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.

Latest Past Events

Christmas in the Valley

Downtown Middletown, Maryland 31 West Main Street, Middletown

Join us Saturday, December 4, 2021 and step back in time to this nostalgic-rich holiday event, complete with caroling, holiday music, our town tree lighting and of course a visit from Santa Claus! 4:00pm - 5:30pm & 6:30pm - 8:30pm Visit with Santa outside Town...


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...