This is the North Shore's signature fall street festival: whole blocks of Highwood given over to pumpkin walls, carving stations, a carnival and two music stages. Saturday's 7pm lighting of the Great Pumpkin Wall is the moment to aim for. Sunday adds pet and kids' costume contests and a pumpkin pie eating contest.
What to expect
Crowded, family-heavy streets in a small downtown, with food and craft vendors, community pumpkin carving, and carnival rides in the Metra station lot. Live music runs at Everts Park Pavilion and the J. Blanton Main Stage. Friday opens with trick-or-treating across the grounds from 4 to 6pm.
Good to know
- Hours: Friday 4–10pm, Saturday noon–10pm, Sunday noon–9pm.
- The Great Pumpkin Wall lighting is Saturday at 7pm.
- Sunday contests at City Hall lot: pets at noon, kids' costumes at 1pm, pumpkin pie eating at 2pm.
- The carnival is in the Highwood Metra station lot on the Union Pacific North line.
- A community night and opening carnival runs Thursday, October 1, 4–9pm.
Going? Keep it.
Also in Far Suburbs
More festivals that weekend
Common questions
When is the Great Highwood Pumpkin Festival?
October 2–4, 2026, with an opening community night on Thursday, October 1.
How do I get there without a car?
Take Metra's Union Pacific North line to Highwood; the carnival is in the station lot.