The Hudson Valley’s craft beverage scene has matured into something resembling an ecosystem—orchards feeding cideries, grain fields feeding distilleries, and a dense network of breweries, wineries, and hybrid producers translating agriculture into drink. Festival season is where that ecosystem becomes visible. From early May through September, weekends fill with tastings that range from hyperlocal gatherings in orchard yards to sprawling fairground blowouts. Some lean educational, others purely hedonistic; many split the difference. What unites them is access: the chance to sample widely, meet makers, and get a sense of the region’s range in a single afternoon. The following roundup tracks the season, one pour at a time.
Angry Orchard Cider Tasting Festival
May 2 at Angry Orchard Cider House
Angry Orchard opens its Walden cidery to a broader slice of the region’s cider scene with this annual tasting festival, part of the larger Cider Week New York. The format is familiar but effective: multiple producers pouring side by side, offering a comparative look at styles ranging from crisp, fruit-forward pours to more tannic, farmhouse expressions. Expect live music, lawn games, and food from the kitchen, with VIP tickets offering early access and added perks. Set on the company’s 60-acre orchard, it’s both a showcase and a reminder of cider’s deep agricultural roots here. 12-5pm.
Catskills Cider Fest
May 9 at Seminary Hill Orchard and Cidery
Set on a hillside overlooking the Delaware River in Callicoon, Seminary Hill’s Catskills Cider Fest returns for its second year with a focused snapshot of New York’s booming cider scene. The gathering brings multiple producers into one place—last year’s lineup ranged from Brooklyn Cider House to Nine Pin—highlighting the range of styles emerging across the state. The host cidery adds its own draw: a striking Passive House facility and orchard rooted in multigenerational Callicoon farming. Beyond tastings, the day includes live music, outdoor food service, and optional prix-fixe dinners with cider pairings. 1-5pm, dinner seatings at 5:30pm and 7:30pm.
19th Annual Rip Van Winkle Wine, Brew & Beverage Festival
May 9 at Historic Catskill Point
Set along the Hudson River in Catskill, this long-running festival gathers wineries, breweries, and distillers for an afternoon of unlimited tastings in a postcard setting. Beyond the pours, the event leans into its community roots: local food vendors, craft goods, and live music create a relaxed, small-town fair atmosphere with a strong regional identity. Organized by the Fortnightly Club of Catskill, proceeds support local parks and recreation projects, giving the day a civic backbone. Rain or shine, it’s a reliable early season kickoff for the Hudson Valley’s craft beverage calendar. 11am-5pm.
TAP New YorkCraft Brew Festival
May 15-17 at Blackthorne Resort
The granddaddy of them all, TAP New York has been drawing serious beer pilgrims since 1998, evolving into one of the largest and longest-running craft brew festivals in the country. Now set at Blackthorne Resort in East Durham, the three-day blowout features 50-plus breweries pouring more than 150 beers, alongside cider, mead, and experimental hybrids. Each day has its own personality—Friday’s pairing dinner, Saturday’s Bacon, Brews & BBQ, and Sunday’s Brunch & Brews—plus live music, games, and late-night afterparties that stretch the weekend into a full-on Catskills retreat. Friday 5-7pm, Saturday 2-7pm, Sunday 11am-4pm.
Hudson-Berkshire Wine & Food Festival
May 23-24 on the Hudson-Berkshire Beverage Trail
The Hudson-Berkshire Wine & Food Festival unfolds across the Hudson-Berkshire Beverage Trail, linking a cluster of family-run producers for a Memorial Day weekend tasting tour through Columbia County and into the Berkshires. Participating stops include Hudson-Chatham Winery, The Vineyard at Windham, Whitecliff Vineyard & Winery, Olde York Farm Distillery & Cooperage, and Harvest Spirits Farm Distillery, each pouring handcrafted wines, spirits, and ciders alongside local food vendors. More than a single-site festival, it’s a roving invitation to explore the region’s beverage landscape at its source. Saturday 11am-6pm; Sunday 11am-5pm.
Ciders, Seltzers & Spirits Festival
May 24 at Barton Orchards
Barton Orchards in Poughquag leans into the lighter side of craft beverages with a festival devoted to cider, hard seltzer, and spirits—an increasingly prominent lane in the region’s drinkscape. Producers from across the Hudson Valley and beyond pour samples, offering a snapshot of where orchard fruit and distillation meet experimentation. The setting does some of the work: rolling farmland, food trucks, and live music create a casual, roam-and-sip rhythm. It’s less about beer maximalism, more about bright flavors and warm-weather drinking. A solid kickoff to summer’s outdoor festival season. 12-5pm.
Kest Fest
May 30 at Kestrel Tavern
Kestrel Tavern turns its Kingston yard into a showcase for the Hudson Valley’s deep bench of brewers, gathering an all-star local lineup for an afternoon tasting with a purpose. The roster spans stalwarts and newer names—Keegan Ales, Upward Brewing Company, Arrowood Farms Brewery, Kingston Standard, Industrial Arts Brewing Company, Catskill Brewery, Union Street, Wayward Lane, Great Life, West Kill Brewing, Mountain King, Slow Fox Farm Brewery, and Plan Bee Farm Brewery—offering a concise tour of the region’s beer landscape. Tickets are intentionally low-cost, with proceeds benefiting Miles of Hope, a Hudson Valley breast cancer charity, giving the day a philanthropic edge. 1-6pm.
