Things to do in Shepherdstown

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A street lined with brick buildings, including a bank and a restaurant.
A historic street with red brick buildings, a church steeple, and a sign for a local shop.
A street with a red brick building, a sign for Maria's Taco, and a sign for Grapes & Grains Gourmet.
A row of bicycles parked against a metal bike rack on a city street.
A vintage storefront with a sign reading "Open Soon... Pop on in!" and a vintage suitcase.

Things to do

South Mountain Private Battlefield Tour

South Mountain Private Battlefield Tour

$120
per traveler
South Mountain Private Battlefield Tour
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What to do in Shepherdstown

 

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Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/10 (1 review)
This intimate historic theater hosts diverse performances from indie films to live music in a beautifully preserved setting. Arrive early to enjoy Shepherdstown's dining scene before your show.
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Popular day trips from Shepherdstown

A river with a bridge, surrounded by dense greenery and a town with buildings and a church.

Harpers Ferry

A statue on a pedestal surrounded by a fence, with a misty background and trees.

Sharpsburg

A street lined with brick buildings, including a pharmacy and a restaurant.

Martinsburg

An aerial view of a town with a river, dense trees, and various buildings.

Kearneysville

A stone tower with a flagpole and an American flag.

Boonsboro

Frequently asked questions

Is Shepherdstown worth visiting?
From shopping to outdoor adventures and history, there are loads of fun things to do in Shepherdstown. Be sure to experience the area's blend of awesome sights, culture and local charm.
How do I spend a day in Shepherdstown?
Crystal Grottoes Caverns and Bolivar Heights Scenic Overlook are two great places to kick-start your vacation adventures. Be sure to explore the retail and dining options in Shepherdstown while you're here too.
What is the top tourist attraction in Shepherdstown?
Harpers Ferry National Historical Park is one of the top tourist attractions in Shepherdstown and deserves a place on every itinerary of the area.
Is three days enough to stay in Shepherdstown?
Three days will be enough time to check out many city sights, including Antietam National Battlefield, Shepherdstown Museum and Shepherdstown Opera House. The average stay in Shepherdstown is three days. If you feel the urge to extend your adventure, Loudoun County isn't far away.
What are some activities to do in Shepherdstown with kids?
Whether you're vacationing with young explorers or adventure-seeking teens, an itinerary filled with fun activities is the key to a stress-free getaway. Check out our ideas for what to do in Shepherdstown with kids.

What to do in Shepherdstown for adults?
There are lots of things to do in Shepherdstown, with activities for adults of all ages. End the day with a visit to Big Cork Vineyards or Antietam National Cemetery.
Are there free things to do in Shepherdstown?
From relaxing in parks to wandering around exciting neighborhoods, it's simple to discover free things to do in Shepherdstown. If you need inspiration, ask a local tour guide for some tips. Morgan's Grove Park is a great spot for anyone planning to save on their sightseeing adventures.