chalk Art Contest, open to all ages and abilities. Join us for a day of transformation as we turn downtown Middletown into a community art gallery.

Our theme for this year’s contest is Heroes – fiction or non-fiction. Artists can choose to participate in the theme for a chance to win prizes. Freestyle artwork is also welcome!

Spaces are limited. To reserve your square sign up here and mail or drop off $5 to Town Hall – 31 West Main Street, Middletown, MD 21769.


A selection committee will choose unique and eclectic hand-crafted and art vendors. If you are interested in a vendor space, please click here to download the Vendor Application.



Coloring the Street offers a fun and unique opportunity for business sponsorship. Local artists will incorporate sponsor’s business name and/or logo into the artwork, prominently displayed. Sign up to sponsor one of our talented Featured Artists and also support this community art event. If you are interested in sponsoring a space please click here. Sponsorships are limited so apply early!


Thank you to our 2019 Sponsors

Mountain Spirit YogaHello Gorgeous Salon logo 


Main Cup logo

Deb's Artisan Bakehouse logo






Allstate logo

Shockley Honda logo

Lakeside logo




Kelley Real Estate Professionals logo

Tapia's on Main logoMiddletown Valley Bank logo








Thank you to the MHS Horticulture for donating the flowers

Coloring the Street


April 25, 2020


10:00 am – 3:00 pm


Strollers and leashed dogs welcome


Elm Street Municipal Lot, 123 Elm Street, Middletown, Maryland 21769

East Green Parking Lot, 102 E Green Street, Middletown, Maryland 21769