Walking along Main Street in historic Middletown is like journeying back into the past. Everywhere you turn, you’ll find reminders of the town’s long and storied history dating back to 1767. Main Street itself tells much of the story of this Frederick County community’s growth and development over the years. 


An aerial view of Main Street Middletown


Today, US-40 Alternate shadows the path of General Edward Braddock and Colonel George Washington on their ill-fated expedition toward Fort Duquesne (modern-day Pittsburgh) during the French and Indian War in 1755.

A few decades later, the National Road cut through the growing village of Middletown, bringing importance to the town as a trading center in the agriculture-focused economy of the valley framed on the east and west by Catoctin and South Mountains. The village also became one of the “pike towns” on the macadamized road running from Baltimore to the west over the Appalachian Mountains. 


View of Main Street Middletown

Travelers came to Middletown on the National Road and enjoyed the hospitality offered in the town’s hotels and restaurants. 

Among the most important visitors that came to Middletown arrived during the American Civil War. Several armies marched through the charming village, most famously in 1862 when Confederate and US soldiers used the National Road in what became known as the Maryland Campaign. The armies clashed just west of Middletown at South Mountain on September 14, 1862 and three days later at Sharpsburg in the Battle of Antietam. 


Drawing of Civil War Soldiers in Middletown circa 1862


The fighting made Middletown crucially important as a hospital town for the US Army, and wounded US and Confederate soldiers were treated in the town’s churches and private homes. These essential tales from American history are told today - discover stories from the Battle of South Mountain at South Mountain State Battlefield Park and Gathland State Park near Middletown. Learn more about the treatment of the wounded back in Frederick at the National Museum of Civil War Medicine. 


Gathland State Park sign and War Correspondents Memorial ArchThe War Correspondents Memorial Arch at Gathland State Park 

Come to Main Street and learn more about the town’s role during the war and as a hospital town with Civil War Trails, other local history wayside exhibits, and the Heritage Walking Tours created by Main Street Middletown.

Experience the hospitality that Middletown shared with travelers on the National Road and with the wounded treated here during the Civil War in the town’s restaurants and businesses. Grab a bite to eat at the Main Cup. This former ice cream factory offers delicious American-fare served up in a building dating to the turn of the 20th century, with plenty of great outdoor seating perfect for the summer months. 


View of the outside of the Main Cup

Don’t forget to take a moment to admire the beauty of the architecture and how it interacts with the surrounding landscape. The towering Zion Lutheran Church dominates the skyline with its steeple and town clock - the 1860 building also served as a shelter for the wounded during the Civil War. 


Zion Lutheran Church in Middletown

Any visit to Middletown would not be complete without an experience out on the farmland surrounding the town and tasting the bounty of the region’s incredible farmland. Make a visit to South Mountain Creamery for locally-made ice cream and other treats.


Fresh ice cream on the farm at South Mountain Creamery

Journey north of town to make a stop at Orchid Cellar, Maryland’s first meadery. Here, local honey becomes delicious honey wine, often infused with a variety of spices to create a unique beverage.




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