Maryland's Fairytale Town With Mountain Views And A Charming Downtown Is A Quaint Getaway

Just 20 minutes away from one of the most important towns in American history, Harpers Ferry, lies one of Maryland's best historic and charm-filled getaways. Boonsboro, tucked along the western border of Maryland at the base of South Mountain, was first founded in 1792 and incorporated a few decades later in 1831. 

Whether you're looking for another city to pair with your time in the oldest town in West Virginia, Shepherdstown (which is less than 20 minutes away), or a base for embarking on sections of the Appalachian Trail, this rural community has lots to offer visitors, whether they're seeking gorgeous mountain scenery or an idyllic downtown. 

For a cozy, history-rich stay, try the eight-room Inn BoonsBoro, a bed and breakfast located right downtown. It's located on a property dating back to the 1790s, and offers features like a two-course breakfast, complimentary wine and charcuterie each evening, and free parking. The inn has a 4.8-star rating on Tripadvisor. Hagerstown Regional Airport is the closest airport to Boonsboro, just 30 minutes from town and offering limited seasonal flights through Allegiant Air. For more flight options, Washington Dulles International Airport is about an hour away.

With historic buildings lining its downtown — especially along Main Street — Boomsboro is full of fairytale charm. For some quaint, small-town shopping, head to Cronise Market Place, which has been a hub for fresh produce, and locally-made decor, desserts, and more, since 1928. Gifts Inn BoonsBoro is also a local staple for art, decor, handcrafted body care items, jewelry, and other goods, all created by regional artists. 

Don't overlook some of Boonsboro's historic sightseeing, either. Since its founding, Boonsboro has witnessed fascinating history. The 1862 Battle of South Mountain was the first battle of the Civil War to reach the North. Be sure to explore some of Boonsboro's storied past and beyond at the Boonsborough Museum of History, open every other weekend from May through December, or by appointment. This small museum packs an extensive collection, consisting of a little bit of everything, including artifacts from Ancient Egypt and the Civil War. Entry is $5. The Boonsboro Trolley Museum is another historic gem, dating back to the early 20th century. The museum is inside the town's trolley station, which houses a collection of photography and artifacts. It's currently open by appointment only. 

When you've worked up an appetite, you'll also find a number of beloved eateries in town, such as Jeovani's Pizzeria, which has a 4.5 rating on Google, and Sizzling Fajita, which offers an array of tacos, burritos, and other Mexican dishes.

Framed by the Blue Ridge mountains, Boonsboro is steeped in natural beauty. Don't skip some time at Washington Monument State Park, where you'll find an original presidential monument and a scenic trail. The 34-foot-tall monument — a stone tower built back in 1827 in honor of George Washington — is known as a great birdwatching spot. And if you're looking to explore a bit of the scenic Appalachian Trail, which runs from Georgia to Maine and has about 40 miles winding through Maryland, you'll also find that here. Or you can head to Greenbrier State Park, South Mountain State Park, or Gathland State Park to explore a different area.

Boonsboro's best nature isn't all above ground, either. Crystal Grottoes Caverns is another must-see, with stunning caverns and mystical beauty. Accidentally discovered by construction workers back in 1920, the caves have been open to the public since 1922 and have remained relatively unaltered since. Here, you can wander through nearly 900 feet of limestone caves that date back 500 million years — a truly unforgettable journey through the past. Adult admission (ages 13 and up) is $23.