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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.

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Vintage Vehicles in the Valley

19 W. Main Street, Middletown, MD 21769 19 W. Main Street, Middletown

DELIGHTFUL FAMILY FUN SATURDAY, SEPTEMBER 11, 2021 Take a walk down memory lane as countless rarely seen cars, trucks and motorcycles are on display to the public for one day only in downtown Middletown! Relax and take in the music performed live by Simple Pleasure,...

Free
Scarecrow March

Scarecrow March

19 W. Main Street, Middletown, MD 21769 19 W. Main Street, Middletown

VOTE FOR YOUR FAVORITE BETWEEN 2:00 P.M. – 5:00 P.M. Strollers and leashed dogs welcome Come see the cutest, craftiest, craziest collection of scarecrows in Maryland for the 13th annual Scarecrow March in downtown Middletown. Local residents and businesses vie for the scarecrow kits (we...