5 Places to Pick Apples and Drink Wine

Around this time every year, the photos of rosé and beach vacations that flooded Instagram throughout the summer are replaced with back-to-school montages and snaps of apple orchards. Honestly, is it even fall if you don’t visit a pumpkin patch and document every wool sweater-swathed moment? And while the annual farm visit is an essential part of autumn, do you know what’s even better? An apple orchard with a winery. (Or, in at least one case, a winery with an apple orchard.) Below, find five orchards where you can sip wine while soaking up fall.

Apple Barn Orchard & Winery, Elkhorn, WI

Less than a two-hour drive from Chicago, situated a little north of Lake Geneva, this quaint, family-run farm looks like something from a Norman Rockwell painting, with sweeping green fields and a classic red barn. Pick your own strawberries in the summer, and in the fall choose from more than a dozen varieties of apples. Some are used to make their award-winning Honey Crisp Apple Harvest wine—one of the non-grape fruit wines they produce (including strawberry, peach, and pear.) A little country store sells caramel apples, cider, and Wisconsin cheese (of course), plus homemade baked goods, and the last weekend in September, the Orchard will host its 30th annual Apple Fest, with hayrides, a pumpkin patch, apple treats (like the caramel apple delite, a chopped apple topped with caramel, nuts, and whipped cream), and plenty of wine samples.

Terhune Orchards, Princeton, NJ

There are plenty of pumpkin patches in the Tri-State area, but Terhune Orchards is one of New Jersey’s only farms with a winery and tasting room, making this the obvious choice for a fall outing. The 185-acre, family-run farm grows more than 40 crops, including cherries, carrots, kale, and rhubarb. About half of those acres are orchards, growing dozens of varieties of apples, and five acres are dedicated to the pumpkin patch. (The perfect place to survey the scene for a spectacular Jack-o-lantern.) Red and white wines are made using grapes grown in the vineyards on site, and fruit wine is made using the orchard’s apple cider. Sample them all in the tasting room located inside the 150-year-old red barn, and before you leave, stop into the farm store to browse the selection of homemade fruit pies and cider donuts, local honey, and fresh-pressed cider.

Warwick Valley Winery & Distillery, Warwick, NY

Through the months of September and October, this picturesque Hudson Valley winery and distillery opens for apple picking. Ride a tractor to the orchards and fill bags from among the 60 different types of apple trees, and afterward, stop into the rustic tasting room. Once an old apple packing house, the restored space is now a snug setting to sample from the robust lineup of wine, fruit brandy, and the award-winning Doc’s Cider, also made here. Find a seat on the patio and sip a Bourbon Barrel Aged Apple Liqueur, one of the apple brandies made here under the name American Fruits Distillery (the first fruit distillery in New York.) On weekends, live music complements the wine and views, and several times a year the winery hosts music festivals featuring classic tribute bands.

Russell Orchards and Winery, Ipswich, MA

On the North Shore of Massachusetts, a little over 30 miles from Boston, this 120-acre, family-run fruit farm is quintessentially New England. In the summer, families take a break from nearby Crane Beach to gather strawberries, raspberries, and cherries, and in fall, come to pick ten varieties of apples and visit with a barnyard full of animals, including chickens, pigs, rabbits, and donkeys. Inside the barn, an inviting little tasting room is centered around a massive stone fireplace, making for a cozy spot to sip housemade wine and cider. Don’t leave without a visit to the farm store, selling hot cider donuts, made-from-scratch using cider pressed in the mill on the grounds, from apples grown in the orchard.

Hilltop Orchards, Richmond, MA

In western Massachusetts, the historic Hilltop Orchards is one of the last remaining apple orchards in the Berkshires. The 200-acre property is home to 26 varieties of apple—including Honeycrisp, Ginger Gold, and some heirlooms that date back to when the orchard first began, over a century ago. Explore the grounds and fill a bag of apples while taking in the area’s legendary fall foliage from the eponymous hilltop perch. When it’s time to take a break, there are a few solid sipping options, including the cold-pressed cider, hard, French-style Cidre, and a lineup of award-winning wines, made here under the label Furnace Brook Winery. Pick up a few bottles to take home, along with a fresh-baked apple pie.