Highland WinterFest offers wagon rides, chili cook-off, kids’ activities and winter fun

Eliora Navarro-McKay of High Falls really loved the chili at the Highland WinterFest in 2017. (Photo by Lauren Thomas)

Snow or sleet, rain or shine, the 22nd annual Hudson Valley Rail Trail WinterFest will take place Saturday, January 12 from 11 a.m. to 2 p.m., offering plenty of reasons to get out and brave the cold. Festivities happen at the Hudson Valley Rail Trail Depot, located at 101 New Paltz Road in Highland. Admission costs $2 for adults, with children age 6 and under admitted free. Proceeds from the event benefit the Rail Trail’s upkeep.

The family-friendly winter festival draws in excess of 1,000 people most years, with attendance somewhat weather-related. (As of press time, the forecast is for cold and dry.) The community event is put on by the Hudson Valley Rail Trail Association (HVRTA) with the assistance of their many community volunteers.


The central event at WinterFest is the chili cook-off. Held under the Highland Rotary Pavilion, it features a gathering of several dozen volunteers manning crockpots full of chili donated by local eateries. Attendees may purchase two-ounce samples of the savory stew at a cost of 50 cents per, with an $8 “try them all” pass available. This year, there’s also something new: anyone who becomes a member of HVRTA at the event receives $10 in food tickets. 

Tasting is blind; even the volunteers dishing out the samples don’t know whose chili they’re serving. The winner receives bragging rights, with all revealed on social media in the days that follow the event. 

For those who don’t eat chili, there’ll be hot dogs and chips available as well as coffee, hot cocoa, bottled water and other snacks that will include toasted marshmallows.

Additional activities will include crafting in the children’s “Build a Project” tent sponsored by Lowe’s, with their staff on hand to assist and free tractor-drawn wagon rides on the Rail Trail. 

Any excess calories consumed sampling all those chilies can be walked off on the Rail Trail, of course, and the festivities also offer a chance to check out the old caboose located alongside the Pavilion, which will be open to visitors. The caboose is one of a series first built in 1915 with a steel body, replacing older wooden cabooses that were prone to fire. 

More information about the Hudson Valley Rail Trail Association is available at www.hudsonvalleyrailtrail.net and on their Facebook page.

There is one comment

  1. Rebecca A

    I think i’ll bring my step children next time, loved the wagon ride, it was a lil bumpy tho. lol. Will come back next year with my children doe.

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