What's Happening in Orange, Ulster & Sullivan Counties NY This Weekend? June 5-7, 2026
By Brian Caplicki · Caplicki Home Team · Updated June 1, 2026 · 7 min read
Tacos on the Newburgh waterfront, 200 tractors rolling through Callicoon, a 27-year-old riverfront festival in Cornwall, the Pollinator Festival in Warwick, drive-in movies, brewery shows, and one of the biggest Touch-A-Truck days of the year. Here is your full Hudson Valley weekend guide for June 5-7, 2026.
The Hudson Valley summer calendar opens hard this weekend. Friday night brings live music across the wineries and breweries plus opening-month flicks at the Warwick Drive-In. Saturday belongs to Newburgh and Warwick. Sunday is the heaviest day of the three, with major free events stacked across Orange, Ulster, and Sullivan Counties. Here is what is worth your time, by day.
What is happening Friday, June 5 in Orange County NY?
Friday is the warm-up. The biggest day-of options are food, drink, and music at the breweries, wineries, and cideries that line the Black Dirt and Warwick Valley regions, plus a perfect weather forecast for the drive-in.
Warwick Drive-In Theater (5 Warwick Tpke, Warwick) is open all weekend with three screens showing the latest blockbusters under the stars. Open since 1950, it is one of the last great drive-ins in the region. Bring lawn chairs and a blanket. Gates typically open around 7:30 PM with movies starting at dusk.
Newburgh Brewing Company on the riverfront hosts live music Friday and Saturday nights. The taproom, food, and Hudson River views are reason enough on their own. The Drowned Lands in Warwick (a perennial Best New Brewery winner), Pennings Farm Cidery in Warwick, and Equilibrium Brewery in downtown Middletown all run weekend programming. Equilibrium is open Friday 12-10 PM with a beer garden and BBQ program. Check each venue's website for Friday's lineup.
Up in Sullivan County, Roscoe Beer Company (Roscoe) is open Friday 12-9 PM in "Trout Town USA," Catskill Brewery in Livingston Manor is open with their food truck, and Upward Brewing Company in Livingston Manor sits on a 120-acre nature preserve with sunset views you won't forget. There is also a First Friday Networking Breakfast at the Forestburgh Playhouse from 7:30-9:00 AM hosted by the Sullivan County Chamber, perfect for early risers who want to meet local business owners.
Ulster County's drink scene is open too. Tuthilltown Spirits Distillery in Gardiner (NY's first distillery since prohibition, home of Hudson Whiskey) runs Friday 12-8 PM with tours by appointment ($30 includes a 6-sample tasting and souvenir glass). Whitecliff Vineyard in Gardiner and Arrowood Farms in Accord (a terroir-driven farm brewery and distillery with a new on-site restaurant) are both open for the weekend.
What is happening Saturday, June 6 in Orange County NY?
Hudson Valley Taco Fest 9 takes over People's Waterfront Park in Newburgh from 1:00 PM to 5:30 PM. Now in its ninth year, it is the largest taco festival in the region, with 44 taco varieties, burritos, churros, street corn, vegan and gluten-free options, live Latin music, and Hudson River sunset views. The lineup this year includes Gerardo Ortiz, Los Inquietos Del Norte, Los Pescadores Del Rio Conchos, and Los Del Convoy. This is a 21+ festival with three ticket tiers (General Admission, Party Pass, VIP). Kids 12 and under are free. The event sold out last year, so do not show up at the gate without tickets.
Hudson Valley Pollinator Festival (Day 1) runs Saturday June 6 from 12:00 PM to 5:00 PM at Warwick Valley Winery & Distillery in Warwick. Now in its fourth year and presented in partnership with Orange Environment, the festival features live music, a British car show, artisan vendors, environmental exhibits, a native plant sale, and free milkweed plants while supplies last. Admission is $5. 100% of proceeds support the Hudson Valley Pollinator Project. The wine is good. The cause is better. Bring the family and stay for the music.
