What's Happening in Orange, Ulster & Sullivan Counties NY This Weekend? June 12-14, 2026
By Brian Caplicki · Caplicki Home Team · Updated June 8, 2026 · 8 min read
Strawberry fields and LEGOLAND for the kids, winery music and craft beer for the grown-ups, and festivals for everyone. Here is your June 12-14, 2026 Hudson Valley weekend, sorted three ways.
Quick Answer
The June 12-14, 2026 weekend is loaded across Orange, Ulster, and Sullivan Counties. For kids: LEGOLAND New York in Goshen, pick-your-own strawberries in Warwick and Newburgh, and the Hudson Highlands Nature Museum. For adults: winery and brewery live music all weekend, from Dylan Doyle at Warwick Valley Winery to an all-day Drowned Lands Summer Concert. For the whole family: the Backpack Snack Attack festival at Pennings Farm, the Hudson Valley Fermentation Festival at Twin Star, the Livingston Manor Trout Parade, and three farmers markets. June 14 is Flag Day, not Father's Day, so the calendar is wide open.
The Hudson Valley summer calendar is in full swing, and this weekend has something for every age. Rather than march through it day by day, here is the whole thing sorted by who you are bringing: the kids, the grown-ups, or everybody at once. Mix and match across the three counties to build your perfect Saturday and Sunday.
The weekend at a glance
June 12-14, 2026 events
| Event | Day & Time | Location | For |
|---|---|---|---|
| LEGOLAND New York | Sat-Sun 10 AM-5 PM | Goshen (Orange) | Kids |
| Pick-your-own strawberries | Daily 9 AM | Ochs (Warwick), Lawrence (Newburgh) | Kids |
| Hudson Highlands Nature Museum | Sat-Sun | Cornwall (Orange) | Kids |
| Dylan Doyle / Soul Sense (winery music) | Sat & Sun 2-5 PM | Warwick Valley Winery | Adults |
| Drowned Lands Summer Concert (3 acts) | Sat 12-7:30 PM | Drowned Lands, Warwick | Adults |
| Moonshine Creek (Fri) / Alyssa Goldstein (Sun) | Fri 6-9 / Sun 3-6 PM | Pennings Beer Garden, Warwick | Adults |
| Newburgh Brewing World Cup watch party | Fri evening | Newburgh (Orange) | Adults |
| Sugar Loaf PAC: Slippery When Wet (Bon Jovi tribute) | Fri | Sugar Loaf (Orange) | Adults |
| Bethel Woods: John Pizzarelli (Jazz at Lincoln Center) | Fri 8 PM | Bethel (Sullivan) | Adults |
| Bethel Woods: True Colors Tour (Cyndi Lauper, B-52s) | Sun | Bethel (Sullivan) | Adults |
| Backpack Snack Attack Music Festival (4 bands) | Sat 12-8 PM | Pennings Farm, Warwick | Family |
| Hudson Valley Fermentation Festival | Sat 11 AM-6 PM | Twin Star Orchards, New Paltz | Family |
| Livingston Manor Trout Parade (20th yr) | Sat 12 PM, Main St | Livingston Manor (Sullivan) | Family |
| St. Augustine's Bazaar & Food Truck Fest (free) | Fri-Sun | Highland (Ulster) | Family |
| Beacon Sloop Club Strawberry Festival (free) | Sun 12-5 PM | Beacon (Dutchess) | Family |
| Hudson Valley Renegades vs Jersey Shore (baseball) | Fri 7:05 / Sat 5:05 / Sun 2:05 | Heritage Financial Park, Fishkill (Dutchess) | Family |
| Edenville General Store Cruise-In (classic cars) | Thu 5:30-8:30 PM | Edenville, Warwick (Orange) | Family |
| Poughkeepsie Pride march & festival | Sat 12-4 PM | Poughkeepsie (Dutchess) | Family |
| Warwick Pride (free) | Sun 11 AM-3 PM | Warwick (Orange) | Family |
| Woodstock Pride Parade | Sun 1 PM | Woodstock (Ulster) | Family |
| Middletown / Warwick / Callicoon Farmers Markets | Sat & Sun | 3 counties | Family |
| Warwick Drive-In (3 screens) | Fri-Sun, dusk | 5 Warwick Tpke, Warwick | Family |
Strawberry fields and lineups can change with weather. Always confirm hours with the host before traveling.
For kids: where to take the little ones this weekend
The headliner for families with young kids is LEGOLAND New York in Goshen, open daily this time of year and running weekend hours of 10 AM to 5 PM on Saturday June 13 and Sunday June 14. Rides, build zones, and the Miniland model of New York landmarks make it the anchor of any Orange County kid weekend.
If you want something slower and hands-on, June is peak strawberry season, and the pick-your-own fields are open. Ochs Orchards at 4 Ochs Lane (Route 94) in Warwick is open daily 9 AM to 5 PM with strawberries plus early cherries. Lawrence Farms Orchards at 39 Colandrea Road in Newburgh is open daily for U-pick as well. Picking is weather-dependent and fields close once they are picked over, so call ahead or check the farm's social media the morning of. Only pay for what you pick, and the kids eat half of it in the field anyway.
