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When a young George Washington encountered Middletown, he exclaimed it was the most beautiful valley he’d seen. Today, this historic town retains much of the natural beauty and smalltown charm that captured the eye of that Founding Father all those years ago. 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, the arts, access to the Appalachian trail, or the excellent dining and shopping.
A stop at the Welcome Center, operated by the nonprofit Main Street Middletown, MD, Inc., is an excellent way to get oriented to the area. And there’s no better time to visit than now as the United States celebrates in 250th birthday. Middletown was founded in 1767 and is right on the Old National Road—the nation’s first federally-funded highway. Often called American’s Main Street, the Old National Road was a vital stop for early travelers. Driving through Middletown is like passing by 250 years of architectural history, though for a slower view take 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 local hospitals and buildings took in wounded after the battles of South Mountain and Antietam.
There’s a sweet side to history, too. Due to its rich dairy farms, Middletown has long been an epicenter of ice cream manufacture and the Ice Cream Trail in summer is not to be missed. It’s just one way contemporary Middletown respects its history while embracing the present. Other opportunities to explore today’s Middletown include visiting its nearby wineries and one of Maryland’s only Meaderies located at Orchid Cellars Winery.
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, and The Trolley Stop is the perfect location to find locally crafted and curated home products and art.
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. Just a few highlights include Abbraccio Gelato, where the sweet treat is made fresh daily, and Aleko’s Village Café, named Best Greek Restaurant in Frederick County for many years. Beans & Dreams Coffee House and The Main Cup keep visitors and locals well-caffeinated while Deb’s Artisan Bake House provides the European-style pastries—but come early as there’s often a line in the morning.
From barbeque to Italian cuisine, there’s no shortage of restaurants. But for a truly one-of-a-kind experience, visit LD’s Café. Yes, it is in a gas station, but its no-frills, quintessential diner vibe is part of its charm. Fun fact: it holds the oldest license in the country to sell Hershey’s Ice Cream.
Those in need of a strenuous walk after a good meal don’t need to go far; access to the Appalachian Trail is right near town.
Middletown is a timeless treasure near Baltimore and ready for exploration. Visit the Welcome Center to learn more about Middletown’s Civil War history, places to shop, stay, and dine, year-round events, and more. Learn more today.
