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

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

Join us for a day of art in downtown Middletown, Maryland where the streets will be full of relaxing music, delicious food, eclectic vendors, great wine and amazing art produced by both local professionals and art enthusiasts alike! This incredible event kicks off with free street yoga and continues with the wildly popular community chalk art contest welcoming all ages and abilities!  Parran Collery, professional ceramic artist, will offer children the opportunity to paint ceramic tiles which she will later…

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May 2020

Heritage Walking Tour

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

RAIN DATE  Sunday, May 17, 2020 1:00 p.m. to 5:00 p.m. Price $10 per person, children under 16 are free. Tickets may be purchased online in advance or at Christ Reformed UCC the day of the event. Tour begins at the historic Christ Reformed UCC, 12 South Church Street, Middletown, Maryland 21769.    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…

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June 2020

Vintage Vehicles in the Valley

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

Fun for the whole family! One of a kind cars, trucks and motorcycles! Delicious food, games, raffles and live classic rock and roll by Simple Pleasure! To benefit the Warrior Canine Connection. Registration 8:30 a.m. - 11:00 a.m. Registration Fee $15 per vehicle, $10 for each additional vehicle by the same owner. Dash plaques for the first 100 registered vehicles.  Show Open Free to the Public 11:30 a.m. - 2:30 p.m. People's Choice Trophy to be voted on by you! …

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