What Are the Best Things to Do in Orange, Ulster, Sullivan & Dutchess County, NY This Father's Day Weekend? (June 19-21, 2026)
By Brian Caplicki · Caplicki Home Team · Updated June 16, 2026 · 8 min read
Juneteenth Friday, a full Saturday, and Father's Day Sunday give the Hudson Valley one of its biggest weekends of early summer. Here is a verified, town-by-town guide across Orange, Ulster, Sullivan, and Dutchess County, NY.
Quick Answer
The standout events this weekend are the Beacon Juneteenth Riverfront Festival on Friday June 19, the Strawberry Jam-Boree in Goshen and the Faith and Fuel Car Show in Warwick on Saturday June 20, the Deep Water Literary Festival in Narrowsburg all three days, Yacht Rock Revue at Bethel Woods on Saturday night, and live weekend music at Pennings Farm, Warwick Valley Winery, and Applewood Winery. Sunday June 21 is Father's Day, with a seasonal brunch at All One One All Farm in Goshen, a Father's Day barbecue at Lasting Joy Brewery in Tivoli, and afternoon music across the wineries. Saturday farmers markets run in New Paltz, Kingston, Middletown, Narrowsburg, and Rhinebeck.
Weekend at a Glance
| Day | Event | Where | Time | Cost |
|---|---|---|---|---|
| Fri 6/19 | Juneteenth Riverfront Festival | Seeger Riverfront Park, Beacon (Dutchess) | 11 AM-5 PM | Free |
| Fri 6/19 | Deep Water Literary Festival opens | Narrowsburg (Sullivan) | All day | Many free; $15 marquee |
| Fri 6/19 | Free Shrimp Band (live music) | Pennings Farm, Warwick (Orange) | 5-8 PM | $5 cover |
| Sat 6/20 | Strawberry Jam-Boree | All One One All Farm, Goshen (Orange) | 12-1:30 PM | Taster ticket |
| Sat 6/20 | Faith and Fuel Car Show | Kings Elementary, Warwick (Orange) | From 10 AM | Free community event |
| Sat 6/20 | OC5 Sunset Series (live music) | Pennings Cidery, Warwick (Orange) | 5-8 PM | $10 cover |
| Sat 6/20 | Yacht Rock Revue: PRIMETIME | Bethel Woods, Bethel (Sullivan) | 7:30 PM | Ticketed |
| Sat 6/20 | Slam Allen Band & Bruce Katz Band | Towne Crier Cafe, Beacon (Dutchess) | 8:30 PM | Ticketed |
| Sun 6/21 | Father's Day seasonal brunch | All One One All Farm, Goshen (Orange) | 11:30 AM & 2 PM | Ticketed seating |
| Sun 6/21 | Father's Day BBQ + DJ Pete Pop | Lasting Joy Brewery, Tivoli (Dutchess) | 1-7 PM | Free entry |
| Sun 6/21 | Father's Day Brunch Cruise (Solaris) | Maritime Museum, Kingston (Ulster) | Book ahead | Ticketed |
| Sun 6/21 | Deep Chemistry (live music) | Pennings Farm, Warwick (Orange) | 3-6 PM | Free |
| Sat & Sun | Winery live music | Warwick Valley Winery & Applewood (Orange) | 2-5 PM | Free admission |
Confirm dates, times, and tickets with each venue before you go. Full details by county below.
This is a rare three-in-one weekend. Juneteenth falls on Friday June 19, Saturday June 20 is packed, and Sunday June 21 is Father's Day. If you are house hunting in the Hudson Valley, weekends like this are also the best way to get a feel for a town before you ever make an offer. Below is everything we could verify, organized by county, so you can plan around Goshen, Warwick, Narrowsburg, New Paltz, or wherever the day takes you.
What is happening in Orange County, NY this weekend?
Strawberry Jam-Boree, Goshen. The 3rd Annual Seasonal Smackdown: Strawberry Jam-Boree takes over All One One All Farm in Goshen on Saturday June 20 from 12 to 1:30 PM. Home cooks bring their best homemade strawberry jam, made with locally grown strawberries, and compete for the title of AOOA 2026 Jam Master. If you are not competing, come as a taster, sample the jams, and cast your vote for the People's Choice winner. Expect raffles with jars from the master competitors plus goodies from local farms and celebrity chefs.
