Located in North Garden, south of Charlottesville on Route 29, Pippin Hill is one of Virginia’s most scenic vineyards. Lynn Easton and Dean Andrews, both with hospitality backgrounds, opened Pippin Hill to the public in 2011 with a focus on sustainable agriculture. Their website calls Pippin Hill “a culinary vineyard in the heart of Virginia’s wine country,” and this is one place where its definitely worth making a meal of it. The winemaker is state-wide star Michael Shaps. There is a sister property in Charleston, North Carolina, Cannon Green, for which one of the red wines here is named.
Wine. One of the Top 100 wineries in Virginia. Pippin Hill received six silver medals at the 2025 annual Virginia Governor’s Cup state-wide competition, for their 2019 Bundoran Blue (a red blend), and Wild Acre (a Tannat and Cab Franc blend), their 2021 Petit Verdot and Ridge Reserve, and 2023 vintage Viognier and Sauvignon Blanc. Their Petit Verdot and Chardonnay Reserve were awarded gold medals at the 2024 Governor’s Cup, while Pippin Hill wines were awarded a very impressive six gold medals back at the 2023 Virginia Governor’s Cup. The Pippin Hill 2017 Petit Verdot was voted one of the 12 best wines in Virginia (the “Governor’s Case”) at the 2020 Governor’s Cup competition. Pippin Hill’s multiple awards reflect the success which winemaker Michael Shaps has had in practically all his projects. The grapes are partly sourced from other vineyards in the area.
Setting. Three stars. Named as one of Virginia’s 10 most Beautiful Wineries, with inspiring views of the Blue Ridge Mountains and an architecturally handsome winery. In Summer wine tastings take place on an outdoor stone terrace. The associated Granary is a spectacular event space. Light fare offered for purchase, though the lunch and late-afternoon menu steals the show. Even better – book the Vintners Table and have a meal with courses paired with wines (for between 6 and 16 people).
Stories. Pairing Wine and Food. One of the great topics of wine professionals and amateurs alike is the pairing of wine and food. For the most part, wineries leave it to buyers and consumers to do it their way, but a handful of Virginia wineries are beginning to take advantage of the combination to attract even more visitors. Pippin’s four-course Vintner’s Table and Reserve Vintner’s Table (offered to groups of between 6 and 16 by reservation), are billed as an “exclusive ecotourism experience.” A sample menu includes Gazpacho paired with Viognier, a braised stablefish with mushrooms and clams paired with their Merlot, and a chocolate ganache tart paired with the Pippin Hill Meritage. As “events” such as weddings continue to be an important complementary source of revenue for many wineries in the state, one can imagine more wineries following the lead of Pippin Hill to make this kind of wine and food combination available beyond larger-scale events. The scenery doesn’t hurt.