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

￥19,194
per traveler
South Mountain Private Battlefield Tour
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What to do in Shepherdstown

Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/5 (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

Frequently asked questions

Is Shepherdstown worth visiting?
Shepherdstown offers a unique mix of local charm, culture and attractions. Whether you're into outdoor activities, history or regional cuisine, there's plenty to enjoy here.
How do I spend a day in Shepherdstown?
Crystal Grottoes Caverns and Bolivar Heights Scenic Overlook are two excellent places to start your getaway adventures. Remember to check out the retail and dining options in Shepherdstown while you're there too.
What is the top tourist attraction in Shepherdstown?
The top tourist attraction in Shepherdstown is Harpers Ferry National Historical Park, so don't forget to add it to your sightseeing list.
Is three days enough to stay in Shepherdstown?
You can easily visit top attractions like Antietam National Battlefield, Shepherdstown Museum and Shepherdstown Opera House with a three-day break in Shepherdstown. On average, many travelers book three days here. There's plenty to discover nearby too, so stay a while longer and head to Loudoun County.
What are some activities to do in Shepherdstown with kids?
Deciding what to do in Shepherdstown with kids is easier than ever. Whether you have teenagers or toddlers, there are lots of family-friendly activities to keep everyone busy here.

What to do in Shepherdstown for adults?
There's no shortage of things to do in Shepherdstown, with experiences 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 strolling around exciting neighborhoods, it's a breeze to discover free things to do in Shepherdstown. If you're stuck for ideas, ask a local tour guide for some tips. Morgan's Grove Park is a great spot for anyone wanting to save on their sightseeing activities.