Faith and Fuel Car Show, Warwick. Car lovers should head to the Faith and Fuel Car Show on Saturday June 20 starting at 10 AM, at Kings Elementary School in Warwick, hosted by Echo Grace Church. It is a relaxed community gathering and a great Father's Day-weekend outing for anyone who loves classic and custom cars.
Live music at Pennings Farm, Warwick. Pennings Farm has music all three days. Friday June 19, Free Shrimp Band plays the Beer Garden from 5 to 8 PM with a 5 dollar cover. Saturday June 20, the Sunset Series brings OC5 to the Cidery from 5 to 8 PM with a 10 dollar cover. Sunday June 21, Deep Chemistry plays the Beer Garden from 3 to 6 PM. Pennings Farm Market is at 161 State Route 94 South, Warwick.
Warwick wineries. Warwick Valley Winery & Distillery hosts live music every weekend afternoon, typically 2 to 5 PM, rain or shine. A short drive away, Applewood Winery runs live music every Saturday and Sunday from 2 to 5 PM, May through October, weather permitting. Both are easy, low-key ways to spend a summer afternoon. Check each winery's site for this weekend's specific act before you head out.
Father's Day brunch, Goshen. All One One All Farm follows its Saturday jam contest with a Father's Day seasonal brunch on Sunday June 21, with seatings at 11:30 AM and 2 PM, built around fresh local ingredients.
Saturday farmers markets. The Middletown Farmers Market runs Saturdays from 8 AM to 1 PM at Erie Way Park on Union Street. Markets are an easy stop for local produce and a real read on a neighborhood's character if you are thinking about buying nearby.
Which breweries have events this weekend?
Drowned Lands Brewery, Warwick. The farm brewery at 251 State School Road in Warwick is a great Father's Day-weekend stop. Drowned Lands runs live music every Sunday, so Dad can settle in with a beer on June 21, and the taproom keeps a weekly rhythm of trivia and karaoke nights. Saturday hours run noon to 10 PM and Sunday 11 AM to 8 PM. Check their taproom events page for the exact Sunday act before you head out.
Father's Day at Lasting Joy Brewery, Tivoli. Over in Dutchess County, Lasting Joy Brewery at 485 Lasher Road in Tivoli is throwing a Father's Day celebration on Sunday June 21 with a special barbecue menu and DJ Pete Pop spinning vinyl from 1 to 7 PM. It is the one dedicated Father's Day brewery party we could confirm for the weekend.
Orange County's craft beer scene runs deep beyond these two. Clemson Bros. Brewery in Middletown, Rushing Duck and Long Lot Farm Brewery in Chester, Glenmere Brewing in Florida, and Equilibrium Brewery in Middletown are all open for the weekend. Check each brewery's site or social pages for live music or special programming, since taproom lineups are often posted just a few days out.
What is happening in Sullivan County, NY this weekend?
Deep Water Literary Festival, Narrowsburg. The eighth annual Deep Water Literary Festival runs Friday June 19 through Sunday June 21 in Narrowsburg, with this year's theme TIME SHIFT: stories that bend the clock. The 2026 lineup is a serious draw, featuring Joyce Carol Oates, Jad Abumrad, and Marlon James, plus immersive art installations and conversations across fiction, memoir, history, and performance. The festival is built to be open and accessible, with many free or by-donation events. Marquee conversations at the Tusten Theater, 210 Bridge Street, and the festival party are 15 dollars each, with discounts for multiple tickets and a limited number of Festival Passes.
Yacht Rock Revue at Bethel Woods. Saturday June 20 at 7:30 PM, Yacht Rock Revue brings its PRIMETIME show to Bethel Woods Center for the Arts in Bethel. It is a fun, sing-along night of smooth 70s and 80s hits. A bonus for music fans: James Taylor & His All-Star Band play Bethel Woods just before the weekend, on Thursday June 18 at 7:30 PM.
Narrowsburg Farmers Market. The Narrowsburg Farmers Market runs every Saturday, May through October, from 10 AM to 1 PM, and pairs perfectly with a Deep Water Festival visit.
What is happening in Ulster County, NY this weekend?
Live music in Woodstock. Woodstock's small venues stay busy all weekend. Listings show Joe P at Colony on Friday June 19 at 6 PM, Son Little playing CityFolk 2026 at Bearsville Theatre on Friday June 19 at 8 PM, Van Hayride at Colony on Saturday June 20 at 7 PM, and the Eugene Tyler Band at Colony on Sunday June 21 at 7 PM. Confirm show times and tickets directly with each venue before you go.
