Whitefish Bay's Great Pumpkin Festival: Fall 2025 Guide
The Whitefish Bay Civic Foundation’s Great Pumpkin Festival returns Wednesday, October 28 through Saturday, October 31, 2026.
The festival runs from 6–9 p.m. each night at Old Schoolhouse Park, across from the Whitefish Bay Public Library. Admission is free.
2026 Great Pumpkin Festival Details
Dates: Wednesday, October 28–Saturday, October 31, 2026
Hours: 6–9 p.m. nightly
Location: Old Schoolhouse Park in Whitefish Bay
Admission: Free
The centerpiece of the festival is a glowing display of community-carved jack-o’-lanterns. Families can pick up pumpkins, carve them at home and return the finished creations to the park before the festival begins Wednesday, October 28.
Once illuminated, the rows of carved pumpkins transform Old Schoolhouse Park into one of the Milwaukee area’s most memorable Halloween displays.
The official 2026 calendar confirms that the festival will also feature live music, food and a beer tent each evening from 6–9 p.m.
How to Add Your Pumpkin to the Display
Participating is part of the fun:
Pick up a pumpkin from Old Schoolhouse Park during the designated distribution period.
Take it home and carve your design.
Return the carved pumpkin before Wednesday, October 28.
Come back after dark to find your creation among the illuminated display.
The Whitefish Bay Civic Foundation has not yet announced the 2026 pumpkin pickup schedule. Check the organization’s official event calendar or Facebook page as the festival approaches.
2026 Live Music Schedule
Live music is scheduled for all four nights, but the individual performers have not yet been announced.
Wednesday, October 28: To be announced
Thursday, October 29: To be announced
Friday, October 30: To be announced
Saturday, October 31: To be announced
We’ll update this guide when the Whitefish Bay Civic Foundation releases the complete entertainment lineup.
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.
Tips for Visiting with Kids
Arrive shortly after sunset. The pumpkins are most impressive after dark, but visiting early in the evening can help families with younger children avoid the largest crowds.
Dress for late-October weather. The event takes place outdoors, so bring warm layers, hats and gloves when temperatures dip.
Bring a stroller carefully. Old Schoolhouse Park is manageable with a stroller, although crowds and uneven grassy areas can make navigating more difficult.
Expect limited nearby parking. Street parking is available around the park, but the closest spaces can fill quickly on Friday and Saturday nights.
Bring a flashlight. A small flashlight can be useful when walking back to your vehicle, especially with children.
Consider a weeknight visit. Wednesday and Thursday may offer a more relaxed experience than Halloween weekend.
Whitefish Bay Civic Foundation 2026 Calendar
The Great Pumpkin Festival concludes another busy year of community celebrations organized by the Whitefish Bay Civic Foundation:
May 2: Green Day in the Bay
May 25: Memorial Day Ceremony
July 4: Whitefish Bay Fourth of July Parade and Celebration
July 19: World Cup Final Watch Party
August 15: Sounds of Summer
September 2: Ice Cream Social
October 28–31: Great Pumpkin Festival
Dates and details are available through the Whitefish Bay Civic Foundation’s official 2026 calendar.
Make It a Halloween Outing
The final day of the 2026 festival falls on Halloween. The Merchants of Whitefish Bay have also listed downtown trick-or-treating for Saturday, October 24, from 10 a.m.–noon—one week before Halloween and the festival’s final night.
Related seasonal activities: