Our valley elevates community fun throughout the year. Main Street Middletown hosts fundraising opportunities annually in order to continue supporting our area businesses and events.

We celebrate our community, history, and culture. From the annual Heritage Festival to October’s spook-tacular Halloween Parade, we salute small-town life loud and proud.


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April 2020

Coloring the Street Chalk Art

April 25 @ 10:00 am - 3:00 pm
Green Street

Coloring the Street is the opportunity for friends and families to visit downtown Main Street!  Start the morning off just right with the unique experience of yoga on Main Street!  Event will feature chalk artists, opportunities to try your hand at your own chalk art drawing, music, food, wine, and much more!    

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May 2020

Heritage Tour of Middletown 2020

May 16 @ 10:00 am - 2:00 pm

Join us for the 2020 Heritage Tour of Middletown Old East Main Street Historic District Price: $10 per person SATURDAY, MAY 16, 10:00 am to 2:00pm RAIN DATE - SUNDAY, May 17, 1:00 pm to 5:00 pm Until the early 20th century, the area between Church and Broad streets was mostly farmed or undeveloped. Present-day Broad Street was the town’s eastern boundary. As Middletown grew, Church Street became the dividing line between West and East Main Street. Despite the development…

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June 2020

Vintage Vehicles in the Valley *Third Annual* 2020

June 13 @ 11:30 am - 2:30 pm
Green Street

Registration: 8:30am - 11:00am Show Open Free to the Public: 11:30am - 2:30pm W. Green Street, Middletown, Maryland 21769  Parking:  Elm Street Municipal Lot, 123 Elm Street, Middletown, Maryland 21769 East Green Parking Lot, 102 E Green Street, Middletown, Maryland 21769

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