On 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.
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
Harpersfield VineyardSince 1979, family-owned Harpersfield Vineyard has grown grapes and made estate-bottled wines on its working farm in Ohio’s Grand River Valley. Its Geneva tasting room pairs those hand-picked-fruit wines with seasonal kitchen fare, vineyard views, live weekend music, and a fireside setting in colder months.GENEVA, OH
Stever Hill VineyardsStever Hill Vineyards is a fifth-generation family farm and winery on the hills above Keuka Lake, producing about 2,000 cases of Finger Lakes wine each year. The Tones family’s grape-growing story began in 1951, and today brothers Harold, Don, and Jim oversee the operation with vineyard managers Jon and Mike Tones and winery managers Liz and Jay Sprague. Visitors can taste the estate’s dry, semi-dry, and sweet wines in the renovated 1850s Crooked Barn Tasting Room, surrounded by hundreds of acres of grapes.BRANCHPORT, NY
Buttonwood Grove WinerySince David and Melissa Pittard purchased the property in 2014, Buttonwood Grove Winery has grown into a family-run Finger Lakes winery producing estate wines beside Cayuga Lake. Dave’s roots at the fourth-generation Beak & Skiff Apple Farm inform the Pittards’ blend of agriculture and winemaking, while the family’s expansion of the vineyards and new winemaking building carries the property into its next chapter. Its 2016 Riesling won the 2017 Governor’s Cup as New York State’s best wine, and the site now pairs tastings with lakeside music and cabins among the vines.ROMULUS, NY