Revolutionary New Paltz. Revolutionary New Paltz is a two-month festival of family-friendly programs, tours, talks, dance classes, and exhibits running through July 4, honoring the town's history, people, place, and architecture. It is an easy add-on if you are already in New Paltz this weekend.
Father's Day Brunch Cruise, Kingston. The Hudson River Maritime Museum in Kingston runs Father's Day brunch cruises aboard Solaris, its 100 percent solar-powered tour boat, on Sunday June 21. Solaris cruises sell out, so book ahead and confirm the time directly at hrmm.org.
Father's Day at Mohonk, New Paltz. Mohonk Mountain House in New Paltz offers a Father's Day weekend package with golf, biking, archery, tomahawk throwing, corn hole, hiking, lake sports, live music, an outdoor barbecue, and a DIY wood-burned charcuterie board class. It is the splurge option for dads who like the outdoors.
Saturday farmers markets. The Hudson Valley Open Market in New Paltz runs every Saturday from 10 AM to 3 PM in the New Paltz Middle School parking lot, with farms, handmade goods, specialty foods, lunch, and live music. The Kingston Farmers Market runs Saturdays in Uptown Kingston with more than 50 local farms and food vendors.
What is happening in Dutchess County, NY this weekend?
Beacon Juneteenth Riverfront Festival. The fourth annual Juneteenth Riverfront Festival lands on Friday June 19 from 11 AM to 5 PM at Pete and Toshi Seeger Riverfront Park in Beacon. Expect live music, vendors, food, games, dancing, and performances in a free, family-friendly celebration on the water.
Live music at Towne Crier Cafe, Beacon. The Towne Crier Cafe at 379 Main Street in Beacon hosts the Slam Allen Band and the Bruce Katz Band on Saturday June 20 at 8:30 PM, a strong night of blues and roots music. Tickets through the venue.
Northern Dutchess Symphony Orchestra, Hyde Park. On Saturday June 20 at 7:30 PM, the Northern Dutchess Symphony Orchestra performs at the Marriott Pavilion at The Culinary Institute of America in Hyde Park, a polished option for a dressed-up evening out.
Father's Day at Lasting Joy Brewery, Tivoli. Lasting Joy Brewery at 485 Lasher Road in Tivoli celebrates Father's Day on Sunday June 21 with a special barbecue menu and DJ Pete Pop spinning vinyl from 1 to 7 PM. See the brewery section above for details.
Sunday farmers market. The Rhinebeck Farmers Market runs Sundays from 10 AM to 2 PM at 61 East Market Street, an easy Father's Day-morning stroll before brunch.
Where should you celebrate Father's Day in the Hudson Valley on June 21?
If Dad likes food, book the Father's Day brunch at All One One All Farm in Goshen at 11:30 AM or 2 PM. If he likes craft beer and a cookout, the Lasting Joy Brewery barbecue with a DJ in Tivoli runs from 1 to 7 PM. If he likes a relaxed afternoon with a drink and a band, Sunday music runs at Pennings Farm in Warwick from 3 to 6 PM and at Warwick Valley Winery and Applewood Winery from 2 to 5 PM. If he likes the outdoors and you want to make a full day of it, the Mohonk package in New Paltz covers everything from hiking to lawn games. If Dad likes being on the water, the Hudson River Maritime Museum runs Father's Day brunch cruises aboard the solar boat Solaris out of Kingston. And if Dad is a reader, close out the Deep Water Literary Festival in Narrowsburg on Sunday.
Thinking about buying or selling in one of these Hudson Valley towns?
A weekend like this is the best free market research you can get. Warwick, Goshen, Middletown, New Paltz, and Narrowsburg each have a distinct feel, and the only way to know which one fits is to spend a Saturday there. If you are selling, strong local events drive weekend foot traffic and out-of-area visitors who fall for a town and start searching for homes the same week, which is exactly when a well-prepared listing stands out. If you are buying, use these events to scout the commute, the downtown, and the weekend rhythm before you ever schedule a showing.