Pennings Farm Cidery Honor Flight Festival in Warwick runs Saturday June 6 from 12:00 PM to 8:00 PM with a stacked live music lineup: Fiddle Frenzy, Bunker Boys, West Milford Bagpipers, and Soulshine Band. Cider, food, and family-friendly farm fun for an excellent cause. Pennings is one of Orange County's premier cidery destinations and the music day is one of the best of their season.
Catskill Brewery in Livingston Manor (Sullivan County) hosts That 70's Project live at 2:00 PM Saturday June 6. Pair it with the Catskill Food Truck on-site for a perfect afternoon in the heart of the Western Catskills.
Heart of the Hudson Valley Farmers' Market in Milton (Ulster County) celebrates opening day Saturday June 6 from 9:00 AM to 2:00 PM at Cluett-Schantz Memorial Park, 1801-1805 Route 9W. Local produce, baked goods, artisan products, and the first taste of summer's best vendors.
What free family events are happening Sunday, June 7?
Sunday is the heart of the weekend. Three free, family-friendly events run at the same time across three counties, so plan your route.
Cornwall-on-Hudson RiverFest (Orange County) celebrates its 27th year at Donahue Memorial Park, right on the Hudson River. Hours are 11:00 AM to 6:00 PM. Expect live music across multiple stages, food vendors, craft and artisan booths, kids' activities, and one of the prettiest riverfront settings in the Hudson Valley. Admission is free.
New Paltz Rotary Touch-A-Truck (Ulster County) runs 9:00 AM to 3:00 PM at the Ulster County Fairgrounds, 249 Libertyville Road. Kids can climb on and explore fire trucks, dump trucks, excavators, tow trucks, and emergency vehicles. The first hour (9-10 AM) is a designated sensory-friendly quiet hour, which is a thoughtful touch for kids who need a calmer entry point. Bounce houses, face painting, and food are on site. Proceeds support Rotary charitable programs for local families.
Callicoon Tractor Parade (Sullivan County) is a 30-year tradition. More than 200 tractors, from vintage Farmalls to modern Kubotas, roll down Lower Main Street in Callicoon starting at noon. The parade runs until 3:00 PM and ends with a community BBQ at the Delaware Youth Center. Free to attend, free to enter your own tractor (registration opens at 7 AM at the DYC). It is one of the most photographed events in Sullivan County every year.
What else is worth doing this weekend?
Hudson Valley Pollinator Festival (Day 2) at Warwick Valley Winery runs again Sunday June 7 from 12:00 PM to 5:00 PM. If you missed Saturday, this is your second chance, and Sunday tends to be the slightly mellower of the two days. Same $5 admission.
Warwick Valley Farmers' Market is open Sunday June 7 from 9:00 AM to 2:00 PM at the South Street parking lot in the Village of Warwick. It is the largest farmers market in Orange County by vendor count, drawing more than 40 producers on a typical summer Sunday: farm-fresh produce, pastured meats, baked goods, flowers, honey, maple syrup, and craft beverages. Live music most weeks. Bring a tote. Pair it with the Pollinator Festival a few miles down the road for a perfect Warwick Sunday.
Scout Day at LEGOLAND New York in Goshen kicks off Sunday June 7 at 10:00 AM. A natural pairing for families with scouts, or for any kids who would rather chase a roller coaster than a tractor.
Pennings Farm Cidery closes out the weekend with Jeff Wernts in the Beer Garden Sunday June 7 from 3:00-6:00 PM. The cidery's beer garden is one of the prettiest Sunday-afternoon spots in Orange County.
The Hudson Valley wine and beer trail this weekend
If you would rather skip the crowds and make your own weekend, the Hudson Valley wine, beer, cider, and spirits scene is in peak early-summer form. Here are the standout local venues open across all three counties from Friday through Sunday.
