10 Fun Things To Do Near Charles Town, West Virginia (Jefferson County)
If you’re looking for a laid-back getaway with history, small-town charm, and easy outdoor adventures,
Charles Town, West Virginia is a smart pick. Tucked in
Jefferson County, just about an hour and a half from Washington, DC and Baltimore, this little city punches way above its weight when it comes to things to do.
Whether you love history, live music, good food, or just a quiet weekend in the mountains, you’ll find something around Charles Town that fits.
Below are
10 fun things to do near Charles Town to help you plan your trip.
1. Try Your Luck at Hollywood Casino at Charles Town Races
Let’s be honest: for many visitors, the first stop in Charles Town is the
Hollywood Casino at Charles Town Races.
This large casino and racing complex is just outside downtown and offers:
- Thoroughbred horse racing on a beautiful outdoor track
- Slots, table games, and poker
- On-site restaurants and bars
- Live entertainment and events
Even if you’re not a big gambler, it can be fun to watch the horses thunder down the track on a cool evening. Grab a drink, sit in the stands, and just enjoy the energy of race night.
Tip: If you’re visiting on a weekend, check the racing schedule and any concert listings ahead of time. Weekends can be busy, but they also have the most going on.
2. Walk Through History in Downtown Charles Town
Charles Town has deep roots. It was actually founded by
Charles Washington, George Washington’s younger brother, in the late 1700s. You’ll feel that history as soon as you step into the small but charming downtown.
Take a slow stroll and look for:
- Historic brick buildings and old storefronts
- Local restaurants and coffee shops
- Antique stores and small boutiques
- Murals and plaques telling the town’s story
Downtown isn’t huge, which is part of its appeal. You can easily walk it in under an hour, but you may end up spending a lot longer if you stop in for coffee, ice cream, or a local craft beer.
If you like to mix sightseeing with food, plan your walk around lunch or dinner and try a locally owned spot instead of a chain.
3. Tour the Jefferson County Courthouse & John Brown History Sites
Charles Town played a key role in the lead-up to the Civil War. In 1859, the famous abolitionist
John Brown was tried here after his raid on Harpers Ferry.
The
Jefferson County Courthouse in downtown Charles Town is where his trial took place. The building you see now dates from the late 1800s, but it stands on that historic site.
Nearby, you’ll find:
- Historical markers describing John Brown’s trial
- Walking routes that link related sites in Charles Town and Harpers Ferry
If you’re a history buff, it’s powerful to stand on the same ground where events that helped spark the Civil War unfolded. Even if you only know the basics from school, it’s worth a stop.
4. Step Inside the Charles Washington Hall & Washington Heritage Sites
To really understand Charles Town, you need to meet the family it’s named after. The city has strong connections to the Washingtons, and you can still see those ties today.
Key spots to check out:
- Charles Washington Hall – A historic building in the center of town, now used for events and community gatherings.
- Markers and exhibits related to the Washington family in Charles Town and nearby Kearneysville and Summit Point.
While this isn’t a huge museum-style attraction, it’s a great place to pause, read the displays, and get a feel for what life was like here in the 1700s and 1800s.
If you enjoy American history but don’t want a long, formal tour, this is a relaxed way to learn a bit as you explore.
5. Take a Day Trip to Harpers Ferry National Historical Park
Just a short drive from Charles Town—usually around 10–15 minutes depending on where you start—you’ll find one of West Virginia’s most famous destinations:
Harpers Ferry National Historical Park.
This is an easy and rewarding day trip. Harpers Ferry offers:
- A historic lower town with 1800s-style buildings
- Beautiful views where the Potomac and Shenandoah Rivers meet
- Short hikes with big payoffs, like sections of the Appalachian Trail
- Small museums and historical exhibits
If you only have time for one hike, many people choose the overlook at
Maryland Heights. It’s steep in places and will get your heart pumping, but the view of Harpers Ferry from above is incredible.
Visiting Harpers Ferry is one of the top things to do near Charles Town, especially if you want a mix of nature and history in one place.
6. Float, Paddle, or Play on the Rivers
When the weather warms up, the rivers around Charles Town become one big playground. The
Shenandoah and
Potomac Rivers are close by, and there are several outfitters in the area that can help you get on the water.
