Things to Do in Boonsboro, MD

If you’ve been craving a peaceful mountain town with a little Civil War history and a touch of literary magic, I can’t recommend Boonsboro enough. I’ve wandered its scenic streets, hiked the nearby trails, and fallen for its small-town charm again and again. Nestled at the base of South Mountain, Boonsboro feels like a step back in time—but one you’ll want to linger in. You’ll find historic overlooks, cozy inns, and places that make you feel like you’re part of a story. Whether you're tackling the Appalachian Trail, staying in a romance-themed inn (yes, I’ve done it!), or retracing history on old battlefields, Boonsboro is full of surprises.

Boonsboro, MD Highlights I Think You’ll Love:

• For Adventurous Travelers: Hike to Washington Monument State Park – I’ve climbed this one myself, and the views from the first monument dedicated to George Washington are absolutely worth the effort.
• For History Buffs: Explore South Mountain State Battlefield – If you love Civil War history like I do, you’ll want to walk this site and imagine what happened here during the Maryland Campaign.
• For Shoppers: Browse Turn the Page Bookstore – I always make a stop here. It’s owned by Nora Roberts’s family and has such a warm, bookish energy. You might even meet a fellow fan.
• For Couples: Stay at Inn BoonsBoro – I stayed here on a weekend getaway and felt like I was living in a novel. Each room is inspired by a literary couple—it’s romantic without being over-the-top.
• For Families: Picnic at Shafer Park – If you’re traveling with kids, you’ll appreciate the laid-back vibe, playgrounds, and room to stretch out. I’ve seen plenty of locals enjoying summer evenings here.

When I’d Recommend Visiting Boonsboro, MD

I’ve found the sweet spot for visiting Boonsboro is April through October. If you love hiking, spring and fall offer the best weather—and the colors on South Mountain are breathtaking. Summer’s great too, with festivals and outdoor fun, but I’ve also enjoyed a winter visit when the town is quieter. That’s when you’ll want to cozy up with a good book and a glass of wine at the inn.

How I’d Get to Boonsboro, MD

• If you’re driving: I usually take MD-34 or MD-66—Boonsboro’s about 1.5 hours from both D.C. and Baltimore, and the scenic drive makes it feel like an escape.
• By Air: Hagerstown Regional (HGR) is just a short drive away. I’ve also flown into Dulles or BWI when planning a longer stay in the area.
• By Train: You can hop on Amtrak or MARC to Harpers Ferry or Frederick. From there, I’d recommend a car rental or rideshare—Boonsboro is best explored at your own pace.

Where I’ve Stayed (and Where You Might Like to Stay) in Boonsboro, MD

• For Couples: Inn BoonsBoro – I fell in love with this place the first time I walked in. It’s elegant, personal, and the literary touches make it unforgettable.
• For Families: Quality Inn & Suites Hagerstown – It’s just a short drive away and great if you need space, a pool, and a reliable breakfast before a day of exploring.
• On a Budget: Antietam Overlook Farm B&B – I’ve stayed here for the views alone. Rustic, peaceful, and close to everything—this spot feels like a hidden gem.

Best Things to Do in Boonsboro, MD