Middletown Maryland - A Great Place To Live


The early German and English settlers started to arrive in the valley in the 1730s. Among them was Michael Jesserong, who bought for 50 acres. He named his property Middletown and sold the first lots there in 1767, the date officially marked as that of the town's founding.The history of Middletown is a mirror on the nation's development. Main Street spread to the west with construction of the National Pike through the town in 1806; the telegraph lines from Frederick to Hagerstown were routed through Middletown in 1854; and in 1896, car 11 of the Frederick Middletown Railway made its first run to Middletown. During the Civil War, both armies passed through the town to the battles of South Mountain and Antietam. In the aftermath of those battles, Middletown opened its churches and homes to care for the wounded.

Main Street Middletown is where breathtaking views and historic landmarks greet you as you make your way down the mountain to fresh American fare, just churned ice cream, one of a kind shops, wineries and one of Maryland’s only meaderies. Beyond offering live entertainment, fine art, shopping and dining Main Street Middletown offers events for your family’s next adventure and is located just miles from the Appalachian Trail head. Whether you are seeking a relaxing day surrounded by spectacular scenery, a walk in the footsteps of George Washington, or for a farm-fresh dining experience, Main Street Middletown welcomes you to the valley.

It is bound to the west by South Mountain, to the east by Catoctin Mountain, to the south by the Potomac River and to the north by the convergence of South Mountain and Catoctin Mountain, south of Quirauk Mountain. Geographically, it can be considered an extension of the Loudoun Valley which lies below the Potomac in Virginia. The valley derives its name from Middletown, the largest town in the Valley. The use of the Catoctin Valley terminology was prevalent up through the American Civil War but afterwards was abandoned due to confusion between it and the northern portion of the Loudoun Valley also referred to as Catoctin Valley. 


For a small town, Middletown offers more than graceful historic buildings! They offer a variety of delicious restaurants to tempt and treat, from comfort food to farm-to-table freshness, but be sure to save room for dessert! Their friendly services offer incredible and convenient options for residents, employees and visitors alike – state of the art salons, beautiful spas, fitness studios and more – all within our walkable downtown. Many of the businesses have dedicated generations to their professions. The retail stores offer tailored shopping experiences and each customer is treated like family.

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