Popular river activities include:
- River tubing – Float down the river in an inner tube. Perfect on a hot summer day.
- Kayaking or canoeing – A bit more active, great for couples or families with older kids.
- Rafting – Some sections offer mild whitewater fun, often suitable for beginners.
You don’t have to be an expert to enjoy any of this. Many companies provide life jackets, gear, and shuttle service. You just show up with a swimsuit, water shoes, and maybe a waterproof bag for snacks.
If you’re planning a summer weekend in Charles Town, booking a river trip can be the highlight of your visit.
7. Explore the Back Roads on a Scenic Drive
One of the easiest—and often most overlooked—things to do near Charles Town is simply going for a drive.
Jefferson County sits where West Virginia, Maryland, and Virginia meet, so you have lots of options within a short radius. As you wander, you’ll see:
- Rolling farms and old barns
- Mountain ridges in the distance
- Quiet country churches and old cemeteries
- Small towns like Shepherdstown and Harpers Ferry
Fall is especially beautiful, with colorful leaves covering the hillsides. But even in winter, the bare trees and open fields have a peaceful feel.
A simple idea: grab coffee in downtown Charles Town, plug in a loose route on your GPS, and take your time following the back roads. Stop whenever a view or little roadside spot catches your eye.
8. Taste Local Flavors at Wineries, Breweries, and Farm Markets
The area around Charles Town is part of a wider Shenandoah Valley food and drink scene. You’ll find:
- Wineries tucked into the hills, often with outdoor seating and live music
- Breweries and taprooms serving craft beer
- Farm markets with local produce, treats, and handmade items
While offerings change over time, it’s worth searching for:
- “Wineries near Charles Town WV”
- “Breweries near Charles Town WV”
- “Jefferson County WV farm markets”
If you’re traveling with friends, you can easily build a relaxed afternoon around tastings and small bites. Just be sure to plan a safe ride—designate a driver or use a ride service if it’s available.
9. Hike, Bike, or Birdwatch in Jefferson County
You don’t have to be hardcore to enjoy the outdoors near Charles Town. There are plenty of shorter, easy-to-moderate walks and rides.
Ideas to consider in Jefferson County and nearby:
- Canal paths and riverside trails near Harpers Ferry and along the Potomac
- Wooded trails that are great for birdwatching and photography
- Country roads that many cyclists use for scenic bike rides
Pack comfortable shoes, a refillable water bottle, and a light jacket if you’re heading out in spring or fall. Even a one- or two-mile walk can help you slow down and really appreciate the quieter side of West Virginia.
If you’re from a big city, the silence and fresh air might be the thing you remember most from your trip.
10. Catch Local Events, Fairs, and Festivals
Charles Town and Jefferson County host various
seasonal events throughout the year. These can add a fun local flavor to your visit.
Depending on when you go, you might find:
- Street festivals and live music in downtown Charles Town
- Holiday parades or tree-lighting events
- County fairs with rides, food, and livestock shows
- Farm or harvest festivals in the fall
Before your trip, search for terms like:
- “Charles Town WV events this weekend”
- “Jefferson County WV festivals”
You may stumble onto a small-town event that ends up being the highlight of your stay—think funnel cake, local bands, and friendly conversations with people who live here.
Planning Your Charles Town, West Virginia Getaway
What makes
Charles Town special isn’t just one big attraction. It’s the mix of things to do within a short drive:
- Casino nights and horse racing
- Quiet historic streets and Washington family history
- Rivers to float and trails to hike
- Nearby Harpers Ferry and scenic country drives
If you’re coming from DC, Baltimore, or Northern Virginia, Charles Town works well as:
- A quick weekend escape
- A day trip with a mix of history and outdoor time
- A base for exploring more of the Eastern Panhandle of West Virginia
Share Your Charles Town Experience
Have you been to
Charles Town, West Virginia or anywhere else in
Jefferson County?
- Which places did you love most?
- Did you find a great hike, a favorite restaurant, or a hidden-viewpoint?
Drop a comment with your tips and stories—your experience can help other travelers plan their own trip.
And if you found this list of
10 things to do near Charles Town helpful, go ahead and
share it with a friend who’s looking for a new weekend getaway idea.
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