Raw States
Great Highwood Pumpkin Fest
Highwood, IL · Quirky
- When
- October 1–4, 2026
- Where
- Downtown Highwood, Bank Ln · Highwood · IL
- Cost
- Not confirmed
- Status
- Confirmed from the organizer's published schedule
The Great Highwood Pumpkin Fest transforms downtown Highwood each October with pumpkin carving stations, illuminated pumpkin walls, and a Skeletons on Display exhibit of costumed skeleton figures around town. Now in its 16th year, it is billed as the North Shore's biggest outdoor fall celebration, with carnival rides, live music, and a pie eating contest. The festival is organized by Celebrate Highwood.
The history within reach
- Great Highwood Pumpkin Festsame spot
The Great Highwood Pumpkin Fest transforms downtown Highwood each October with pumpkin carving stations, illuminated pumpkin walls, and a Skeletons on Display exhibit of costumed skeleton figures around town.
A gunman fired from a rooftop into the Fourth of July parade here in 2022, killing seven people and wounding dozens on a street full of families with children.
Stews & Brews takes over Port Clinton Square in downtown Highland Park each October, with local restaurants serving soups, stews, and chili alongside craft beer sampling.
The glass box in the trees that Cameron Frye kicks his father's Ferrari out the back of, in John Hughes's 1986 comedy Ferris Bueller's Day Off, is a real modernist house in Highland Park.
- Ravinia3.2 mi
It started in 1904 as an amusement park built by a railway to give people a reason to ride the line out from Chicago, went bust, and came back as a music park.