Greenhill Winery & Vineyards – Middleburg, VA

Greenhill Winery & Vineyards offers a premier wine tasting experience where visitors can savor a rotating selection of small-batch estate wines. Whether indoors in the contemporary farmhouse-style tasting room or outdoors overlooking the Blue Ridge Mountains, guests are treated to expertly guided flights of Virginia-grown varietals. Tastings typically include five wines, ranging from crisp whites to robust reds and sparkling options. Each selection is paired with a story — about the grape, the process, and the land — shared by knowledgeable wine associates. For those interested in deepening their appreciation, staff are happy to share pairing tips and food recommendations. Walk-ins are welcome, but reservations are encouraged, especially on weekends and holidays. The atmosphere is elegant yet welcoming, making it ideal for couples, small groups, and solo travelers alike. Guests can also pair their tastings with local cheese boards and charcuterie available on-site. Bottles are available for purchase to take the experience home.

The Private Tours & Cellar Experience at Greenhill Winery offers a more personalized and immersive adventure into Virginia wine. Guests begin with a guided walk through the estate’s scenic vineyards where they learn about varietals, vine care, and seasonal harvests. The tour continues into the winemaking facility and barrel room where the fermentation and aging process comes to life. Along the way, guests are introduced to the winemaker’s approach and Greenhill’s philosophy on minimal intervention and sustainability. The experience concludes with a seated tasting of exclusive reserve wines, often poured directly from the barrel. These wines are typically not available to the general public, offering a rare opportunity to savor something truly special. The setting is private, intimate, and perfect for couples or groups celebrating a special occasion. It’s a sensory journey through the artistry and science behind each bottle. Reservations are required for this premium service.

Greenhill Winery provides a magical setting for weddings, rehearsal dinners, corporate retreats, and milestone celebrations. With views of the mountains, a historic 1700s farmhouse, and rows of estate-grown vines, the property sets a stunning backdrop for both intimate and large gatherings. The venue includes indoor and outdoor options, allowing couples and planners to design a layout that suits their vision. Full-service event coordination is available, including vendor recommendations, custom wine pairings, and use of the Members’ Lounge for bridal parties or VIP guests. Guests are treated to exclusive wines and first-class hospitality throughout the event. Photography opportunities are endless, from vineyard rows to the sunset-lit patio. Whether it’s a rustic fall wedding or a summer evening soiree, Greenhill is a destination that brings elegance and authenticity to every celebration. On-site staff work closely with clients to ensure each event runs smoothly and beautifully. Event dates fill quickly due to the venue’s popularity, so early booking is essential.