10 Easy Road Trips From Charles Town, WV: Fun Things To Do Nearby
Looking for
fun things to do near Charles Town, West Virginia without driving all day? You’re in a great spot. Charles Town sits close to the borders of Virginia, Maryland, and the rest of the Eastern Panhandle, which means you’ve got a lot of options for short, out-of-county adventures.
Every trip on this list starts in
Charles Town (Jefferson County, WV) and heads into one of these nearby counties only:
Washington County, MD • Clarke County, VA • Frederick County, VA • Loudoun County, VA • Berkeley County, WV
Most of these spots are about 20–60 minutes away, making them perfect for a half-day escape or a relaxed weekend outing.
1. Washington County, MD – Explore Historic Hagerstown & City Park
If you want a mix of history and slow-paced charm, drive up to
Hagerstown in Washington County, Maryland. It’s usually around a 45–50 minute drive from Charles Town, depending on traffic.
At the heart of town, you’ll find
Hagerstown City Park, which feels like a little oasis in the middle of the city. There’s a lake with ducks and geese, shady walking paths, and even small museums tucked inside the park.
- Walk the lakeside paths and watch the ducks paddle by.
- Step into the Washington County Museum of Fine Arts right in the park.
- Bring a picnic and relax under the big old trees.
I remember one summer afternoon wandering around City Park and thinking it felt more like a quiet college campus than a city park. The pace is slow, the people are friendly, and you don’t feel rushed.
If you’re craving a low-stress day with a bit of culture, this is an easy win.
2. Antietam National Battlefield – A Powerful Day Trip in Washington County, MD
Just northeast of Charles Town, about a 30–35 minute drive, you’ll find
Antietam National Battlefield near Sharpsburg in Washington County, Maryland. This is one of those places where you can literally feel the history under your feet.
This is the site of the
bloodiest single-day battle of the Civil War. But today, it’s peaceful, quiet, and deeply moving.
- Stop at the visitor center for an overview and short film.
- Drive the self-guided tour route with stops at key points like the Cornfield and Burnside Bridge.
- Walk a short trail and just soak in the landscape.
If you like pairing
history and scenic views, Antietam is hard to beat. It’s a great place to bring kids or visitors who want to understand more about the region’s past.
3. Harpers Ferry from the Maryland Side – Canal Towpath & River Views (Washington County, MD)
You might already know Harpers Ferry from the West Virginia side, but seeing it from
across the river in Maryland feels like a whole new experience—and it keeps you outside Jefferson County as requested.
From Charles Town, drive about 20–25 minutes up to the
C&O Canal National Historical Park access near
Sandy Hook, MD, in Washington County.
Once you’re there, you can:
- Walk or bike along the C&O Canal towpath with views of the river and cliffs.
- Cross the pedestrian bridge over to lower Harpers Ferry for food or photos (optional side step).
- Watch kayakers and rafters from the Maryland shore.
If you enjoy rivers and easy, flat walks, this is a simple way to get outside for a few hours. The towpath is especially nice in spring and fall, when the leaves and light make the whole area glow.
4. Berryville, VA – Small-Town Charm in Clarke County
About 25–30 minutes south of Charles Town sits
Berryville, the county seat of
Clarke County, Virginia. It’s one of those classic small towns that looks like it came right out of a movie.
Downtown Berryville is compact and walkable. You can:
- Stroll along Main Street and browse local shops.
- Stop in a local café or bakery for coffee and a treat.
- Check out seasonal events, like markets or small festivals, if your timing is right.
Berryville is perfect when you just want a
gentle, easy day trip without a jam-packed schedule. It pairs nicely with a scenic drive through Clarke County’s rolling countryside—especially if you enjoy barns, pastures, and winding backroads.
5. Shenandoah River & Country Roads in Clarke County, VA
Clarke County isn’t just about Berryville. If you love peaceful drives and river views, this area is made for you.
From Charles Town, head south and explore:
- Pull-offs and river access points along the Shenandoah River (check local maps for public access areas).
- Quiet backroads lined with horse farms, old stone walls, and mountain views.
- Seasonal farm stands that pop up with fresh produce, especially in summer and early fall.
Think of this as your
“no schedule” road trip. Just fill up the gas tank, turn on some music, and wander. If you’ve ever wanted to test out that new camera or just get away from screens, this kind of drive can feel surprisingly refreshing.
6. Winchester, VA – Historic Old Town in Frederick County
Head about 35–45 minutes southwest from Charles Town and you’ll reach
Winchester in Frederick County, Virginia. This small city packs in a lot—history, food, shopping, and year-round events.