Orange County
Warwick Valley Winery & Distillery hosts the Pollinator Festival both days (above) plus their regular tasting room. Brotherhood Winery in Washingtonville is America's oldest winery (1839) and runs daily tours and tastings. Pennings Farm Cidery in Warwick has live music both Saturday and Sunday (above). The Drowned Lands Brewery in Warwick is widely considered one of the best breweries in New York State, with an industrial taproom, pizza, and weekend live music. Newburgh Brewing Company on the Newburgh waterfront has Friday and Saturday night music. Equilibrium Brewery in downtown Middletown features a taproom, beer garden, BBQ program, and retail (Fri 12-10, Sat 11-10, Sun 11-7).
Ulster County
Tuthilltown Spirits Distillery in Gardiner is NY's first distillery since prohibition and the home of Hudson Whiskey. Tours run by appointment (45 minutes, $30, includes a 6-sample tasting and souvenir glass). Open Fri 12-8, Sat 12-8, Sun 12-6. Whitecliff Vineyard & Winery at the base of the Shawangunk Mountains in Gardiner is one of the prettiest tasting rooms in the region (Thu-Sun 12-5:30). Robibero Family Vineyards in New Paltz is a 42-acre dog-friendly winery with wood-fired pizza on weekends. Adair Vineyards in New Paltz pours in a 220-year-old barn. Stoutridge Vineyard in Marlboro runs on 100% solar with underground cellars built into the hillside. Magnanini Winery in Wallkill is famous for Sunday family-style Italian dinners. Arrowood Farms in Accord is a terroir-driven farm brewery and distillery with a new on-site restaurant and rotating kitchen pop-ups. Keegan Ales in Kingston (founded 2003) anchors the Kingston brewery scene with live music in the taproom.
Sullivan County
Catskill Brewery in Livingston Manor has live music (That 70's Project) Saturday at 2 PM plus a rotating food truck. Upward Brewing Company in Livingston Manor sits on a 120-acre nature preserve with one of the most photographed views in the Catskills. Roscoe Beer Company in Roscoe (Trout Town USA) is one of the original Sullivan County craft breweries (Fri 12-9, Sat 11-9, Sun 11-6). Two Farms Brewing in Bloomingburg is on a long dirt road framed by lavender fields and rows of hops, a quiet hidden gem worth the drive. Catskill Distilling Company in Bethel is open weekends and by appointment for tours and tastings of small-batch spirits.
The weekend at a glance
June 5-7, 2026 events
| Event | Day & Time | Location | County |
|---|---|---|---|
| Warwick Drive-In (3 screens) | Fri-Sun, dusk | 5 Warwick Tpke, Warwick | Orange |
| Newburgh Brewing live music | Fri & Sat evenings | 88 South Colden St, Newburgh | Orange |
| Hudson Valley Taco Fest 9 (21+) | Sat 1:00-5:30 PM | People's Waterfront Park, Newburgh | Orange |
| Pennings Honor Flight Festival (4 bands) | Sat 12:00-8:00 PM | Pennings Farm Cidery, Warwick | Orange |
| Catskill Brewery: That 70's Project live | Sat 2:00 PM | Catskill Brewery, Livingston Manor | Sullivan |
| Hudson Valley Pollinator Festival | Sat & Sun 12-5 PM ($5) | Warwick Valley Winery | Orange |
| Heart of the HV Farmers' Market (opening day) | Sat 9:00 AM-2:00 PM | Cluett-Schantz Park, Milton | Ulster |
| Cornwall-on-Hudson RiverFest | Sun 11:00 AM-6:00 PM | Donahue Memorial Park | Orange |
| New Paltz Rotary Touch-A-Truck | Sun 9:00 AM-3:00 PM | Ulster County Fairgrounds, New Paltz | Ulster |
| Callicoon Tractor Parade (30th annual) | Sun 12:00-3:00 PM | Lower Main St, Callicoon | Sullivan |
| Warwick Valley Farmers' Market | Sun 9:00 AM-2:00 PM | South St Lot, Warwick | Orange |
| Scout Day at LEGOLAND NY | Sun 10:00 AM+ | LEGOLAND, Goshen | Orange |
| Pennings: Jeff Wernts in the Beer Garden | Sun 3:00-6:00 PM | Pennings Farm Cidery, Warwick | Orange |
Sources: river-fest.com, eventbrite.com (Hudson Valley Taco Fest 9), Delaware Youth Center, Rotary District 7210, Warwick Valley Farmers' Market. Always confirm hours with the host before traveling.
