Whitefish Bay's Great Pumpkin Festival: Fall 2025 Guide
The Great Pumpkin Festival, presented by the Whitefish Bay Civic Foundation, returns this year on Wednesday, October 22 through Saturday, October 25, 2025.
The festival runs each night from 6-9 pm at Old School House Park, right across from the library.
Here's how it works: families pick up their pumpkins and take them home to carve, allowing creativity to flourish in the comfort of their own kitchens and dining rooms.
Then, before Wednesday, October 22, everyone brings their carved masterpieces back to the park to become part of a breathtaking community pumpkin display that transforms the entire area into a glowing autumn wonderland.
While the carved pumpkins are undoubtedly the stars of the show, the festival offers so much more for families looking to embrace the season: Each evening features live music that fills the air with festive melodies, while the Jack Pandl’s Whitefish Bay Inn food tent serves up spooky favorites. Vendors also provide pretzels, beer, wine and soda.
This year’s music line-up includes:
Wednesday, 10/22: Pat McCurdy
Thursday, 10/23: The Hungry Williams
Friday, 10/24: Bigger Boat
Saturday, 10/25: Suzie and The Detonators
Great Pumpkin festival music
The Pumpkin Fest Origin and Spread
Did you know that the Great Pumpkin Festival all began with one man’s backyard?
Local legend Gordy Falk (a.k.a. “The Pumpkin Man”) started carving pumpkins in the mid-1970s and soon attracted so much attention to his Carlisle Avenue lawn that police asked him to move the display!
Falk briefly moved the show to Wisconsin State Fair Park, and eventually reached an agreement to display his pumpkins at the The Bavarian Inn. His huge display was moved to Old Schoolhouse Park in the late 1980s, where the Whitefish Bay Civic Foundation stepped in to help turn it into the official annual community festival.
The tradition has now even inspired and spread to another Bay, with the Bay View neighborhood hosting the annual Pumpkin Pavilion.
Today, the event draws families from across the North Shore with pumpkin-carving, live music, food vendors and more—and you can even watch Gordy in his own carving tutorial on YouTube.
Save the Dates
The Great Pumpkin Festival is the culmination of the Whitefish Bay Civic Foundation’s annual festivities. Here’s what is included in the full 2025 calendar for the community:
May 3: Green Day in the Bay
May 26: Memorial Day
June 18: Ice Cream Social
July 4: Parade and Celebration
August 6: Ice Cream Social
August 16: Sounds of Summer
October 22-25: Great Pumpkin Festival
Looking for more area fall festivals and Halloween activities? We have you covered:
Racine Zoo’s Jack-O’-Lantern Nights, Oct 2–31
Complete guide to Greater Milwakuee area trick or treating schedule