Lasting Joy Brewery Fourth Anniversary
May 30 at Lasting Joy Brewery
Lasting Joy marks four years in Tivoli with an anniversary party that doubles as a snapshot of its evolving identity. The day centers on an exclusive anniversary brew release—details under wraps, but expect something that reflects the brewery’s playful, small-batch ethos—alongside a full slate of live music. The Kitchen + Taproom anchors the celebration with its usual rotation of thoughtful, seasonal fare, making this as much a food event as a beer one. It’s a chance to take stock of a brewery that has steadily built a loyal following without chasing trends. 12pm.
Silver Brothers Distillery Open House
June 6 at Silver Brothers Distillery
A new grain-to-glass operation comes online in Old Chatham as Silver Brothers opens its doors for tours and tastings, offering a first look at a distillery rooted in Hudson Valley agriculture. Set on a 220-acre historic farm, the project focuses on terroir-driven whiskey made from estate-grown grain and regional sources, with all spirits distilled, barreled, and aged onsite. Guests can walk the production spaces, visit the tasting room, and be among the first to try the debut 3-year Empire Rye. It’s both a launch and a statement of intent. 12pm.
Hudson Valley Fermentation Festival
June 13 at Twin Star Orchards
At Twin Star Orchards in New Paltz, fermentation gets its full-spectrum due: cider, wine, pickles, cheese, chocolate, and other microbially transformed pleasures gathered under one tent. The day unfolds as a tasting market with ticketed sessions for sampling, plus workshops, demos, and talks for those inclined to go deeper on the science and craft. This year’s keynote speaker, fermentation expert and author Kirsten Shockey, anchors the educational side with insights drawn from decades of hands-on practice. Live music runs throughout, while the orchard’s kitchen turns out wood-fired pizza, burgers, and barbecue. It’s equal parts county fair and culture lab. 11am-6pm.
Benmarl Sangria Festival (July & August Weekends)
Select Weekends in July and August at Benmarl Winery
Benmarl Winery stretches summer into two sangria-soaked weekends—one in July, one in August—turning its Marlboro hillside into a fruit-forward counterpoint to the region’s beer-heavy festivals. The draw is simple and effective: a lineup of house-made sangrias (think peach, berry, tropical, and citrus riffs) poured alongside sweeping Hudson River views. Tickets typically include a souvenir glass and multiple tastings, while the winery’s kitchen keeps pace with brick-oven pizza, barbecue, and casual fare. It’s less about deep dives, more about easygoing abundance—sun, sweetness, and a steady rotation of glasses. Runs 11am–8pm each day.
Tanabata Summer Festival
July 19 at Dassai Blue Sake Brewery
Dassai Blue brings a Japanese midsummer tradition to Hyde Park with its Tanabata Festival, a celebration rooted in the legend of star-crossed lovers Orihime and Hikoboshi, who are allowed to reunite just once a year across the Milky Way. Guests can expect a blend of cultural ritual and Hudson Valley terroir: writing wishes on colorful tanzaku paper to hang on bamboo, alongside sake tastings, seasonal food, and festival atmosphere. In Japan, Tanabata is as much about aspiration as celebration—a night of sending hopes skyward—recast here through the lens of a world-class sake operation. 11am-6pm.
Shawangunk Wine Trail Summer Sip
July 19, City Winery Hudson Valley
The Shawangunk Wine Trail distills its 13-member roster into a single afternoon at City Winery Hudson Valley in Montgomery, trading the usual winding backroad itinerary for a one-stop tasting of the region’s historic wine corridor. Founded in 1984, the trail spans some of the oldest vineyards in the country, with producers like Brotherhood Winery, Benmarl Winery, Whitecliff Vineyard & Winery, Robibero Winery, and Warwick Valley Winery & Distillery all pouring side by side. The setting—a striking adaptive reuse space set amid rolling vineyard views—anchors an easygoing day of live music, food, and lawn games. It’s the rare chance to taste the Gunks in one place. 11am-5pm.
Annual Seafood & Wine Festival
August 15-16, Robibero Winery
Robibero Winery in New Paltz pairs its Shawangunk Ridge views with a weekend built around a classic combination: seafood and estate wine. Hosted with Hooked Events, the festival features multiple stations serving everything from lobster rolls to oysters and grilled shrimp, designed to match the winery’s lineup of whites, roses, and light reds. Live music, lawn games, and vendor tents round out the scene, giving it the feel of a summer cookout scaled to vineyard size. VIP tickets add seated pairing experiences in the barrel room for those who want a more curated pass through the menu. 12-6pm.
Hudson Valley Wine & Food Festival
September 12-13 at the Dutchess County Fairgrounds
The Hudson Valley Wine & Food Festival is the big-tent version of the region’s craft beverage scene—a two-day sprawl in Rhinebeck that pulls together hundreds of wineries, breweries, distilleries, and specialty food producers in one place. Now more than two decades deep, it’s less a festival than a full-scale tasting ecosystem: chef demos, wine seminars, cocktail workshops, live music, and a dense marketplace of artisanal goods orbiting the central act of sampling. The sheer volume is the point—a snapshot of the Hudson Valley’s abundance, scaled up to fairgrounds size. Saturday 11am-6pm; Sunday 11am-5pm.
This article appears in May 2026.
