This past weekend was the annual Great Highwood Pumpkin Festival in downtown Highwood, and it was as exciting as usual.
This year was the 17th iteration of the free festival, which is the largest outdoor fall celebration on Chicago’s North Shore. The festival typically opens with a carnival on Thursday night and runs through Sunday, but this year’s rain pushed the festival opening to Friday.
The family-friendly event featured pumpkin carving, live music, pumpkin pie eating contests and much more. There are even costume contests for both children and pets – leashed dogs are allowed to attend.
One of the highlights of the festival is the lighting of the Great Pumpkin Wall – featuring up to 12,000 pumpkins. Because attendees can carve pumpkins and then add them to the wall, the lighting ceremony does not take place until Saturday night.
This year’s edition of the Pumpkin Festival also included special activities, such as “Curdtoberfest” from Culver’s and micro NASCAR racing – where participants drove around a NASCAR-style track in a racecar. The Culver’s Curdtoberfest area included the world’s first Dairy-Go-Round and a raffle to win a trip to Germany.
In previous years, the festival tried to surpass the Guinness World Record for the most jack-o’-lanterns carved and lit at the same time – the current record is 30,581 jack-o’-lanterns, set at a 2013 Pumpkin Festival in Keene, N.H. However, the event’s organizers decided to do away with the record attempt after warm weather made it difficult for the pumpkins to be kept cold enough to carve.
While the event was occurring, restaurants, bars and businesses around the festival area were open for attendees to wander in – creating a boost for local establishments.
This year’s festival benefited Service and Learning Together (SaLT), a nonprofit organization of volunteers who support food-insecure families, provide academic tutoring, help communities in crisis and more.