The star of the show is
Old Town Winchester, a walkable downtown area with a pedestrian mall.
- Visit the pedestrian walking mall lined with restaurants and shops.
- Grab a seat at a patio café and people-watch.
- Explore local history museums or check out live music if you’re there on the right night.
Winchester is great for a
date day, family outing, or friends’ meetup. It feels big enough to keep you busy, but not so big that it’s stressful to navigate.
7. Museum of the Shenandoah Valley – Art, History & Gardens (Frederick County, VA)
Also in Frederick County, just a short hop from Old Town Winchester, is the
Museum of the Shenandoah Valley. If you like art, history, or gardens, you’ll probably want to carve out a few hours for this place.
Here’s what you can do:
- Walk through the formal gardens, which feel especially magical in spring and early summer.
- Explore exhibits that tell the story of the Shenandoah Valley.
- Check out any temporary exhibitions (they rotate often).
It’s a nice mix of indoor and outdoor time, so you can adjust depending on the weather. On a sunny day, wandering the gardens can feel like stepping into a postcard.
8. Leesburg, VA – Lively Historic Downtown in Loudoun County
Drive about 40–50 minutes east from Charles Town and you’ll hit
Leesburg in Loudoun County, Virginia. This town blends history with a modern, energetic vibe.
Downtown Leesburg is walkable and full of options:
- Stroll through the historic district with its brick sidewalks and old buildings.
- Try one of the many local restaurants, coffee shops, or ice cream spots.
- Browse antique stores, boutiques, and local gift shops.
If you enjoy places that feel both old and new at the same time, Leesburg delivers. You can spend a few hours or a full day here and never get bored.
9. Loudoun County Wine & Countryside Drives (Loudoun County, VA)
Loudoun County is known for its beautiful countryside and many
wineries and breweries. Even if you’re not a wine person, the views alone are worth the drive.
From Charles Town, you can be in the heart of Loudoun’s wine country in about 30–45 minutes.
On this kind of trip, you might:
- Pick one or two wineries or farm breweries with good views.
- Sit outside with a drink (or a non-alcoholic option) and enjoy the Blue Ridge Mountain scenery.
- Drive quiet backroads lined with vineyards, farms, and old stone fences.
If you’re planning a special day—maybe a birthday, anniversary, or just a break from routine—Loudoun’s countryside is an easy, memorable choice.
10. Martinsburg, WV – Small City Energy in Berkeley County
Just 25–30 minutes northwest of Charles Town is
Martinsburg, in neighboring Berkeley County, West Virginia. It’s close, convenient, and full of ways to spend an afternoon.
Martinsburg offers:
- A walkable historic downtown with local shops and restaurants.
- Railroad history and old architecture to explore from the outside or via tours and visitor centers.
- Seasonal events and festivals that bring the streets to life.
If you want something that feels familiar yet “different enough” from home, Martinsburg is a solid go-to. It’s especially nice if you don’t want to drive too far but still want to say you “went somewhere.”
Bonus: Outdoor Time in Berkeley County, WV
While you’re in Berkeley County, consider adding a little outdoor time to your road trip. Look for:
- Nearby parks and green spaces for short walks.
- Scenic overlooks and backroads with mountain or valley views.
- Local farm markets, especially in late summer and fall.
Sometimes the best memories come from unplanned stops—a roadside stand, a small park you’ve never heard of, or a viewpoint that doesn’t even have a name on the map.
Tips for Planning Your Charles Town Road Trips
To make the most of these
short road trips from Charles Town, WV:
- Check drive times before you go; most of these are within about an hour.
- Plan around the weather: choose museums for rainy days and hikes or gardens for sunny ones.
- Look up hours for museums, wineries, and shops—they can vary by season.
- Bring a small day bag with water, snacks, and a light jacket.
Think of Charles Town as your home base and these nearby counties—Washington (MD), Clarke (VA), Frederick (VA), Loudoun (VA), and Berkeley (WV)—as your playground.
What’s Your Favorite Day Trip From Charles Town?
Now it’s your turn.
Have you taken any of these
out-of-county road trips from Charles Town?
Did I miss a spot in
Washington, Clarke, Frederick, Loudoun, or Berkeley County that you absolutely love?
- Share your favorite nearby getaway in the comments.
- Tell us your best day trip story—funny mishaps, hidden gems, or perfect picnic spots.
- If you found this guide helpful, send it to a friend who’s planning a visit to Charles Town or the Eastern Panhandle.
Your ideas help other travelers discover new adventures—so don’t be shy. Drop a comment and share this post with anyone who loves a good road trip.
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