Hudson Valley Rail Trail WinterFest returns to Highland for 22nd annual chili cook-off

Highland Rotarian Rolf Oelgeschlager serves up chili at last Saturday’s annual WinterFest. (Photos by Lauren Thomas)

Loretta Miller remembers when the first Hudson Valley Rail Trail WinterFest was held in Highland. Organized by local bed-and-breakfast owners Jerry and Geri Luke, attendees back then sat at makeshift tables assembled from plywood and sawhorses. Twenty-two years later, WinterFest is still a pretty casual affair, but now has a permanent home under the sturdy Highland Rotary Pavilion, adjacent to the circa-1915 train caboose on the trail at 101 New Paltz Road.

The Lukes were founding members of the Hudson Valley Rail Trail Association (HVRTA). They came up with the idea of WinterFest as a way to raise funds for the maintenance of the trail, according to Miller, and the event became an annual tradition following the holiday season. Longtime members of the group that include Miller along with newer members of the HVRTA still volunteer to put on the now-annual event as a fundraiser for trail maintenance.


While toasting a marshmallow at last Saturday’s WinterFest in Highland, young Eamon Hamburger demonstrates the fact that saying “cheese” doesn’t necessarily make you smile.

The 2019 iteration of WinterFest held last Saturday, January 12, was a bit more streamlined than in years past, when the event included a kids’ tent, chainsaw wood carving and karaoke. The weather was quite cold, hovering in the 20s, but there were heaters under the Pavilion and fire pits for kids to toast marshmallows over, and the frigid cold seemed to have no effect on anyone’s enjoyment, especially those taking a ride on the tractor-pulled hay wagon up and down the trail, courtesy of Dave DuBois of DuBois Farms.

And the main focus of WinterFest — as usual — was on the “Best of Fest” Chili Cook-Off. Local eateries (and this year, some firehouses and community organizations) donated several gallons of chili each, to be dished out from slow-cookers stationed under the Pavilion. The pots of savory stew were manned by community volunteers, many of whom are connected in some way with HVRTA or the Highland Rotary Club, whose assistance with the event was much appreciated, according to HVRTA member Sue Van De Bogart. Hannaford supermarkets, as well as The Would restaurant, donated the additional supplies necessary to run a chili competition (spoons, napkins and such), she added, and The Would even allowed the HVRTA to use their kitchen to prepare a chili entry for the contest.

Two-ounce cups of chili could be purchased with tickets that cost 50 cents each, with a “try-them-all” ticket available for $8. Tickets could also be exchanged for hot dogs or cups of hot coffee and cocoa. Visitors who joined the HVRTA at the event received $5 in food tickets.

The tasting, as always, was done “blind,” with even the volunteers dishing out the samples unaware of who created the chili they were serving. Attendees were invited to vote for their favorite out of the many varieties available, which included mild, spicy and vegetarian options.

The chili was donated by Bagels & Bites, Brennie’s Pizza, Café Arts, Clintondale Fire Department, Farmers & Chefs (farm-to-table restaurant in Poughkeepsie), Coppola’s La Fantasia, El Paso Mexican restaurant, Gateway Diner, Hard Roll Deli, the Highland Hose Company of the Highland Fire District, Highland Landing Park Association, Hudson Valley Rail Trail Association, Main Street Bistro, Mahoney’s, On A Roll Deli, Sal’s Place, The Would, Three Guys, Underground Coffee & Ales and Wagon Wheels Deli. 

Folks wait on line for a sample of a popular entry in the Highland WinterFest chili competition last Saturday.

When all the votes were tallied, the winner in “Best of Fest” with first place bragging rights was Hard Roll Deli (pot #9). Bagels & Bites (pot #1) took second place, with The Would (pot #18) placing third.

WinterFest is one of a number of events sponsored by the Hudson Valley Rail Trail Association throughout the year, with all proceeds benefitting the Rail Trail’s maintenance and improvements to it. The group meets once a month, with meetings open to the public, held at Town of Lloyd Town Hall. New members are always welcome, since many of the board members have been active in the association since it began and more helping hands will always be essential as the Rail Trail expands in the coming years.

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

Michele Bennett and Dania Esposito of Highland attend the Highland WinterFest every year to sample the various offerings of competition chili recipes.