For a rainy-hour backup or a calmer outing, the Hudson Highlands Nature Museum in Cornwall is a local favorite. The Wildlife Education Center has live native animals and indoor exhibits, and the Outdoor Discovery Center on Muser Drive has easy family trails and weekend nature programming. It is a gentle, low-cost way to spend a morning with curious kids.
For adults: winery music, craft beer, and a grown-up night out
The wineries and breweries are the heart of the adult weekend. Warwick Valley Winery & Distillery runs live music every weekend from 2 to 5 PM, with Dylan Doyle on Saturday June 13 and Soul Sense on Sunday June 14. No paid admission in June, so just show up, grab a glass, and find a spot on the lawn between Mt. Adam and Mt. Eve. Applewood Winery in Warwick has local musicians both Saturday and Sunday from 2 to 5 PM, paired with a wine tasting and hilltop views.
On the beer side, The Drowned Lands Brewery in Warwick, one of the most awarded breweries in New York State, hosts an all-day Summer Concert on the lawn Saturday June 13 from 12 to 7:30 PM, with Home.made Band, Dan Brother, and Pat C. The night before, they run their weekly Friday karaoke at 7 PM. Pennings Farm keeps the beer garden going with Moonshine Creek Friday from 6 to 9 PM and Alyssa Goldstein Sunday from 3 to 6 PM. For a Friday-night sports hang, Newburgh Brewing Company on the waterfront hosts a World Cup watch party with food and Hudson River views.
Prefer a tasting-room crawl? Brotherhood Winery in Washingtonville, America's oldest winery (1839), runs daily tours and tastings, and City Winery Hudson Valley in the historic Montgomery Mill pairs a restaurant and bar with a steady live-music calendar. Over in Ulster County, the tasting market at the Twin Star Fermentation Festival (see below) is a craft-beverage lover's dream.
For a bigger night out, Bethel Woods Center for the Arts in Sullivan County opens its season this weekend. Friday June 12 brings Jazz at Lincoln Center Presents John Pizzarelli, "Dear Mr. Bennett," at 8 PM. Sunday June 14 lands the marquee show: the True Colors Tour with Cyndi Lauper, The B-52s, Rosie O'Donnell, and Deborah Cox. Both are ticketed, so grab seats in advance. Closer to home, the Sugar Loaf Performing Arts Center in Orange County has Slippery When Wet, a Bon Jovi tribute, on Friday June 12.
For the whole family: festivals, parades, and farmers markets
This is where the weekend really shines. The Backpack Snack Attack Music Festival at Pennings Farm in Warwick runs Saturday June 13 from 12 to 8 PM with four bands (Fiddle Frenzy, Vinyl Tap, Sons of Hudson, and Jester's Edge), cider and food for the grown-ups, and farm space for the kids to roam. A $10 suggested donation supports the program that feeds local children on weekends.
In Ulster County, Twin Star Orchards in New Paltz hosts the 5th annual Hudson Valley Fermentation Festival on Saturday June 13. The farm is open and live music is free to all guests from 11 AM to 6 PM, while the tasting market of craft beverages and fermented foods runs in two ticketed sessions (1 to 3 PM and 4 to 6 PM). Up in Sullivan County, the Livingston Manor Trout Parade takes over Main Street starting at noon Saturday with this year's theme, Cirque du Trout. Now in its 20th year, it is one of the most photographed small-town parades in the Catskills, complete with vendors, music, and a chicken BBQ.
The St. Augustine's Bazaar, Food Truck and Music Festival in Highland is free all weekend (Friday through Sunday) with live music and a lineup of local food trucks. On Sunday June 14, the Beacon Sloop Club Strawberry Festival is a beloved free riverfront tradition just across the river in Beacon (Dutchess County), running noon to 5 PM with strawberry shortcake, two music stages, kids' activities, and a free sail on the sloop Woody Guthrie.
Sports fans have a full weekend too. The Hudson Valley Renegades host the Jersey Shore BlueClaws at Heritage Financial Park across all three days, with first pitch Friday at 7:05 PM, Saturday at 5:05 PM, and Sunday at 2:05 PM. Affordable minor-league baseball and a classic family night out, just across the river in Dutchess County.
It is also Pride weekend across the region. Saturday June 13 brings Poughkeepsie Pride, a march and festival from noon to 4 PM running down Main Street to Waryas Park in Dutchess County. On Sunday June 14, Warwick Pride runs 11 AM to 3 PM at the Warwick Valley Community Center (11 Hamilton Ave), a free, family-friendly afternoon of music, vendors, and community, and in Ulster County the Woodstock Pride Parade steps off at 1 PM from Comeau Drive. All three are welcoming, all-ages celebrations.
