Wine Tasting at Shepherdstown’s Local Winery

Indulge in a romantic evening of wine tasting at Shepherdstown’s local winery. Sip on delicious wines while enjoying the picturesque vineyard views with your significant other. Spending time together in a serene setting can be the perfect way to relax and unwind.

Alternative options: Big Cork Vineyards, Elk Run Vineyards, Rock Hill Plantation Winery

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Dinner and a Show at the Black Box Arts Center

Combine dinner and entertainment by attending a show at the Black Box Arts Center in Shepherdstown. Enjoy a delicious meal at a nearby restaurant before heading to the theater for a live performance. This unique date night idea is sure to create lasting memories for you and your partner.

Alternative options: Apollo Civic Theatre, Old Opera House, Wonderment Theatre

Stroll Through Historic Downtown Shepherdstown

Take a leisurely stroll through the historic streets of downtown Shepherdstown. Explore the quaint shops, art galleries, and charming cafes hand in hand with your loved one. The old-world charm of the town makes it the perfect backdrop for a romantic evening out.

Alternative options: Harpers Ferry National Historical Park, Antietam National Battlefield, Charles Town

Couples Massage at a Local Spa

Pamper yourselves with a relaxing couples massage at a local spa in Shepherdstown. Unwind together as you enjoy a soothing massage in a tranquil setting. This intimate experience is a great way to bond with your partner and de-stress from the daily grind.

Alternative options: Balancing River Spa, The Spa at Turf Valley, The Apothecary at Gilded Thistle

Take a Sunset River Cruise on the Potomac

Embark on a romantic sunset river cruise on the Potomac River. Enjoy breathtaking views of the water and sky as you cruise along with your partner. The peaceful serenity of the river at dusk creates a magical atmosphere that is perfect for a date night.

Alternative options: River & Trail Outfitters, River Riders, Harpers Ferry Adventure Center

Attend a Live Music Performance at the Shepherdstown Opera House

Spend an evening grooving to live music at the Shepherdstown Opera House. Check out the schedule for upcoming performances and enjoy a night of music and dancing with your significant other. The lively atmosphere and great music make for a fun and entertaining date night.

Alternative options: Purple Fiddle, Gypsy Sally’s, Bright Box Theater

Try a Cooking Class Together at a Local Culinary School

Get hands-on in the kitchen by taking a cooking class together at a local culinary school in Shepherdstown. Learn new recipes and culinary techniques while bonding with your partner over delicious food. Cooking together can be a fun and interactive date night activity that you both will enjoy.

Alternative options: Cooking Studio of Downtown Shepherdstown, Kitchen Studio Cooking School, Sur La Table – Alexandria

Visit the George Tyler Moore Center for the Study of the Civil War

Explore the history of the Civil War by visiting the George Tyler Moore Center in Shepherdstown. Take a guided tour of the museum and learn about the local impact of this pivotal period in American history. Engaging in educational activities together can be a unique and enriching experience for you and your partner.

Alternative options: Harpers Ferry National Historical Park, Antietam National Battlefield, Pry House Field Hospital Museum

Enjoy a Romantic Picnic at Morgan’s Grove Park

Pack a picnic basket with your favorite foods and head to Morgan’s Grove Park for a romantic outdoor meal. Spread out a blanket, enjoy the scenic views, and savor each other’s company in a peaceful natural setting. A picnic in the park is a simple yet charming date night idea that allows you to connect with nature and each other.

Alternative options: Jefferson County Memorial Park, Yankauer Nature Preserve, Shepherdstown Riverfront Park

Take a Hike at the C&O Canal National Historical Park

Get active and explore the great outdoors by taking a hike at the C&O Canal National Historical Park. Choose a scenic trail to hike with your partner and enjoy the beauty of nature together. Spending time outdoors can be a refreshing and invigorating way to bond with your loved one on a date night.

Alternative options: Harpers Ferry National Historical Park, Loudoun Heights Trail, Maryland Heights Trail

Whether you’re looking for a relaxing evening or an adventurous outing, Shepherdstown offers a variety of date night activities for parents in need of a break. Take some time for yourselves and enjoy each other’s company in this charming town.

If you’re ready to plan your date night in Shepherdstown but need a trustworthy babysitter to watch the kids, consider using Wyndy. Simply book a sitter through the Wyndy app and enjoy peace of mind knowing your children are in good hands while you have a well-deserved night out with your partner.