Reporting by Nickie Hayes, Poughkeepsie Journal
There are a handful of essential summer experiences in the mid-Hudson Valley — the fairs, festivals and activities you have to do during the warm weather months.
These summer can’t-miss events are traditions for some, but if you haven’t given them a shot yet, here’s your curated reminder.
Whether it’s getting outdoors, trying new foods or dressing up in costume that draws you in, you’ll find something on this list of fairs, festivals and classic summer affairs to add to your calendar this season.
One festival is even celebrating its 25th year in 2026.
Dutchess, Ulster and Orange county fairs
Orange County Fair: The 186th annual fair is the first and the longest of the three local county fairs in 2026, commencing on July 23 and going through Aug. 2. At 239 Wisner Ave. in Middletown, find rides, tribute bands performing live music, fireworks and a petting zoo.
Experience the Wild Wheels Thrill Show, or see Circus Murcia Big Top Circus, new to the Orange County Fair. Plus, for the returning grandstand shows, see a motocross exhibition, a monster truck show and a demolition derby.
For more information on what you can find at the Orange County Fair in 2026, including hours of operation and ticket pricing, visit orangecountyfair.com.
Ulster County Fair: This one is next up for the local county fairs, located at 249 Libertyville Road in New Paltz. The 139th annual event follows right after Orange County’s, beginning Aug. 4 and going until Aug. 9.
Enjoy Midway Rides, headliner live performances and entertainment, Robinson’s Racing Pigs, mobile arts, an aquatic acrobat show, a chainsaw carver, Disc-Connected K9s, a fireworks display, stilt walker Carrie McQueen, horse shows, along with the Ulster County Fair’s annual baby contest.
There is also a sensory-safe space for families with children who have autism or sensory sensitivities. Families can also borrow noise-canceling headphones, in child and adult sizes, for the day.
Visit ulstercountyfair.com for further information on tickets, hours of operation and all there is to do.
Dutchess County Fair: Last on the list for the local county fairs, the Dutchess event starts on Aug. 25 and goes through Aug. 30. For the 180th annual event, see live performances and entertainment at The Grandstand, agricultural shows and historic treasures, go on midway rides, and enjoy free entertainment such as Pawstars Frisbee Dogs, Dock Dogs, Rosaire’s Racing Pigs and stop by the Two by Two Animal Haven. Plus, purchase souvenirs, clothing and crafts from vendors and eat from more than 50 food vendors.
Find more information on what this year’s fair has to offer, ticket prices and hours of operation by visiting dutchessfair.com.
35th Hudson Valley Hot-Air Balloon Festival
Labor Day Weekend, Sept. 4-6, the 35th annual JPMorganChase Hudson Valley Hot-Air Balloon Festival is making its way back to Union Vale in Dutchess County. Over the course of the weekend, see five hot-air balloon ascensions with over 120 balloons taking flight. Each evening, see the balloons illuminated as fireworks light up the night sky.
Attendees have the opportunity to take flight once again in a hot-air balloon, whether that’s a morning or evening full flight for $350 each or tethered flight for $30 — the latter is only sold on site. As well, there’s a cash-only balloon walk, where you can go inside an inflated balloon anchored to the ground. Note these activities are wind- and weather-dependent.
Other experiences at the festival include a Two By Two Animal Haven’s “Wild World of Animal Show,” a drone obstacle course, sunrise yoga with the balloons, live music, lawn games, a children’s zone, family activities and a bubble zone.
There will also be food trucks and vendors, as well as Millbrook Vineyards & Winery’s wine and beer tent.
Tickets will only be sold online, in advance. There are no tickets sold at the gate. For 2026, there is a new VIP Experience Admission for those 21 and over at $175 per ticket.
Get all the specifics on this year’s itinerary and purchase tickets by visiting dcrcoc.org/balloonfesthv.org.
Pick-your-own sunflowers, sunflower festivals
Whether you want to pick your own sunflowers, go to a sunflower festival, take a great shot for social media or just enjoy the golden fields this August and September, the mid-Hudson Valley has options.
Here are some of the farms in Dutchess, Orange or Ulster counties:
- Barton Orchards, 63 Apple Tree Lane, Poughquag: Visit the farm for their eighth annual Sunflower Festival, running Aug. 28-30 and Sept. 4-7. Walk through the sunflower fields, take photos, catch live music, enjoy other activities on the farm or try the orchard’s craft hard cider. For more information, visit bartonorchards.com.
- Brittany Hollow Farm, 7141 Albany Post Road, Rhinebeck: Pick your own sunflowers at this farm as well as a wide variety of other flowers. Check out their Instagram page, @brittanyhollowfarmflowers, for updates on their picking season.
- Fishkill Farms, 9 Fishkill Farm Road, Hopewell Junction: Pick your own organic sunflowers starting in late August through September at this farm. For updates on when the sunflowers are in bloom, visit their Instagram page @fishkillfarms.
