3 Family-Friendly Events for Kids in New Paltz This October 2026 |
From pickles to haunted trails to Halloween art — here's what's happening for families this fall |
October in New Paltz means crisp air, changing leaves, and a packed calendar of community events that bring families together. Whether your kids love quirky festivals, spooky adventures, or getting creative, there's something for every age group this month. Here are three can't-miss events for families with children.
29th Annual Rosendale International Pickle Festival
When: Sunday, October 18, 2026 | 10 AM – 5 PM
The Rosendale International Pickle Festival is one of the Hudson Valley's most unique and beloved fall traditions — and it's perfect for families. Kids under 12 get in free, and the festival offers something for everyone: over 100 vendors selling pickles, crafts, food, and jewelry, plus the famous Pickle Triathlon featuring a pickle eating contest, pickle juice drinking competition, and pickle toss.
Up to 7,000 people attend this rain-or-shine event every year, and all proceeds are donated back into the Rosendale community. It's a great opportunity to introduce kids to local artisans, sample unusual foods, and enjoy a day of quirky small-town fun. The festival runs from 10 AM to 5 PM, and ATMs are available on site (though the ticket booth is cash only).
6th Annual Creepy Hollow Haunted Trail
When: Friday, October 23; Saturday, October 24; Friday, October 30; Saturday, October 31, 2026 | 7 PM – 9 PM
If your kids love a good scare (or at least think they do), Creepy Hollow Haunted Trail is back for its sixth year with four nights of Halloween thrills. The family-friendly haunted trail winds through the woods at 4 Carolyn Drive in New Paltz, offering a spooky but age-appropriate experience for children and teens.
The trail runs from 7 PM to 9 PM on all four nights, giving families flexibility to choose a date that works. It's a local Halloween tradition that keeps getting better each year — and it's right in town, so no long drive for a seasonal adventure. Bring the whole family and see if you're brave enough to make it through Creepy Hollow.
3rd Annual Halloween & Harvest Window Painting
When: Saturday, October 22, 2026 | 11 AM – 2 PM (Rain date: Sunday, October 23)
The Town of New Paltz's Office for Community Wellness is sponsoring the third annual Halloween & Harvest Window Painting Project, and it's open to kids, teens, adults, and families. Participants create window designs in advance, aligned with this year's Halloween or Harvest themes, and display them around town.
This is a creative, community-building event that lets kids contribute to the town's seasonal atmosphere while developing their artistic skills. Registration is required by September 30 — contact Phoenix at (845) 256-5014 or pkawamoto@townofnewpaltz.org for more information and to sign up.
Plan Your October
With the Pickle Festival on October 18, Window Painting on October 22, Creepy Hollow on October 23-24 and 30-31, there's no shortage of family fun in New Paltz this month. Mark your calendars, grab your costumes, and enjoy everything fall has to offer in the Hudson Valley. |
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Love that the pickle festival donates all proceeds back into the Rosendale community. Nice to see a big event actually keeping the money local instead of it disappearing somewhere else.
Carol JenningsSame, it makes such a difference when you know the money is actually staying in the community. Rosendale is a small town that could really use it.
Rosendale Pickle Festival being rain or shine is key. October weather up here is so unpredictable. Went in the rain one year and honestly it was still worth it, just bring layers.
Mike_PaltzWent in the rain a few years back too and honestly the vendors are really committed, most of them stayed set up the whole time. Just bring an umbrella and you are fine.
The window painting project sounds really cool but the registration deadline is September 30 and October 22 is the event date. Wish they gave more notice so people could actually plan ahead.
Bri SantanaYeah September 30 is really tight. If you have a kid who wants to participate you need to plan the design, get materials, and register all before the deadline. A little more lead time would help a lot.
Creepy Hollow is great but just a heads up for parents with little ones, my 7 year old was NOT okay last year. The woods section at night is genuinely pretty scary. Probably better for middle school and up.
TomaszW_NPGood to know, thank you! My daughter is 8 and she gets spooked pretty easily. Might wait another year or two before we try it.
We did the Pickle Festival two years ago and my kids still talk about the pickle toss. Definitely go early though, parking fills up fast and the crowds get intense by noon.
Donna R.The early arrival tip is so real. We showed up around 11 last year and spent forever just looking for parking. Next time we are getting there right at 10.