Great Highwood Pumpkin Festival

Highwood’s pumpkin festival started as a run at the world record for lit jack-o’-lanterns and has become the North Shore’s biggest fall street party. According to the Daily Herald’s September 21, 2026 events roundup, the 2026 festival runs Thursday, October 1 through Sunday, October 4, opening with a community night Thursday from 4 to 9 p.m., then 4 to 10 p.m. Friday, noon to 10 p.m. Saturday and noon to 9 p.m. Sunday. Admission is free.

The organizer, Celebrate Highwood, sets up all-you-can-carve pumpkin stations, and finished pumpkins go up on two walls that are lit each night; the big Pumpkin Wall Lighting is Saturday at 7 p.m. The rest of the footprint covers City Hall at 17 Highwood Ave., Green Bay Road, Everts Park and the Metra station lot with carnival rides, hayrides, three stages of live music, kids’ and pet costume contests, a pie-eating contest, trick-or-treating and food and craft vendors. Carving costs $2 per pumpkin, and proceeds go to SaLT, a local nonprofit that feeds food-insecure families.

Green Bay Road closes from North Avenue to Highwood Avenue and Highwood Avenue closes from Green Bay to Waukegan Avenue for the weekend, per the organizer’s event map.

Plan your visit

Metra’s Union Pacific North line stops at Highwood, and the station parking lot is inside the festival, so the train is the obvious choice; it runs hourly on weekends and later on Saturday nights. Drivers coming up Sheridan Road or Green Bay Road will hit closures at North Avenue; park in Highland Park or Fort Sheridan and walk. Saturday from 5 p.m. through the 7 p.m. wall lighting is the crush, with lines at the carving tables. Thursday’s community night and Sunday afternoon are the easy visits with kids. Bring a jacket, cash for rides and carving, and a bag for the pumpkin you carve if you plan to take it home rather than donate it to the wall.