When you are ready, Brian Caplicki and the Caplicki Home Team know every zip code in Orange County, NY, from Warwick (10990) and Goshen (10924) to Middletown (10940 and 10941), Newburgh, Monroe, Chester, Montgomery, Cornwall, Washingtonville, Pine Bush, and Port Jervis, plus neighboring Ulster, Sullivan, and Dutchess County. That hyper-local knowledge is the difference between guessing and pricing, marketing, or buying with confidence.
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Hudson Valley Weekend FAQ
What is there to do in Orange County, NY this weekend (June 19-21, 2026)?
The biggest draws are the Strawberry Jam-Boree at All One One All Farm in Goshen on Saturday June 20 from 12 to 1:30 PM and the Faith and Fuel Car Show in Warwick on Saturday June 20 from 10 AM. Add live music all weekend at Pennings Farm and weekend afternoon music at Warwick Valley Winery and Applewood Winery. Sunday June 21 brings a Father's Day brunch at All One One All Farm.
What free events are happening in the Hudson Valley this weekend?
Many programs at the Deep Water Literary Festival in Narrowsburg are free or by donation. Saturday farmers markets in New Paltz, Kingston, Middletown, and Narrowsburg are free to browse, and the Faith and Fuel Car Show in Warwick is a community gathering.
Where can I celebrate Father's Day in Orange County, NY on June 21, 2026?
All One One All Farm in Goshen hosts a Father's Day seasonal brunch on Sunday June 21 at 11:30 AM and 2 PM. You can also catch Sunday afternoon live music at Pennings Farm, Warwick Valley Winery, and Applewood Winery in Warwick.
Is the Deep Water Literary Festival in Narrowsburg free?
The festival, June 19 to 21, 2026, is designed to be open and accessible with many free or by-donation events. Marquee conversations at the Tusten Theater and the festival party are 15 dollars each, with discounts for multiple tickets and a limited number of Festival Passes.
What time is live music at Pennings Farm in Warwick this weekend?
Free Shrimp Band plays the Beer Garden Friday June 19 from 5 to 8 PM (5 dollar cover), OC5 plays the Cidery Sunset Series Saturday June 20 from 5 to 8 PM (10 dollar cover), and Deep Chemistry plays the Beer Garden Sunday June 21 from 3 to 6 PM.
Which breweries have events this weekend in the Hudson Valley?
Drowned Lands Brewery in Warwick has live music every Sunday, including June 21. Lasting Joy Brewery in Tivoli hosts a Father's Day barbecue with DJ Pete Pop from 1 to 7 PM on Sunday June 21. Other Orange County taprooms, including Clemson Bros. in Middletown and Rushing Duck and Long Lot in Chester, are open all weekend; check each for live music posted close to the date.
Who is a good local realtor for every zip code in Orange County, NY?
Brian Caplicki and the Caplicki Home Team work every Orange County, NY zip code, from Warwick and Goshen to Middletown, Newburgh, Monroe, Chester, Montgomery, and Cornwall, plus neighboring Ulster and Sullivan County. They pair hyper-local market knowledge with full-service buyer and seller representation. Call 845-656-4498 or email brian@caplickihometeam.com.
What towns does the Caplicki Home Team serve in the Hudson Valley?
The team is based in Middletown, NY and serves all of Orange County, NY along with Ulster County, Sullivan County, Dutchess County, and the broader Hudson Valley.
Sources
Pennings Farm live music schedule (penningsfarmmarket.com) · Strawberry Jam-Boree, Eventbrite / All One One All Farm, Goshen · Faith and Fuel Car Show, Warwick (event listings) · Deep Water Literary Festival (deepwaterfestival.com, Chronogram) · Bethel Woods Center for the Arts event calendar · Warwick Valley Winery (wvwinery.com) and Applewood Winery (applewoodwinery.com) music pages · Drowned Lands Brewery (drownedlands.beer) and Lasting Joy Brewery (lastingjoybrewery.com) · Woodstock venue listings (Colony, Bearsville Theatre via Songkick / AllEvents) · Beacon Juneteenth Riverfront Festival (beaconny.gov) · Towne Crier Cafe (townecrier.com) · Northern Dutchess Symphony Orchestra at the CIA (destinationdutchess.com) · Hudson River Maritime Museum Solaris cruises (hrmm.org) · Revolutionary New Paltz and Mohonk Mountain House · New Paltz, Kingston, Middletown, Narrowsburg, and Rhinebeck farmers market pages. Event details can change. Confirm dates, times, and tickets with each venue before you go.
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.
