5 Family-Friendly Events in Ulster County This October 2026 |
From pumpkin train rides to pickle festivals, here's where to take the kids this fall |
October in Ulster County means crisp air, turning leaves, and a calendar packed with family-friendly festivals and activities. Whether you're looking for a spooky-but-not-too-scary Halloween adventure, a taste of Italian heritage, or a quirky local tradition, there's something for every age this month. Here are five can't-miss events happening across the county.
Headless Horseman Hayrides Children's Day
When: Saturday, October 3 and Saturday, October 17, 2026, 11:30 AM – 2:30 PM
If your little ones want a taste of Halloween without the nightmares, Children's Day at the Headless Horseman Hayrides is the perfect introduction to the season. All the monsters are friendly, and kids can enjoy a hayride, meet costumed characters, explore the Magic Moon Maze, wander through the Haunted Gardens, visit Witch Hazel's Halloween House, and check out the Dino Zone. Live music adds to the festive atmosphere. Rain dates are October 4 and October 18. Check the website for pricing details.
Ulster County 4-H Fall Fest
When: Saturday, October 10, 2026, 10:00 AM – 2:00 PM
Curious about what 4-H is all about? This free, drop-in event lets families explore the program through hands-on activities, one-on-one conversations with club members and volunteers, and up-close encounters with animals raised by 4-H youth. Kids can learn about everything from animal science to crafts, and everyone can enjoy a delicious 4-H milkshake from the Milkshake Booth. No registration required—just show up and explore.
Ulster County Italian American Festival
When: Sunday, October 11, 2026, 11:00 AM onwards
The Ulster County Italian American Foundation brings one of the Hudson Valley's largest celebrations of Italian heritage to Kingston's beautiful historic waterfront. Admission is free, and the festival features delicious Italian specialties, wine and beverages, live music, street performers, unique vendors, family-friendly activities, cultural presentations, and contests. Whether you come for the food, the music, the culture, or simply a wonderful day with family and friends, there's something for everyone. Bring the whole famiglia and stay for the celebration.
Catskill Mountain Railroad Pumpkin Express
When: October 17, 18, 24, and 25, 2026, with departures at 10:00 AM, 12:00 PM, 2:00 PM, and 4:00 PM
All aboard for a scenic fall adventure! The Pumpkin Express takes passengers on a 90-minute, 8-mile round-trip journey along the historic former Ulster & Delaware Railroad corridor. You'll meander through idyllic farmlands, glide across the Esopus Creek on the restored C9 Bridge, and roll through the Hurley Flats into the foothills of the Catskills. The best part? The train makes a stop at the Catskill Mountain Railroad's pumpkin patch, where each guest can pick out their own pumpkin to take home and decorate. Tickets are $25 for adults, $19 for children ages 2-12, $23 for seniors/military/veterans, and free for toddlers under 2 on a lap. Choose open-air flat cars or cozy coaches for the ride.
Rosendale International Pickle Festival
When: Sunday, October 18, 2026, 10:00 AM – 5:00 PM
Yes, there's a pickle festival—and it's been a Rosendale tradition since 1997. The 29th Annual Rosendale International Pickle Festival brings over 100 vendors selling pickles, groceries, hot food, baked goods, crafts, fashion, jewelry, and more. Kids under 12 get in free (adults are $5, cash only at the ticket booth). The festival features a home pickling contest and the infamous Pickle Triathlon, which includes a pickle eating contest, pickle juice drinking, and a pickle toss. Up to 7,000 people attend this quirky celebration each year, and all proceeds are donated back into the Rosendale community. The festival runs rain or shine, and ATMs are available on site.
Plan Your Fall Fun
October is the perfect time to get out and enjoy Ulster County's vibrant fall season. Whether you're riding the rails to pick a pumpkin, celebrating Italian heritage on the waterfront, or watching your kids try their first pickle-eating contest, these events offer something for every family. Mark your calendars, grab your flannel, and make some autumn memories. |
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Didn't know the 4-H Fall Fest was free and no registration needed. That is perfect for us, we never plan ahead. Definitely stopping by the milkshake booth.
Carla BonfiglioSame, we are total last minute people. It's so rare to find something family friendly that you can just show up to without booking anything weeks in advance. We'll be there.
25 dollars a head for the Pumpkin Express adds up fast with a family of four. Wish they had a family rate. The ride sounds beautiful though.
Tom GrabowskiI hear you, it does add up. Though kids under 2 ride free which helped us a little when ours were small. Maybe pack your own snacks and make a full day of it to get the most out of the cost.
The pickle triathlon is real and it is absolutely unhinged. My neighbor did the pickle juice drinking contest in 2023 and I still think about it. Would 100% recommend watching even if you don't compete.
Patrice L.The pickle juice drinking is something else. My cousin did it a few years ago and said it was way harder than it looked. The crowd going wild for it made the whole thing even funnier to watch.
Took the Pumpkin Express a couple years back with my nephew. Crossing over the Esopus Creek on that old bridge is honestly really cool. Worth every penny especially for little kids.
mike_rkThat bridge crossing is my favorite part too. Something about going over the water with the fall colors around you feels really special. Glad they kept that stretch of the line running.
The Italian American Festival on the waterfront is always such a good time. Been going for years and the food alone is worth the trip. Glad it made the list!
Donna FerrareseAgreed, the food vendors are great. Last year I got a cannoli that was honestly one of the best I've ever had and I grew up in an Italian household so that's saying something.