Have you ever attended an Event or Festival and wished that someone gave you some pointers before going? That’s how I felt the first time I went to the Hudson Valley Rail Trail WinterFest. And, you know what, this year I was better prepared and felt like a pro.

Hudson Valley Rail Trail Winterfest

The Hudson Valley Rail Trail WinterFest

Currently, in its 20th year, the Hudson Valley Rail Trail WinterFest brings together the local community for a fun-filled afternoon. The event takes place at 101 New Paltz Road in Highland, NY.

Although this is an outdoor event, the cold weather does not keep the locals away. Adults, teens, and children of all ages enjoy the yearly event. There were even some furry friends that braved the cold weather to enjoy the day with their owners. Lucky enough, this year, the sun was shining and there was no rain or snow in sight.


According to Hudson Valley Rail Trail Association President, Peter Bellizi, they are very proud to host this event for the community. Not only do people come out for the tractor-pulled har rides, but they also come out for the Annual Chili Contest. The event is a success because of the loyal volunteers: Hudson Valley Rail Trail Volunteers, Boy Scouts, Highland Rotary Club and the Highland High School Interact Club.


Hudson Valley Rail Trail

Hudson Valley Rail Trail  Hudson Valley Rail Trail Winterfest

Activities that take place at the Hudson Valley Rail Trail WinterFest

No WinterFest is complete without some marshmallow roasting. But in addition to marshmallows and chestnuts, the main event is the yearly Chili Contest. Showcasing local businesses, the Chili Contest is the highlight of the Festival for $0.50 per taste or $8.00 to sample them all, the Chili is not only a tasty treat, but it also keeps the hands and body’s warm. There are typically around 14-16 Entries in the chili contest, so there is a lot to choose from. Best of all, the visitors are the ones who vote for the favorite chili of the Festival.

In addition to the Chili, there is also other food for sale, such as hot dogs.

The day’s activities include hayrides, lawn games, and karaoke. There was no shortage of people enjoying the chili on this brisk day.

Hudson Valley Rail Trail Winterfest

Hudson Valley Rail Trail Winterfest

Hudson Valley Rail Trail Winterfest

The Best Thing You Can do at the Hudson Valley Rail Trail Winterfest Is…

Arrive on an empty stomach so you can taste and enjoy the chili, marshmallows, and chestnuts.

I love going to the WinterFest. Although I’m not a lover of cold weather, I do like to go and do fun things on the weekends. My time out there, this year, was short, but definitely enjoyable. I enjoyed entering the Caboose parked along the trail and keeping warm in between speaking to the patrons.

Hudson Valley Rail Trail Winterfest

This event not only showcasing an array of fantastic chilis from local establishments, but it also introduces others to and showcases the Hudson Valley Rail Trail. And that alone is worth the outing.

Make sure you check my Events Calendar, so you don’t miss this event next year!

Hudson Valley Rail Trail Winterfest


This visit to the WinterFest is part of my 52-week of creating lasting memories challenge. Download your copy of the list of ideas and pick your next adventure. It’s never to late to join me and have some fun this year! 


A Few Things to Know before Attending the Hudson Valley Rail Trail WinterFest: 

  • This event is perfect for anyone and everyone: Families, Adults only, Teen, Couples and is Pet-Friendly
  • The entrance fee to the event is $2.00/per person. Children under 6 years of age are free
  • Parking is FREE 
  • Season Information: This event occurs once a year
  • Entrance fee does not include food tickets: Chili tastings are $0.50/each or all for $8.00
  • Other food items are also available for sale
  • The event is Rain or Shine

For Additional and Updated Information,
Visit Their:

Facebook Page: www.facebook.com/hudsonvalley.railtrail/

The Hudson Valley Rail Trail WinterFest
101 New Paltz Road
Highland, NY

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Until the Next Adventure…

 

 

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