One of the pleasures of staying at Belle Orchard is how much sits within an easy drive. Boonsboro, Maryland, is small and quiet, but the towns around it each have their own character. If you are planning day trips from Boonsboro, MD, here are three destinations worth building a weekend around, along with a few stops right in town.

Start in Boonsboro

Boonsboro was founded in 1792 and still has a walkable Main Street shaped by the old National Road. Local museums, including the Boonsborough Museum of History and the Boonsboro Trolley Museum, offer a simple introduction to the area’s past.

If you visit in November, you may find downtown busy with runners. The town is the starting point of the JFK 50 Mile, which is known as the country’s oldest ultramarathon. A morning in town makes a gentle start before you head out for the day.

Hagerstown: Art, Trains, and a Historic Park

Hagerstown is the county seat of Washington County and its largest city, a short drive from Boonsboro. Hagerstown City Park is the natural place to begin. The Washington County Museum of Fine Arts sits in the park beside the lake, and admission is free. The collection includes American, European, and world art, with works by Thomas Moran and Norman Rockwell.

The Hagerstown Roundhouse Museum, inside a former railroad roundhouse, explains why the city is nicknamed the Hub City. Downtown, the Maryland Theatre has been a landmark since 1915 and is home to the Maryland Symphony Orchestra, so it is worth checking the schedule before you go. The Hagerstown Cultural Trail also connects City Park with downtown on a short, walkable route.

Shepherdstown, West Virginia

Across the Potomac River, Shepherdstown is a very walkable town, and the entire town is listed on the National Register of Historic Places. German Street is the center of it all, lined with 18th and 19th century buildings that now hold shops, galleries, and restaurants.

Start at the Historic Shepherdstown Museum on East German Street, where you can pick up a self-guided walking tour of nearly 60 stops. Then browse O’Hurley’s General Store, stop at the Shepherdstown Sweet Shop for baked goods, or order coffee at German Street Coffee-Candlery. The C&O Canal towpath is close by for anyone who wants a walk near the river. In July, the Contemporary American Theater Festival brings new plays to town.

Harpers Ferry, West Virginia

Harpers Ferry National Historical Park sits where the Potomac and Shenandoah rivers meet. The park recommends parking at the Visitor Center on Shoreline Drive and taking the shuttle bus to Lower Town, since parking in town fills early, especially on weekends. The Appalachian Trail passes through Lower Town, and the Appalachian Trail Conservancy has its headquarters in the town.

If your group is also interested in Civil War history, a day here pairs well with a visit to South Mountain and Antietam.

Come Back to Belle Orchard

The best part of a day trip is the return. Back at Belle Orchard, guests can unwind on the patio, gather around the fire pit, and share what they found along the way. Because the property is a private stay rather than a hotel, the group can spend the evening together instead of scattering.

Our Experiences page lists curated additions, such as private dining and creative workshops, if you would like to make the evening feel a little more special.

Tips for Planning Your Day Trips

• Choose one destination per day so nothing feels rushed.
• Check opening hours before you go, since museum and park schedules can change by season.
• At Harpers Ferry, park at the Visitor Center and take the shuttle into Lower Town.
• Pair a quieter walking town like Shepherdstown with a more active day outdoors.

Boonsboro puts a surprising range of places within reach, and Belle Orchard gives you a comfortable place to come back to each evening. We would be glad to welcome you.