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flowersflowers

Things To Do

Marker Miller Orchard

3035 Cedar Creek Grade, Winchester, VA 22602
, (540) 662-1396

A seasonal favorite offering fresh cider, baked goods, and a quintessential fall atmosphere.

Old Town Winchester

Loudoun St Walking Mall, Winchester, VA 22601
, (540) 535-3356

A walkable historic district with curated shops, cafés, and restaurants—ideal for a leisurely afternoon.

Bright Box Theatre

15 N Loudoun St, Winchester, VA 22601
, (540) 313-0622

An intimate venue in the heart of downtown featuring live music, comedy, and select weekend events.

The Salamander Spa and Resort

500 North Pendleton Street, Middleburg, VA 20117

Salamander Resort & Spa is a stunning luxury resort located in the heart of Middleburg’s horse country. Surrounded by rolling hills and beautiful fall scenery, it’s the perfect place for guests looking to relax and indulge. The resort offers a full-service spa, fine dining, and breathtaking views, making it ideal for a special outing or a full day of pampering.

Historic Route 11 Drive-In Theatre

5890 Valley Pike, Stephens City, VA 22655
, (540) 665-6982

A classic drive-in experience just outside the city—perfect for a quiet, nostalgic evening.

Glen Burnie Gardens

901 Amherst St., Winchester, VA

A beautifully landscaped garden with winding paths, vibrant flowers, and peaceful views—perfect for a relaxing stroll just minutes from downtown Winchester.

Shenandoah National Park

Skyline Drive Entrance, Front Royal, VA 22630
, (540) 999-3500

A scenic escape just outside the city, known for mountain views, fall foliage, and peaceful drives along Skyline Drive. Ideal for a relaxed outing or light adventure.

Skyline Drive

17157 Skyline Drive, Front Royal, VA 22630
, (540) 999-3500

A scenic mountain drive known for sweeping views of the Shenandoah Valley and beautiful fall foliage. Perfect for a relaxed drive with scenic overlooks just outside Winchester.

Apple Blossom Mall

1850 Apple Blossom Drive, Winchester, VA 22601

The main indoor shopping mall in Winchester with a mix of popular stores, a food court, and a movie theater—perfect if guests want an easy, all-in-one shopping stop.

Leesburg Premium Outlets

241 Fort Evans Road Northeast, Leesburg, VA 20176
, (703) 737-3071

Located about 45–50 minutes from Winchester, this outlet destination features over 100 designer and name-brand stores—perfect for a polished shopping experience just outside the city.

The Ritual Spa Winchester, VA

103 East Piccadilly Street, Winchester, VA 22601
, (540) 326-3023

A cozy, boutique-style spa in downtown Winchester known for personalized massages and facials in a calming, intimate setting—great for a relaxing, elevated experience.

James Charles Winery & Vineyard

4063 Middle Road, Winchester, VA 22602
, (540) 931-1700

Approximately 10 minutes from Stephens City, this local winery offers tastings in a quiet, scenic setting—ideal for a laid-back afternoon.