Seasonal & Holidays

2022 Great Highwood Pumpkin Fest Benefits HP Community Foundation

The 12th annual festival kicks off Thursday with Community Appreciation Night.

Announcements from the Highland Park Community Foundation and ceremonial pumpkin wall lightings are planned Friday, Saturday and Sunday evenings.
Announcements from the Highland Park Community Foundation and ceremonial pumpkin wall lightings are planned Friday, Saturday and Sunday evenings. (Celebrate Highwood)

HIGHWOOD, IL — Four days of fall festivities in downtown Highwood begin Thursday evening as the 12th edition of the Great Highwood Pumpkin Fest gets underway.

The North Shore's largest annual outdoor Halloween-related event features nightly Jack-o-lantern lightings, carnival rides, multiple stages of live music, hay rides, food and beverage vendors and more, organizers announced.

This year's festival will benefit the Highland Park Community Foundation, which has been in the forefront of fundraising efforts on behalf of survivors and victims of the mass shooting at this year's July 4th parade.

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“We are thrilled to be the beneficiary of this year’s Pumpkin Fest as it comes at the perfect time for the HPCF to refocus its fundraising efforts on our General Fund," Betsy Brint, chair of the foundation, said in a statement. "As we close the 4th Fund we want to return to our organization's roots of granting money to nonprofits that provide educational, social service, and cultural programs for Highland Park and Highwood residents."

While the 2020 pumpkin fest was canceled due to COVID-19, a new Highwood tradition began, as hundreds of life-sized skeletons were placed around town in what was dubbed the "Great Highwood Skeleton Invasion."

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This year, the pumpkin fest will for the first time feature an interactive "Skeletons on Display." According to organizers, each display will feature a skeleton versions of dance scene or moment from pop culture or film, with digital music to accompany each scene.


Attendees at the 2021 Great Highwood Pumpkin Fest pose for a photo near a skeleton display. (Celebrate Highwood)

Although the official opening of the fest is not until 4 p.m. the following day, attendees at Thursday's Community Appreciation Night will have a change to get discounted unlimited carnival rides for $30, according to organizers.

Community groups will be on site at three "all-you-can-carve" pumpkin stations in Everts Park, City Hall Park and Painters Park, along with live music and a full bar at Painters Park, 424 Sheridan Road.

Live music is scheduled from 4 to 10 p.m. Friday, from 11 a.m. to 10 p.m. Saturday and from noon to 8 p.m. Sunday across three stages — a main stage located on Green Bay Road at North Avenue, a world music stage at Everts Park Bandshell and a local music and activity stage in Painters Park.

Other highlights of the festival include trick or treating throughout the festival grounds from 4 to 6 p.m. Friday followed by a ceremonial pumpkin wall lighting at 7:45 p.m. and Sunday afternoon contests for best pet costume, best kids costume and pumpkin pie eating.

And this year's Superhero 5K Family Fun Run, Walk & Stroll starts at 9 a.m. Saturday. Participants are encouraged to come dressed as their favorite superhero — whether a character from comic books or an inspirational figure from reality

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