Why Hudson Valley sellers should pay attention
The first three weekends of June are some of the highest-traffic open-house weekends of the entire year in Orange County NY. Buyers who waited out the spring are looking to lock something in before the late-summer slow-down. If your home is sitting on the market, this is the window where price corrections and refreshed photography pay off the fastest. If you are still thinking about listing, the calendar is on your side. We can talk strategy and pull a current valuation in one short call.
Why Hudson Valley buyers should pay attention
Weekends like this one are the best free tour of the Hudson Valley you will ever get. If you are house-hunting in Orange, Ulster, or Sullivan County, use this weekend to actually live the neighborhoods. Walk Cornwall's waterfront. Hit the Warwick farmers market. Drive the back roads from Callicoon. The towns that feel right on a Sunday in June are the towns you will want to live in year-round. When you find one, we know what is coming on the market before it hits Zillow.
The bottom line
June 5-7, 2026 is a stacked Hudson Valley weekend. Newburgh on Saturday, then Cornwall, New Paltz, Callicoon, Warwick, and Goshen all on Sunday. If you are deciding between Orange, Ulster, and Sullivan County for your next home, this is the weekend to see what each one feels like. Park the GPS. Talk to vendors. Watch which town pulls at you. That is the one to call us about Monday.
Curious what your home is worth in today's Hudson Valley market?
Get a free, instant, data-driven estimate of your Orange County, Ulster County, or Sullivan County home's current value. No phone call required, no obligation. Or, if you are buying, reply and tell us what you saw this weekend that made you think.
Hudson Valley Weekend Events FAQ
What is happening in Orange County NY this weekend, June 5-7, 2026?
Friday June 5 has live music at Newburgh Brewing Company, The Drowned Lands in Warwick, and Pennings Farm Cidery, plus opening-weekend movies at the Warwick Drive-In. Saturday June 6 brings Hudson Valley Taco Fest 9 to People's Waterfront Park in Newburgh (1-5:30 PM, 21+) and Day 1 of the Hudson Valley Pollinator Festival at Warwick Valley Winery (12-5 PM). Sunday June 7 stacks Cornwall-on-Hudson RiverFest at Donahue Memorial Park (11 AM-6 PM), the Warwick Valley Farmers' Market (9 AM-2 PM), Scout Day at LEGOLAND New York in Goshen, and Day 2 of the Pollinator Festival.
What is the Hudson Valley Pollinator Festival?
The 4th Annual Hudson Valley Pollinator Festival runs Saturday and Sunday, June 6-7, 2026 from 12-5 PM at Warwick Valley Winery & Distillery in Warwick, NY. Admission is $5. The festival features live music, a British car show, artisan vendors, educational exhibits, a native plant sale, free milkweed plants while supplies last, and 100% of proceeds benefit the Hudson Valley Pollinator Project.
Are there free family events in the Hudson Valley this weekend?
Yes. Cornwall-on-Hudson RiverFest is free to attend on Sunday June 7 from 11 AM to 6 PM at Donahue Memorial Park. The Callicoon Tractor Parade in Sullivan County is also free and rolls down Lower Main Street starting at noon with more than 200 tractors. The Warwick Valley Farmers' Market is free to browse and runs every Sunday.
What is Hudson Valley Taco Fest 9 and where is it?
Hudson Valley Taco Fest 9 is the area's largest taco festival. It runs Saturday June 6, 2026 from 1 PM to 5:30 PM at People's Waterfront Park in Newburgh. Expect 44+ taco varieties, live Latin music, vendors, and Hudson River views. It is a 21+ event with separate VIP, Party Pass, and General Admission tickets. Kids 12 and under are free.
