On the former estate of New Market co-founder Nicholas Hall Sr., New Market Plains Vineyard makes wine from a farm that has remained in the Hall family since the 1760s. Howard and Susan Wilson now operate the vineyard and winery, with Susan a direct Hall descendant and the property in its 11th generation of family stewardship. The vineyards were replanted in 2012, and the first vintage was harvested in 2014 in a restored 1941 tile dairy barn.
Dove Valley WineryOn a 100-acre family farm outside Rising Sun, Dove Valley Winery makes wines from its own vineyard, which Harry and Janet Hepbron planted in 1998 as Cecil County’s first vineyard and winery. The multi-generation operation was built as a family legacy, and its wines have earned Best in Class and medal recognition at the Maryland Governor’s Cup and Finger Lakes International competitions.RISING SUN, MD
Victory View VineyardOn a rural farm in North Easton, Mary and Gerry Barnhart grow cold-climate grapes and handcraft estate wines at their family-owned Victory View Vineyard. The retired public-service couple began planting test vines after deciding to keep their farm in agriculture, and today their children and grandchildren help with vineyard work, bottling, and harvest. Their mostly dry wines draw on the Upper Hudson region’s rural roots and local history, with every grape grown on the property.SCHAGHTICOKE, NY
Loughlin VineyardOn Sayville’s historic John Ellis Roosevelt Estate, Loughlin Vineyard grows grapes and makes wine on-site in a family vineyard founded by Barney and Christine Loughlin in 1984. The 10-acre farm has produced its own wine since 2006, while Barney’s daughters carried on the operation until his granddaughter Brittany took ownership in 2025. Its tasting room and laid-back events preserve the vineyard’s distinctly multigenerational South Shore character.SAYVILLE, NY
Red Heifer WineryOn a 56-acre Smithsburg hillside that was once the Naylor Peach Orchard, Kevin and Yvonne Ford run Red Heifer Winery, making wine from a vineyard planted in 2010. Owner and winemaker Kevin Ford processes, ages, and bottles every wine on-site, while the family farm’s history—from peaches and apples to dairy and hay—still shapes the winery’s character. Opened in November 2012, the adults-only winery pairs its dry and sweet wines with sweeping views of the surrounding mountains.SMITHSBURG, MD