And do not skip the farmers markets. The Middletown Farmers Market runs Saturday 8 AM to 1 PM at Erie Way Park downtown. The Warwick Valley Farmers' Market, the largest in Orange County by vendor count, runs Sunday 9 AM to 2 PM at the South Street lot. The Callicoon Farmers Market in Sullivan County runs Sunday 11 AM to 2 PM at Callicoon Creek Park with 40-plus vendors along the Delaware River. Cap any night with a movie under the stars at the Warwick Drive-In (5 Warwick Tpke), open since 1950 with three screens, Friday through Sunday at dusk. Want to start early? The Edenville General Store Cruise-In in Warwick kicks off the weekend Thursday June 11 from 5:30 to 8:30 PM, with classic cars, weekly awards, raffles, and live music.
The bottom line
June 12-14, 2026 is a do-anything Hudson Valley weekend. Strawberry fields and LEGOLAND for the kids, winery and brewery music for the grown-ups, and festivals, parades, and farmers markets that pull the whole family together. If you are deciding between Orange, Ulster, and Sullivan County for your next home, this is the weekend to feel out what each one is like. Park the GPS, talk to the vendors, and notice which town keeps pulling you back. That is the one to call us about on Monday.
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Hudson Valley Weekend Events FAQ
What can families with kids do in Orange County NY this weekend?
LEGOLAND New York in Goshen is open Saturday and Sunday from 10 AM to 5 PM. June is peak strawberry season, so pick-your-own fields are open at Ochs Orchards in Warwick (daily 9 AM-5 PM) and Lawrence Farms Orchards in Newburgh. The Hudson Highlands Nature Museum in Cornwall has live native animals and easy family trails. The Backpack Snack Attack festival at Pennings Farm and the Beacon Sloop Club Strawberry Festival are both family favorites too, and Warwick Pride on Sunday is a free, family-friendly community celebration.
What is there for adults to do in the Hudson Valley June 12-14, 2026?
The wineries and breweries lead the adult weekend. Warwick Valley Winery has Dylan Doyle (Sat) and Soul Sense (Sun), 2 to 5 PM both days. Applewood Winery has live music Saturday and Sunday 2 to 5 PM. The Drowned Lands Brewery runs an all-day Summer Concert Saturday 12 to 7:30 PM and Friday karaoke at 7 PM. Pennings Farm has beer-garden music Friday and Sunday, Newburgh Brewing hosts a Friday World Cup watch party, and Brotherhood Winery and City Winery Hudson Valley round out the tasting-room options. For a bigger night out, Bethel Woods Center for the Arts opens its season with John Pizzarelli (Jazz at Lincoln Center) Friday June 12 and the True Colors Tour featuring Cyndi Lauper and The B-52s Sunday June 14.
What is the Backpack Snack Attack Music Festival at Pennings Farm?
It is an all-day live music event at Pennings Farm in Warwick on Saturday June 13, 2026 from 12 to 8 PM. The lineup features Fiddle Frenzy, Vinyl Tap, Sons of Hudson, and Jester's Edge, with a $10 suggested donation supporting the Backpack Snack Attack program that feeds local kids. Cider, food, and family farm activities round out the day.
Where can I go strawberry picking near Orange County NY in June 2026?
Ochs Orchards at 4 Ochs Lane (Route 94) in Warwick is open daily 9 AM to 5 PM with pick-your-own strawberries and early cherries. Lawrence Farms Orchards at 39 Colandrea Road in Newburgh also offers U-pick. Picking is weather-dependent and fields close once picked over, so call ahead or check the farm's social media the morning you plan to go. You pay only for what you pick, by the pound.
Are there farmers markets open in the Hudson Valley June 13-14, 2026?
Yes. The Middletown Farmers Market runs Saturday from 8 AM to 1 PM at Erie Way Park downtown. The Warwick Valley Farmers' Market, the largest in Orange County by vendor count, runs Sunday from 9 AM to 2 PM at the South Street lot. The Callicoon Farmers Market in Sullivan County runs Sunday from 11 AM to 2 PM at Callicoon Creek Park with 40-plus vendors.
Is June 14, 2026 Father's Day?
No. June 14, 2026 is Flag Day. Father's Day in 2026 falls on Sunday June 21. This weekend is a great early-summer window for strawberry picking, winery music, and festivals across Orange, Ulster, and Sullivan Counties.
How is the Orange County NY real estate market in June 2026?
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, Goshen, Middletown, Cornwall, and the Sullivan Catskills continue to draw strong buyer interest, and early June is one of the highest-traffic open-house windows of the year. The Caplicki Home Team can pull a free, data-driven home valuation in under a minute at caplickihometeam.com.
Sources: Pennings Farm Market (penningsfarmmarket.com), Warwick Valley Winery & Distillery (wvwinery.com), Applewood Winery (applewoodwinery.com), The Drowned Lands (drownedlands.beer), Twin Star Orchards (twinstarorchards.com), LEGOLAND New York (legoland.com/new-york), Ochs Orchards and Lawrence Farms Orchards, Hudson Highlands Nature Museum (hhnaturecenter.org), Sullivan Catskills (sullivancatskills.com), Orange County NY Farms (orangecountynyfarms.com), Beacon Sloop Club (beaconsloopclub.org). Confirm hours and lineups with each host before traveling.
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 brian@caplickihometeam.com.
