Hillsboro, VA

868 Estate Vineyards is one of the premier wine destinations in the Hillsboro area, offering a full experience of wine, food, and nature. Set on 120 acres, the vineyard boasts sprawling views, a tasting room, and a gourmet restaurant onsite. Guests can enjoy award-winning wines paired with seasonal dishes in a relaxing, elegant atmosphere. The vineyard frequently hosts live music, art shows, wine education sessions, and outdoor festivals. There are walking trails around the property for those who wish to explore the grounds between tastings. Group bookings and private events like weddings or corporate outings are also common here. The friendly, knowledgeable staff enhances every visit with personalized recommendations. It’s a perfect weekend retreat for couples, friend groups, and wine lovers alike. Parking can be limited during peak hours, especially on event days, so arranging a ride ensures a smoother experience. For guests wanting a peaceful escape that also delights the palate, 868 delivers.

Set against a breathtaking mountain backdrop, Hillsborough Vineyards & Brewery is a dual-concept venue that caters to both wine and craft beer enthusiasts. Family-owned and operated, the venue offers a curated list of wines and small-batch beers crafted onsite. Guests can sip drinks from the patio, which overlooks acres of grapevines and lush Virginia landscape. Inside the stone farmhouse, the tasting bar offers an intimate experience, where staff walk visitors through each pour. The location is also known for its commitment to quality, with unique blends that reflect the terroir of the region. On weekends, food trucks and live acoustic music add to the relaxing ambiance. Visitors are welcome to bring a picnic or purchase snacks onsite. Events like seasonal dinners, yoga in the vineyard, and private parties are popular year-round. Whether you’re there to unwind or celebrate, this destination blends rustic charm with sophisticated flavor. Avoid the drive and arrive in comfort with a private ride service.

The Old Stone School is one of Hillsboro’s most iconic historic buildings and now functions as a vibrant cultural center. Built in 1874, the schoolhouse has been beautifully restored and now hosts concerts, community events, weddings, art exhibitions, and lectures. The large auditorium features wood floors, a stage, and elegant natural light, making it perfect for intimate gatherings or public events. The surrounding gardens and grounds add charm and space for outdoor functions. Local residents and out-of-town guests alike appreciate its role in keeping the town’s cultural spirit alive. The venue is home to many local traditions, including seasonal craft fairs and speaker series. Visitors can enjoy a unique blend of history and modern amenities in one location. The facility also offers flexible rental space for private events. Getting to and from events can be stress-free with timely transportation provided directly to its doors.