Fall drinking in the Hudson Valley is rarely a sit-still affair. One weekend might find you hurling a keg in Warwick or stomping grapes in New Paltz; the next, pairing pumpkin ravioli with Riesling in Montgomery or raising a stein beneath Catskills foliage. From October through December, the region’s breweries, wineries, cideries, restaurants, and farms turn harvest season into a celebration of what is grown, fermented, cooked, and poured here.
This year’s calendar balances excess—lederhosen, tribute bands, haunted houses, purple feet—with more polished pleasures, including multicourse wine dinners, a Thanksgiving-inspired vineyard feast, and a holiday tasting trail. Many gatherings add live music, makers, family activities, and dramatic scenery to the drinks themselves. Whether your fall ritual involves festbier, hard cider, estate wine, caramel-apple sangria, or an unusually athletic barrel, these events offer plenty of reasons to leave the house, fill a glass, and toast the season with neighbors.
Catskill Food Festival
October 3, Catskill
The Catskill Food Festival returns to Dutchman’s Landing Park on October 3, bringing a waterfront spread of food trucks and local vendors to the village. From noon to 6pm, visitors can graze their way through the afternoon while listening to live music and browsing artisan and specialty booths. New this year, the rain-or-shine festival has expanded its roster of non-food vendors. Families can also take advantage of the park’s newly upgraded, accessible playground for children.
Hudson Oktoberfest
October 3, Upper Depot Brewing Co.
Hudson’s biggest Oktoberfest yet takes over Upper Depot Brewing inside the city’s historic train station. More than 15 regional craft beers, wines, and ciders join food vendors, local makers, games, contests, and family-friendly activities. Four bands keep the party moving: Jungle Love, the Dylan Doyle Band, Athron, and headliner Mo Lowda & the Humble. Well-behaved dogs are welcome, and five dollars from each full-price ticket supports participating animal shelters and rescue organizations across the region.
Robibero Winery Grape Stomping Festival
September 26-27 and October 3-4, New Paltz
Robibero turns grape stomping into an all-day vineyard field day, where stained soles are only the beginning. Between trips to the stomping bins, festivalgoers can settle in with Robibero wines, wood-fired pizza, meats and cheeses, then rally for lawn games or warm up beside the bonfires. Live music keeps the party moving, and children under 12 can join the squishing free. Come prepared to sip, snack, play, and leave with memories and thoroughly incriminating feet.
City Winery Chef & Winemaker Dinner Series
October 4, October 25, November 20 in Montgomery
City Winery Hudson Valley’s Chef & Winemaker Dinner Series turns three seasonal themes into pairings by chef Matthew Stolz and winemaker Travis Van Caster. The Fall Harvest Table moves from delicata squash to cider-brined pork and apple tart; Sweet Notes explores savory-edged desserts including corn panna cotta and goat cheese cheesecake; and From Masa to Mole travels through esquites, shrimp aguachile, duck al pastor, mole poblano, and mango chamoy cheesecake—all matched with City Winery pours.
Drowned Lands Oktoberfest
October 10-11, Warwick
At Drowned Lands, Oktoberfest comes with a reminder that kegs are good for more than holding beer. The brewery’s beloved keg toss joins stein-holding competitions and live music for two days of Bavarian-style revelry in the Warwick Valley. Lagers and festbier flow alongside German food specials, fueling feats of questionable strength and enthusiastic cheering. Dust off the lederhosen, practice your lifting form, and prepare to discover whether your talents lie in drinking, holding, or hurling.
Benmarl Winery Grape Stomping Festival
October 10-11, Marlboro
There are dignified ways to appreciate wine. Grape stomping is not among them. Benmarl Winery’s harvest festival invites visitors to kick off their shoes, climb into a tub, and squish grapes between their toes—preferably while friends document the evidence. The weekend also offers tastings of six wines, beer, sangria, live music, hayrides, brick-oven pizza, and barbecue. All unfold against Benmarl’s sweeping Hudson Valley views, proving that wine culture can survive a little purple-footed foolishness.
Curses & Cocktails
October 8 & October 15, Angry Orchard in Walden
At Angry Orchard’s Cider House, cocktail hour takes a turn toward the supernatural during Curses & Cocktails, a hands-on mixology class. Guests learn to build Halloween-inspired drinks using the cidery’s hard cider while picking up techniques they can bring to their own autumn gatherings. The Walden orchard supplies an appropriately atmospheric setting for stirring up something darker than the usual cider pour. Equal parts workshop and spooky night out, the class is open to adults.
Hunter Mountain Oktoberfest
October 10-11, Hunter
Hunter Mountain’s three-weekend Colors in the Catskills celebration goes Bavarian October 10-11 with Oktoberfest, pairing peak-season scenery with beer, German-inspired food and live entertainment. Visitors can raise a stein at the mountain’s base, browse vendors and take in the surrounding foliage, with scenic chairlift rides offering a higher vantage point. Formerly a multiday Oktoberfest, the reconfigured fall festival devotes its middle weekend to the beloved combination of brats, brews and Catskills color.
Tilly Foster Farm Oktoberfest
October 11, Brewster
Tilly Foster Farm swaps polkas for power chords at this Oktoberfest concert starring BoStyx, a tribute band devoted to the arena-rock catalogs of Boston and Styx. Expect soaring harmonies, guitar heroics, cold beer, and a crowd primed to sing along from the opening riff through the encore. Food concessions and a fully stocked bar keep everyone fueled, while VIP admission adds an Oktoberfest buffet. Bring a chair or blanket for this rain-or-shine outdoor concert celebration.
Boos and Brews
October 17-18, Barton Orchards in Poughquag
Barton Orchards leans into spooky season with five pumpkin and Oktoberfest beers, an Oktoberfest-inspired menu, and live music at its Poughquag farm. Between rounds at the taps, visitors can pick apples and pumpkins, tackle the corn maze, tour the haunted house, and visit the petting zoo. Hayrides, a carousel, and the Fun Park keep younger revelers occupied, making this a Halloween celebration with attractions for cider-drinking grownups and costume-ready kids in tow all weekend.
New York Cider Festival
November 14 at Red Hook Cidery in Red Hook, Brooklyn
New York’s apple harvest heads to Brooklyn for the New York Cider Festival, hosted by the New York Cider Association at Red Hook Cidery. Cider makers from across the state will pour samples spanning the drink’s range, giving enthusiasts and the cider-curious a chance to compare styles, talk with producers, and bring home favorite bottles. Food pairings and shopping round out a gathering devoted to fermented fruit—and the growers, orchards, and craft behind every glass.
Milea Estate Harvest Gathering
November 14, Staatsburg
Thanksgiving gets an early dress rehearsal at Milea Estate Vineyard’s Harvest Gathering, a communal feast built around the bounty of the season. Guests will share a three-course, family-style meal of chef-crafted autumn dishes, accompanied by estate-grown wines and new releases from the cellar. Communal seating encourages conversation across the table, while exclusive holiday wine offers provide an excuse to stock up before entertaining season. Expect generous plates, polished pours, and Milea’s warm Hudson Valley hospitality.
Holiday Fineries at the Wineries
November 21-December 12, Shawangunk Wine Trail
Holiday Fineries at the Wineries turns the Shawangunk Wine Trail into a progressive seasonal tasting room. Visitors choose an itinerary through festively decorated wineries and cideries, sampling local wine and cider flights along the way. Based on previous editions, each stop also supplies a keepsake, with the completed route yielding a collection of holiday ornaments and a commemorative glass. The self-guided event doubles as a chance to stock the holiday table with Hudson Valley bottles.
