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Middletown, Maryland will steal your heart, just like it did a young George Washington when he laid eyes on the Valley, exclaiming it was most beautiful. Today, this historic town retains much of its natural beauty and charm. Located in Frederick County, an easy drive from Baltimore, Middletown is the perfect destination for visitors, whether they come for the Civil War and American history, or to spend the day shopping, dining, and exploring the downtown.
A stop at the Welcome Center, operated by the nonprofit Main Street Middletown, MD Inc. is highly recommended to get oriented to the area. Visiting Middletown in any season is noteworthy, but springtime in Middletown is especially pretty. Middletown was founded in 1767 and is located on the Old National Road—the nation’s first federally-funded highway. Often called America’s Main Street, the Old National Road carried settlers west, and each town was a vital stop for those early travelers. Driving through Middletown will take you by over 250-years of architectural history, though for a slower view, we recommend taking a heritage walking tour.
It was not just travelers who trod the Old National Road. Middletown is located west of Monocacy Battlefield, south of Gettysburg, east of Antietam, and adjacent to the Maryland Battle of South Mountain. During the Civil War, troops—both Union and Confederate—marched through town, and in the aftermath of the fighting, buildings were quickly converted to hospitals to care for the wounded.
There is a sweet side to history, too. Due to the rich dairy farms, Middletown has long been an epicenter of ice cream manufacture, and our Ice Cream Trail in summer is not to be missed. One of our stops on the Ice Cream Trail includes LDS, which holds the distinction of possessing the oldest license in the country to sell Hershey’s Ice Cream. It’s just one way contemporary Middletown respects its history while embracing the present. Nearby wineries include Willow Oaks Craft Cider and Wine, and Orchard Cellar Meadery and Winery, Maryland’s first Meadery.
In town, the 110-year-old Gladhill Furniture Company is a popular destination for aesthetes seeking furnishings that will age gracefully into family heirlooms. The Turquoise Trailer Boutique offers customized cowgirl hats, clothing, and accessories, Hello Gorgeous Boutique is a women’s clothing destination with clothes that will take you from work to dinner, and the Trolly Stop is the perfect location to find locally crafted and curated home products and art. Be sure to visit Middletown Sportsland, another Middletown landmark, having served Frederick County with sports clothes, uniforms, and gear for the last 40 years.
While the town may be home to just around 5,000 residents, Middletown punches well above its weight when it comes to its dining scene. From barbeque to Italian cuisine, there is no shortage of restaurants. Just a few highlights include Abbraccio Gelato, where the sweet treat is made fresh daily, Aleko’s Village Cafe, named Best Greek Restaurant in Frederick County for many years, Tapia’s on Main for superb paninis, Dempsey’s Grille, the local diner for comfort food, and The Main Cup, a Middletown original that has served the area fresh American fare so delicious that it draws patrons from afar. Others come to Middletown specifically to seek out Deb’s Artisan Bake-House, for savory and sweet delights. But come early, as there is often a line in the morning. Of course, a stop at Beans and Dreams will keep you well-caffeinated.
After all the good food, drinks, and ice cream, a stroll may be in order. Heritage Walking Tours can be arranged at the Welcome Center or accessed via cell phone. For those looking for more adventure, the Appalachian Trail head is just a few miles west of town.
Middletown is a timeless treasure near Baltimore and we welcome you to the Valley. Visit the Welcome Center to learn more about Middletown’s Civil War history, places to shop, stay, and dine, special events, and more. Learn more today.
