Milwaukee-area families have plenty of ways to celebrate pumpkin season, from an all-day farm festival to community carving events and illuminated displays.
Whitefish Bay’s Great Pumpkin Festival returns October 28–31, 2026, and Bay View Pumpkin Pavilion runs October 21–24. You’ll also find Basse’s Farms Pumpkin Fest and Bayside’s Pop-Up Pumpkin Party below.
Check the event organizer’s official page again shortly before your visit. Weather, crop conditions, ticket availability and community-event schedules can change.
2026 Milwaukee-Area Pumpkin Festival Guide
Confirmed for 2026
Basse’s Farms Pumpkin Fest — Colgate
Dates: September 18–November 1, 2026
Hours: Friday–Sunday, 10 a.m.–6 p.m.; Monday and Thursday, noon–6 p.m.; closed Tuesday and Wednesday; last admission at 5 p.m.
Published admission: $14.99 plus tax Monday/Thursday; $17.99 plus tax Friday–Sunday in September; $23.99 plus tax Friday–Sunday in October; children under 2 free
Location: 3190 County Road Q, Colgate
Basse’s has published the most complete 2026 schedule in this guide. The farm advertises more than 65 attractions, including an 8-acre corn maze, a smaller mystery maze, farm animals and a large pumpkin-picking area. Some attractions may have limited operating times.
Basse’s is cashless at points of sale. Guests carrying cash can convert it to a gift card at the farm. Check the current Pumpkin Fest page before leaving home for ticket availability and weather notices.
Bayside Pop-Up Pumpkin Party — Bayside
Date: Sunday, October 25, 2026
Time: 1–5 p.m.
Location: Ellsworth Park
Bayside’s Pop-Up Pumpkin Party has a confirmed 2026 date and is a convenient North Shore option. Because activity details can change, check the Village of Bayside’s current event information before attending.
Whitefish Bay Great Pumpkin Festival
Dates: October 28–31, 2026. Location: Old Schoolhouse Park. Bring a pumpkin carved at home for the community display, and check the Whitefish Bay Civic Foundation’s event calendar for current nightly details and participation instructions.
Bay View Pumpkin Pavilion
Dates: October 21–24, 2026. Location: Humboldt Park Pavilion. This community tradition includes pumpkin carving, a display of illuminated pumpkins, live music and local food. Check the Bay View Neighborhood Association’s Pumpkin Pavilion page for the daily program.
Popular festivals awaiting final 2026 details
Hallowings in Greendale
Greendale’s multi-day Halloween celebration frequently includes carved pumpkins and family activities in the village center. The specific 2026 program, dates and hours were still pending at this update. Confirm details with the Village of Greendale or its official tourism channels.
Thiensville Applefest and other harvest events
Applefest and several nearby harvest celebrations sometimes include pumpkin activities, but they are not interchangeable with dedicated pumpkin festivals. Their 2026 schedules were not confirmed for this update, so the old dates have been removed. Use each organizer’s official calendar for the final program.
How to use this guide
Check each organizer’s current page before visiting for the latest schedule.
Before leaving home, recheck weather, parking, admission, ticket requirements and whether pumpkins or carving supplies are provided. Outdoor fall events can change quickly because of weather or crop conditions.
More fall family guides
Pumpkin Picking Near Milwaukee: 2026 Family Guide
Milwaukee Pumpkin Paradise 2026
Best Corn Mazes Near Milwaukee: 2026 Family Guide
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