What is the Callicoon Tractor Parade?
The Callicoon Tractor Parade is a 30-year-old Sullivan County tradition that draws more than 200 vintage and modern tractors down Lower Main Street in Callicoon on the second Sunday of June. The 2026 parade runs from noon to 3 PM on Sunday June 7, followed by a community BBQ at the Delaware Youth Center. Admission and parade entry are free.
What is the best Sunday family event in Ulster County NY on June 7, 2026?
The New Paltz Rotary Club Touch-A-Truck at the Ulster County Fairgrounds, 249 Libertyville Road, runs Sunday June 7 from 9 AM to 3 PM. Kids can climb on fire trucks, dump trucks, excavators, and emergency vehicles. The 9-10 AM hour is a designated sensory-friendly quiet hour. Bounce houses and face painting are included. Proceeds support Rotary charitable giving.
What are the best Hudson Valley wineries and breweries to visit this weekend?
In Orange County, head to Warwick Valley Winery (Pollinator Festival both days), Pennings Farm Cidery (live music Saturday and Sunday), Brotherhood Winery in Washingtonville (America's oldest, 1839), The Drowned Lands Brewery in Warwick, and Equilibrium Brewery in Middletown. In Ulster County, Tuthilltown Spirits in Gardiner offers Hudson Whiskey tours, plus Whitecliff Vineyard, Robibero Family Vineyards, Stoutridge Vineyard, Arrowood Farms in Accord, and Keegan Ales in Kingston. In Sullivan County, Catskill Brewery in Livingston Manor has live music Saturday, plus Upward Brewing on a 120-acre nature preserve, Roscoe Beer Company in Trout Town USA, and Catskill Distilling in Bethel.
Where can I see live music in Orange County NY this weekend?
Pennings Farm Cidery in Warwick has the deepest live music lineup: an all-day Honor Flight Festival Saturday June 6 from 12-8 PM with four bands (Fiddle Frenzy, Bunker Boys, West Milford Bagpipers, Soulshine Band), and Jeff Wernts in the Beer Garden Sunday June 7 from 3-6 PM. Newburgh Brewing Company runs Friday and Saturday night music on the waterfront. The Hudson Valley Pollinator Festival at Warwick Valley Winery has live music all day Saturday and Sunday 12-5 PM. Hudson Valley Taco Fest 9 in Newburgh Saturday afternoon features a Latin music lineup including Gerardo Ortiz.
Is Orange County NY a good place to live for families who love local events?
Yes. Orange County NY hosts a deep calendar of weekly farmers markets, riverfront festivals, museum days, and parades from May through October, with easy access to neighboring Sullivan and Ulster County events. Towns like Warwick, Cornwall, Goshen, and Newburgh anchor the social calendar. The Caplicki Home Team works with buyers across every Orange County NY zip code and can match you to the neighborhoods that fit your family's pace.
Are open houses still active in Orange County NY in early June?
Yes. Early June is one of the strongest open-house weekends of the year in Orange County NY. The weather is reliable, schools are still in session, and serious buyers are looking to lock in a home before late-summer moves. If you are thinking about listing, the next three weekends are some of the highest-traffic windows of 2026.
How is the Hudson Valley real estate market right now?
The Hudson Valley remains a tight, in-demand market in June 2026, with Orange County NY inventory still below pre-pandemic levels. Well-priced homes in Warwick, Cornwall, Goshen, New Paltz, and the Sullivan Catskills continue to attract multiple offers. The Caplicki Home Team can pull a free, data-driven valuation on your home in under 30 seconds at caplickihometeam.com.
The Caplicki Home Team is a Keller Williams HVU real estate team based in Middletown, NY, serving Orange County, Sullivan County, Ulster County, and the broader Hudson Valley. Reach us at 845-656-4498 or hello@caplickihometeam.com.
