Wine Tasting at Valerie Hill Vineyard & Winery

Indulge in a romantic evening of wine tasting at Valerie Hill Vineyard & Winery. Located in a historic plantation home, this winery offers a picturesque setting for you and your partner to enjoy a variety of wines. Sip on local favorites while taking in the beautiful views of the vineyard. Alternative options: James Charles Winery, Veramar Vineyard.

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Dinner at The Union Jack Pub & Restaurant

Enjoy a delicious meal at The Union Jack Pub & Restaurant, a cozy British-style eatery in downtown Winchester. With a menu featuring classic British dishes and a warm, inviting atmosphere, this restaurant is the perfect spot for a relaxing date night. Alternative options: Village Square Restaurant, Roma Wood-Fired Pizzeria.

Stroll Through Old Town Winchester

Take a leisurely stroll through Old Town Winchester and explore the charming shops, art galleries, and historic sites. With its cobblestone streets and beautifully preserved architecture, Old Town Winchester is the ideal setting for a romantic evening out. Alternative options: Abrams Delight Museum, Old Town Walking Mall.

Catch a Show at the Bright Box Theater

Experience live entertainment at the Bright Box Theater, a popular venue in downtown Winchester. From comedy shows to live music performances, the Bright Box Theater offers a diverse range of events for you and your partner to enjoy. Alternative options: Shennadoah University Conservatory of Music, Winchester Little Theatre.

Visit the Handi Spot Pottery Painting Studio

Get creative together at the Handi Spot Pottery Painting Studio, where you can paint your own pottery pieces to take home as unique mementos of your date night. Unleash your artistic talents and enjoy a relaxing and fun-filled evening at this charming studio. Alternative options: Make Nest Studio, Pottery on the Wheel.

Take a Cooking Class at Nibblins

Learn new culinary skills together by taking a cooking class at Nibblins, a gourmet kitchen store in downtown Winchester. From pasta-making workshops to wine pairing classes, Nibblins offers a variety of cooking classes for foodies of all skill levels. Alternative options: Bon Vivant Cooking School, Taste Buds Kitchen.

Relax at the Shenandoah Valley Hot Yoga Studio

Unwind and de-stress with a hot yoga session at the Shenandoah Valley Hot Yoga Studio. This serene studio offers a range of yoga classes for all levels, providing the perfect opportunity for you and your partner to relax and rejuvenate together. Alternative options: Blue Ridge Yoga, The Yoga Studio.

Play Mini Golf at Magic Putting Place

Have a playful and lighthearted date night at Magic Putting Place, where you can challenge each other to a round of mini golf. With its whimsical and colorful course, Magic Putting Place is sure to add some fun and laughter to your evening. Alternative options: Shenandoah Valley Golf Club, Rock Harbor Golf Course.

Enjoy a Couples Massage at Rejuvenating Massage

Treat yourselves to a pampering couples massage at Rejuvenating Massage, a tranquil spa in Winchester. Relax and unwind together as skilled massage therapists work their magic to melt away your stress and tension. Alternative options: A Touch of Health, Winchester Wellness Centre.

Attend a Paint & Sip Night at Muse Vineyards

Get creative and enjoy some wine at the same time by attending a paint & sip night at Muse Vineyards. With a glass of wine in hand, you and your partner can follow along with an instructor to create your own masterpiece. Alternative options: Beyond the Pallet, Shenandoah Paint and Sip.

So why wait? Plan your next date night in Winchester, VA and let Wyndy help you find the perfect sitter to take care of your little ones while you enjoy a well-deserved night out with your partner. Book a trusted and experienced sitter on Wyndy.com and embark on a memorable date night in Winchester today!