- Hudson Valley Cold Pressed Oils, 235 Sleight Plass Road, Pleasant Valley: Pick your own sunflowers in August during this farm’s ninth annual event Thursday-Sunday from Aug. 6 to Sept. 6. There’s free admission until 4:30 p.m. and afterward, it’s $5. Live music begins at 5:30 p.m. and sunflower picking ends at 7:30 p.m. For all the details on 2026’s event, visit hudsonvalleycoldpressedoils.com/events/.
- Jones Farm, 190 Angola Road, Cornwall: See sunflowers at this farm and get fresh-cut flowers of all kinds. Get updates on the farm on their Instagram page, @theshopsatjonesfarm.
- Kelder’s Farm, 5755 U.S. Route 209, Kerhonkson: From Aug. 9 to Sept. 1, enjoy the Sunflower Extravaganza Festival at Kelder’s Farm by exploring their 6-acre sunflower field and taking pictures. To find more information and purchase tickets, visit keldersfarm.com.
- Pierson’s Farm, 1448 state Route 211, Middletown: Pick your own sunflowers at this farm, typically beginning Labor Day weekend; check out their Sunflower Festival in September, too. For farm updates, visit their Facebook page, facebook.com/PiersonsFarm/.
- Sunflower Valley Farm, 366 county Road 12, New Hampton: This year, the farm will be opening July 24 to pick your own sunflowers, walk through the fields and experience their farm. For updates, including their summer event schedule featuring sunset events, a festival and drive-in movies at the farm, visit their Facebook page at facebook.com/SunflowerValleyFarm.
New York Renaissance Faire Weekends
Commencing Aug. 15 and continuing weekends through Oct. 4, immerse yourself in the realm of the New York Renaissance Faire, situated at 600 state Route 17A, Tuxedo, in Orange County. With people gearing up in armor and costumes, it feels as though you’re transported to the era.
A fan favorite and yearly staple for many, there is always plenty of entertainment, from jousting to Aaron Bonk’s Fire Whips and Swords show, vendors with artisan crafts, pubs scattered throughout, as well as games and rides to enjoy on a day at the fair.
For this year’s themed weekends, kick off the festivities with a “Marketplace Weekend” during opening weekend from Aug. 15-16. If you spend $500 in their marketplace, you’ll receive two tickets to return to the faire through Sept. 20. Aug. 22-23 will be “Cottagecore Weekend,” Aug. 29-30 will be a pirate-themed weekend, Labor Day weekend is going to be a time traveler-themed, Sept. 19 will be “Talk Like a Pirate Day” and the festivities will conclude with the “Harvest Ball” on Oct. 3-4.
There is something for everyone, from family-friendly shows to going on a group pub crawl with friends. To learn more about the 2026 New York Renaissance Faire, visit their website: renfair.com/ny/.
Drive-in movie theaters
If you’re looking for a classic summer activity, try going to your nearest drive-in movie theater.
In 1958, there were over 4,000 drive-in movie theaters across the U.S., but as of 2025, there were only 280, and 26 of them are in New York, according to the United Drive-in Theatre Owners Association.
However, Dutchess County appears to have one drive-in returning: the Hyde Park Drive-In.
For now, in the mid-Hudson Valley, locals can choose from four options. Here’s where to find a drive-in theater in the mid-Hudson Valley this summer:
- Fair Oaks Drive-in Theatre: 365 Bloomingburg Road, Middletown; fairoaksdriveintheatre.com
- Four Brothers Drive-in: 4957 state Route 22, Amenia; playeatdrink.com
- Overlook Drive-in Theatre: 126 Degarmo Road, Poughkeepsie; overlookdrivein.com
- Warwick Drive-In: 5 Warwick Turnpike, Warwick; warwickdrivein.com
There is also a drive-in theater in neighboring Columbia County: Hi-Way Drive-in Theatre, located at 10699 state Route 9W in Coxsackie.
Bonus: Look forward to the Hudson Valley Wine and Food Festival
Looking ahead to Sept. 12-13, get ready for the 25th Hudson Valley Wine & Food Festival at the Dutchess County Fairgrounds in Rhinebeck.
With New York wine and tasting experiences, craft beverages, local food, gourmet bites and chef and mixologist demonstrations, along with live music and over 300 vendors for shopping, there’s plenty to discover and try in the last days of summer at this festival.
Some local wine vendors that’ll be in attendance so far this year include C. Cassis, Milea Estate Vineyard and Millbrook Vineyards & Winery, all of Dutchess County; Ferreira Carpenter Estates Winery, Pazdar Winery, Rosina’s Winery and Warwick Valley Winery, of Orange County; and Bruynswick Winery, Freefall Sangria, Quartz Rock Vineyard, Whitecliff Vineyard, of Ulster County.
For all the details, like ticket pricing, vendors and entertainment, visit hudsonvalleywinefest.com.
Nickie Hayes is the Breaking & Trending News Reporter for the Poughkeepsie Journal and focuses on how to make the most of what the mid-Hudson Valley has to offer. See her most recent articles here. Contact reporter Nickie Hayes: NHayes@poughkee.gannett.com, 845-863-3518 and @nickieehayess on Instagram.
This article originally appeared on Poughkeepsie Journal.
