Mountain Mama Vacation Homes

A Traveler’s Guide to Charles Town, WV

While you enjoy the nature and historical attractions in Harpers Ferry, visiting Charles Town, WV, will give you much more context to the area’s history—and a charming town worth exploring during your stay!

Charles Town is the county seat and is famous for being the site of the John Brown trial after his raid on Harpers Ferry and the wartime history of soldiers occupying the town due to the armory location in Harpers Ferry.

It’s located less than 10 miles west of the Shenandoah and Potomac River confluence at Harpers Ferry. That’s a short drive to a town that formed its unique identity with historical sites and a charming main street filled with shops, dining, and more.

Use this guide to plan a day trip to explore Charles Town after you check into your Mountain Mama vacation home or cabin!

A Quick History of Charles Town

Photo Credit: George Sheldon

Did you know that the first President of the United States had siblings? Born in 1738, Charles Washington was George Washington’s youngest brother and would become the founder of Charles Town thanks to substantial land inheritance in present-day Jefferson County.

Charles Washington originally moved to the area in 1780, where he built Happy Retreat to live. Over his remaining years, he donated and sold land near this residence to create the town. Although he died just 12 years after the city of Charles Town was officially established by the Virginia General Assembly, it continued to grow and preserve Mr. Washington’s legacy.

As one of the earliest towns in the United States, it endured several pivotal moments in history that are still evident today. It was the site of military occupancy during the Civil War, with many artifacts preserved in the Jefferson County Museum. It hosted the infamous Virginia v. John Brown trial in the Jefferson County Courthouse. It’s even part of the 136-mile-long Washington Heritage Trail, which includes the Harpers Ferry National Historical Park.

While visiting Charles Town, note the streets named after Washington’s brothers and wife.

Best Things to Do in Charles Town, WV

Tour Historical Sites

Photo Credit: George Sheldon

Discover the original buildings and notable sites that made Charles Town what it is today. Stand in the historic downtown center where the first plots of land were donated by Charles himself to found his namesake town, like the sites of the Jefferson County Courthouse, City Hall, and the post office (originally the jailhouse). Tour Charles Washington’s former house at Happy Retreat and even his office, where he sold plots of land to create the town.

Take a walking tour to see historical markers around town highlighting events like the hanging of abolitionist John Brown for his attempt to raid Harpers Ferry in 1859 and the birthplace of Major Martin Delany, a free African-American who served during the Civil War.

Explore Shops on Main Street

Photo Credit: via Google Images CCL

The present blends seamlessly with the past when exploring Main Street in the historical downtown district. Stroll Washington Street for selfies in front of the colorful mosaic art mural, shopping local knick-knacks in charming boutiques and tons of eateries.

Grab a drink at the Abolitionist Ale Works, browse vintage records in the Fuzzy Dog Books & Music, support local vendors in the Needful Things Emporium, and check out the art inside the Firehouse Gallery.

Contemplate History in the Jefferson County Museum

Photo Credit: Picryl via Google Images CCL

Charles Town itself feels like a walk through living history. The Jefferson County Museum takes you back even further in time with more than 2,500 objects on display, retelling the town’s rich history.

Linger around the displays of aged black and white photos showing what the town looked like centuries ago. Trace your steps with vintage maps revealing the original layout of the town. See donated uniforms used from the Civil War and World Wars. Even get a peek into the lifestyles of the town’s first settlers with various household goods, and children’s toys passed down from generations.

Get Lucky at the Hollywood Casino

Photo Credit: refrina

Luck strikes at any hour, and the Hollywood Casino at Charles Town Races is always open! Anytime you’re feeling luck on your side, make the short drive to this exhilarating entertainment complex.

You can win big with more than 1,900 slot machines, try your hand at poker and blackjack, or bet on your favorite number in roulette.

This isn’t your typical Las Vegas-style casino. The thoroughbred horse races are one of the casino’s most popular attractions, with championship steeds and high stakes available.

Enjoy Leisure and Recreation

Get outside Harpers Ferry and enjoy some of the other fun recreational activities near Charles Town. There’s something to do for all ages in every season!

Experience local live entertainment with plays at the Old Opera House Theatre and jam out at the Event Center at Hollywood Casino. For outdoors lovers, explore the hiking trails at the Cool Spring Preserve and get in a round of golf at the Locust Hill Golf Course, rated top five in the state with views of the Blue Ridge Mountains.

Set your calendars for the annual Jefferson County Fair and WV Fest.

Where to Eat in Charles Town

Photo Credit: George Sheldon

Craving some delicious eats during your cabin stay in Harpers Ferry? Downtown Charles Town is a short drive away and filled with tasty eateries. Check out some of our favorite local restaurants for local and international flavors. On Saturday mornings, don’t forget to sample fresh produce from the local farmer’s market to prepare a home-cooked meal.

Oretaga’s Taco Shop

In the mood for tacos and other Mexican favorites? You’ll love Oretaga’s Taco Shop.

Abolitionist Ale Works

Abolitionist-inspired brewery serving barrel-aged beer and artisan pizza.

Grandma’s Diner

Traditional diner serving American and Mexican dishes with breakfast available all day.

Sumittra Thai Cuisine

  • Address: 213 W Washington St, Charles Town, WV
  • Website:
  • Price: $$

A stylish restaurant specializing in authentic Thai dishes.

The Caverns Ice Cream

Treat yourself to a delicious sandwich or sundae made with their signature hand-dipped ice cream.

Alfredo’s Mediterranean Grill & Steakhouse

Made-to-order Mediterranean cuisine is served in a casual dining venue that hosts live music on select nights.

Charles Town Farmers’ Market

The seasonal farmers’ market is held weekly on Saturday mornings, starting in the spring, with local vendors, live music, and kid-friendly activities.

Where to Stay Near Charles Town

Visitors to Charles Town can find luxurious cabin accommodations in Harpers Ferry. It lets you enjoy the stunning natural surroundings of the Blue Ridge Mountains and rivers while being just a short drive away from popular day trips to Charles Town and Washington, D.C.

Choose Mountain Mama vacation homes and cabins for your next stay in West Virginia!


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