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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October 2019

Growing Up in Middletown

October 16

Presented by John Gladhill. Sponsored by the Middletown Valley Historical Society

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Middletown Farmers Market – Closing Day Scarecrow Festival

October 17 @ 4:00 pm - 7:00 pm
Middletown Farmers Market, 12 S Church Street
Middletown, MD 21769

Enjoy the Closing Day Scarecrow Festival and acoustic music from 5-6pm. Browse our vendors selling arts & crafts, baked goods, dairy meats & eggs, live plants & cut flowers, pet care products, hot/prepared foods, adult beverages & kombucha, local honey, fruits & vegetables, and providing services.

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Scarecrow March on Green Street!

October 19 @ 2:00 pm - 5:00 pm
Green Street

Visit Green Street on Saturday, October 19 for our annual Scarecrow March. Cast your vote for your favorite scarecrow! Snacks and beverages available.

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Halloween Parade

October 26
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November 2019

Trolley with Reuben Moss

November 20

Sponsored by the Middletown Valley Historical Society

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