Chili when it’s chilly: WinterFest returns to Highland (with photos)

The annual WinterFest celebration returned to Highland last Saturday, January 14, offering family-friendly reasons to get out and brave the cold. Temperatures were seasonal but there was no snow, which may be why the parking lot filled up so fast and many visitors found themselves parking up and down New Paltz Road.

The festival’s “Best of Fest” Chili Cook-Off is reason enough to go. Seventeen local eateries, including some new entrants, donated several gallons of chili each to be dished out from slowcookers stationed under the Hudson Valley Rail Trail Pavilion. The pots of savory stew were manned by volunteers, mainly members of Highland Rotary Club. 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.

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


The restaurants from Highland, New Paltz and other nearby areas that participated in the competition were Bagels & Bites, El Paso, Gateway Diner, Main Street Bistro, The Gilded Otter, Mahoney’s, On A Roll Deli, P&G’s, Pavesi’s, Perch, Sal’s, The Cake Artist, The Would, The Sandwich Shop, Three Guys, Underground Coffee & Ales and Wagon Wheels Deli.

Coming out on top with first place honors was Sal’s Place (pot number 28 for those who were wondering). On A Roll Deli (pot 21) took second place, with Wagon Wheels Deli (pot 29) placing third in the people’s choice.

If unlimited chili tasting wasn’t enough to entice, WinterFest also offered tractor-pulled hay wagon rides up and down the Rail Trail — courtesy of Dave DuBois of DuBois Farms — a fire pit to roast marshmallows over, a kids’ activity tent sponsored by Lowe’s — who supplied the materials and assistance to help kids create small wooden toys — lawn games organized by Boy Scout troops 70 and 193 and a karaoke machine, the perennial favorite of teenage girls. Members of the Highland High School Interact Club (a junior version of Rotary Club) were on hand to assist with parking and other organizational details.

The circa 1915 caboose next to the pavilion was open to visitors, too. WinterFest is one of the few times people can go inside and check it out. (The 1926 N5 caboose at 75 Haviland Road, where Walkway Over the Hudson terminates at the entrance to Highland, has been converted into an information kiosk and equipped with exhibits on local railroad-related history. It’s open to the public on weekends, spring through fall.)

As many as 1,000 people come to WinterFest every year, with the small town appeal of the event drawing families who want to get out in the winter chill and enjoy some time together without having to travel far or spend a lot of money. The crowd included teens in groups, couples, families with little ones and even some solo chili-chowing-down by athletic-gear-garbed runners accompanied by dogs wearing coats.

WinterFest is one of a number of events sponsored by the Hudson Valley Rail Trail Association (HVRTA) throughout the year, with all proceeds from the event benefitting the maintenance of the Rail Trail and improvements to it.

The HVRTA meets on the third Tuesday of each month. Meetings are 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 its beginnings and more helping hands will always be essential as the Rail Trail expands in the coming years.

Next on the horizon is expansion of the Highland trail from its current terminus at Tony Williams Park to the intersection of New Paltz Road and Route 299 (by Lowe’s). Eventually, the plan is to connect with the Wallkill Rail Trail and beyond, creating an extensive Ulster County Trail Network.

More information about the Hudson Valley Rail Trail Association is available at and on their Facebook page, which lists the pot numbers associated with each restaurant for those who enjoyed a particular chili at WinterFest and wish to know where to go to purchase it again.