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In particular, Middletown played several fascinating roles in the Civil War. The whole town was held for ransom just a few days before the nearby Battle of Monocacy, with Confederate Lt. Gen. Jubal A. Early demanding $5,000 lest he and his troops burn the town to the ground. (The town managed to escape destruction with a negotiated payment of $1,500.) After the battles of South Mountain and Antietam, local homes and makeshift hospitals were used to care for both Union and Confederate soldiers, as well as future President Rutherford B. Hayes.

Guests can learn more about Middletown’s Civil War history and other important eras by visiting the Middletown Valley Historical Society on Main Street, where events, lectures and tours are hosted year-round. Visitors can honor local veterans who served in World War II, Korea, Vietnam, the Gulf War and the War on Terror at the Middletown War Memorial.

4. Journey through 250 years of architectural design. You Don’t Stop Making Instruments When You Get Old Poster

As Middletown has stood since 1767, more than two-and-a-half centuries of evolving architectural design are evident as you walk, bike or drive through town.

In particular, the town’s three-mile stretch of the National Road acts as an essential time line of Middletown’s development, with Victorian homes toward the east end of the road to German-influenced design, Gothic Revival, Greek Revival, Federal style, log cabins and Queen Anne homes along the route. Travelers venturing farther down Jefferson Street will see the site of Middletown’s historic free Black community, where non-enslaved African Americans abided prior to the end of the Civil War.

To help guests critically analyze the town’s different periods of development, Middletown offers six walking tours, each focused on a different era of Middletown history. Printed brochures are available at Town Hall, the Main Street Middletown office or the Frederick Visitor Center. An interactive map is also available at bit.Ly/3txA3tJ.

5. Take in the great outdoors.

Walking tours aren’t the only way to make the most of the fresh mountain air in and around Middletown. Parks, outdoor entertainment and other open-air offerings abound throughout the town.

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