Middleburg VirginiaATTRACTIONS & THINGS TO DO
Listed below are the best attractions and things to do near Middleburg, Virginia.
1. Boxwood Estate Winery
BOUTIQUE WINE DESTINATION
Boxwood Estate Winery is a celebrated boutique winery located in the heart of Middleburg's wine country. It offers wine tastings, vineyard tours, and an exclusive wine club, all set on a picturesque estate. Visitors enjoy the refined ambiance and acclaimed Bordeaux-style wines produced on site.
2. Lost Barrel Brewing
FAMILY-FRIENDLY BREWERY
Lost Barrel Brewing is a vibrant brewery situated on a spacious horse farm, offering craft beer and beautiful views. The brewery prides itself on its welcoming, family-owned atmosphere, with ample indoor and outdoor seating. Guests can enjoy local brews, live music, and community events throughout the year.
3. Greenhill Winery & Vineyards
SCENIC VINEYARD EXPERIENCE
Greenhill Winery & Vineyards is renowned for its boutique wines and scenic farm winery setting in Loudoun County. Visitors are treated to wine tastings in an elegant environment with sweeping views of the countryside. The winery's focus on quality and hospitality makes it a favorite destination for wine lovers.
4. National Sporting Library & Museum
EQUESTRIAN HERITAGE MUSEUM
The National Sporting Library & Museum preserves and promotes Virginia's equestrian and field sports traditions. Located on a six-acre campus, it features rare books, art exhibits, and artifacts related to riding, foxhunting, and more. It serves as a cultural center for sporting history and outdoor pursuits.
5. 50 West Vineyards
COUNTRYSIDE WINE RETREAT
50 West Vineyards is nestled amid rolling hills, offering a tranquil escape with its panoramic views and estate-grown wines. The vineyard is known for its inviting tasting room and exceptional wine selections. Guests can relax on the terrace while sampling signature wines and enjoying the scenery.
6. Chrysalis Vineyards at The Ag District
INNOVATIVE LOCAL WINERY
Chrysalis Vineyards is notable for its dedication to producing unique varietals, including Norton, America's native grape. Set within the Ag District, the winery presents guided tastings, farm-to-table experiences, and scenic views. Its commitment to agricultural innovation draws wine enthusiasts from the region.
7. Gallery on Madison
LOCAL ART SHOWCASE
Gallery on Madison exhibits a curated selection of local and regional art, from contemporary paintings to fine crafts. The gallery offers visitors an opportunity to explore the area's creative spirit and purchase unique works. Rotating exhibits and artist events make it a cultural highlight in downtown Middleburg.
8. Glenwood Park
EQUESTRIAN EVENT VENUE
Glenwood Park is famous for hosting renowned equestrian and outdoor events, including steeplechase races and country fairs. The park features expansive grounds, making it a popular destination for horse enthusiasts and families alike. Its legacy as a sporting venue ties into Middleburg's deep equestrian roots.
9. Middleburg Historic District
CHARMING DOWNTOWN STROLL
The Middleburg Historic District is defined by its quaint streets lined with 18th and 19th-century architecture, boutique shops, and inviting cafes. Visitors can explore over 160 buildings listed on the National Register of Historic Places. The district blends historic charm with vibrant shopping and dining opportunities.
10. Red Fox Inn & Tavern
HISTORIC DINING LANDMARK
Red Fox Inn & Tavern, established in 1728, stands as one of America's oldest continually operating inns. The restaurant is acclaimed for its classic American fare served in an atmosphere rich with colonial history. Guests appreciate its period décor, cozy fireplaces, and storied hospitality.
11. The Upper Crust
POPULAR PASTRY SHOP
The Upper Crust bakery is beloved for its homemade pies, pastries, and comforting soups in a casual café setting. Locals and visitors alike flock here for freshly baked goods and friendly service. It's a perfect spot for a snack or a light lunch while exploring downtown.
12. Finch Middleburg
TRENDY BOUTIQUE SHOPPING
Finch Middleburg offers a modern boutique shopping experience with a curated selection of clothing, accessories, and home goods. The store is known for its stylish atmosphere and attentive service. Shoppers can discover unique fashion finds and gifts in the heart of Middleburg.
13. Cana Vineyards & Winery of Middleburg
FAMILY-FRIENDLY VINEYARD
Cana Vineyards & Winery offers a welcoming atmosphere for families and groups, with picnic areas, live music, and diverse wine selections. Set on a hill with panoramic views, it's ideal for casual wine tastings and social gatherings. The vineyard has become a staple for visitors seeking relaxation and local wines.
14. Aldie Mill Historic Park
HISTORIC GRISTMILL SITE
Aldie Mill Historic Park, just outside Middleburg, features a fully restored 19th-century gristmill surrounded by picturesque grounds. Guided tours share the site's industrial history and demonstrate traditional milling. The park offers insight into the region's agricultural past and hosts seasonal events.
15. The Red Horse Tavern
LOCAL PUB FAVORITE
The Red Horse Tavern is a casual pub known for its lively atmosphere, diverse menu, and regular live music. Patrons enjoy classic American fare and a selection of local beers in a relaxed setting. It's a popular gathering place for both locals and visitors seeking a taste of small-town hospitality.