Looking for fall festivals in Lake Country and Waukesha County? We’ve rounded up the best family-friendly fall festivals, harvest celebrations, Oktoberfests, craft fairs, and community festivals happening throughout the area in 2026.
Last updated AUGUST 2026.
Discover the Best Fall Festivals in Lake Country & Waukesha County 
What You’ll Find in the 2026 Fall Fest Guide
- Family-friendly fall festivals
- Harvest festivals and community celebrations
- Oktoberfest events
- Craft fairs and vendor festivals
- Live music and entertainment
- Pumpkin and apple events
- Fall activities for kids
- Free and low-cost fall festivals
Fall is one of the busiest seasons for family events in Lake Country and Waukesha County. From Hartland and Oconomowoc to Delafield, Pewaukee, Waukesha and surrounding communities, local organizations fill September and October with fall festivals, harvest celebrations, Oktoberfests, craft fairs and family activities.
We’ve been rounding up family-friendly events in the Lake Country and Waukesha County area for years, and this guide is updated throughout the season as organizers announce new dates and details.
Keep scrolling to explore can’t-miss fall fun near Milwaukee, Madison, and right here in Lake Country—because fall only comes once a year, and you don’t want to miss a moment!
Please thank our Fall Festival Guide Sponsor:
Lake Country Dance
2026 Fall Festivals in Lake Country & Waukesha County
Browse 2026 fall festivals and harvest events in chronological order below. We’re continually adding new events and updating details as organizers release more information.
Holy Hill Art Farm Market
Bring your family to the Holy Hill Art Farm Market! Unique Rustic Marketplace ~ Featuring Artists an…
October 10 @ 9:00 am – 4:00 pmThe Faire at Prairie Hill Waldorf School
Prairie Hill Waldorf School is hosting The Faire at Prairie Hill October 10th from 9am to 3pm. Over …
October 10 @ 9:00 am – 3:00 pmRHS Blacksmith Day
The Blacksmith Day (also known as the Blacksmith Day Hammer-In) is an annual fall event hosted by th…
October 10 @ 9:00 am – 4:00 pmPumpkin Party in the Park
Pumpkin Party in the Park, presented by Kiwanis of Greater Hartland, Village of Hartland, Hartland…
October 10 @ 4:00 pm – 8:00 pmHoly Hill Art Farm Market
Bring your family to the Holy Hill Art Farm Market! Unique Rustic Marketplace ~ Featuring Artists an…
October 11 @ 9:00 am – 4:00 pmDayspring Fall Harvest Fest
Dayspring Fall Harvest Fest is back in 2026! One of our favorite LAKE COUNTRY FALL FESTS is back! Jo…
October 11 @ 3:00 pm – 6:00 pmChrist Lutheran Fall Festival Pewaukee
Christ Lutheran Fall Festival Pewaukee 2026 Save the date for Fall Festival on Friday, October 16 fr…
October 16 @ 5:00 pm – 7:00 pmDowntown West Bend Fall Fest/ Trick or Treating
Friday October 16, 2026 5 p.m – 7 p.m. Little ghosts and goblins take over West Bend in th…
October 16 @ 5:00 pm – 7:00 pmBoo at the Zoo
Visit the Milwaukee County Zoo for a ghoulishly fun event and enjoy the leaves changing color, the c…
October 16 @ 5:30 pm – 9:00 pmJack-O-Lantern Jaunt & Halloween Haunt, Mukwonago
Jack-O-Lantern Jaunt & Halloween Haunt, Mukwonago is BACK in 2026!! The Jaunt/Haunt returns to F…
October 16 @ 6:00 pm – 9:30 pmBoo at the Zoo
Visit the Milwaukee County Zoo for a ghoulishly fun event and enjoy the leaves changing color, the c…
October 17 @ 9:30 am – 9:00 pmJack-O-Lantern Jaunt & Halloween Haunt, Mukwonago
Jack-O-Lantern Jaunt & Halloween Haunt, Mukwonago is BACK in 2026!! The Jaunt/Haunt returns to F…
October 17 @ 6:00 pm – 9:30 pmBoo at the Zoo
Visit the Milwaukee County Zoo for a ghoulishly fun event and enjoy the leaves changing color, the c…
October 23 @ 5:30 pm – 9:00 pmBoo at the Zoo
Visit the Milwaukee County Zoo for a ghoulishly fun event and enjoy the leaves changing color, the c…
October 24 @ 9:30 am – 9:00 pmHalloween in Delafield
The Delafield Area Chamber of Commerce invites the community down to see the amazing carvings by our…
October 24 @ 4:30 pm – 7:00 pmThe Fall Edit at Salt + Light Salon
The Fall Edit at Salt + Light Salon Join in for a cozy afternoon of shopping and beauty at Salt + Li…
October 25 @ 2:00 pm – 5:00 pmPumpkin Palooza Watertown
Pumpkin Palooza Watertown, Wisconsin is back in 2026! Come on down to Main Street on Saturday, Octob…
October 31 @ 12:00 pm – 3:00 pm
Frequently Asked Questions About Fall Festivals in Lake Country
When do fall festivals start in Lake Country?
Fall festivals in Lake Country and Waukesha County typically begin in late August or early September and continue through October, with many events taking place on weekends.
What are the best fall festivals for families in Waukesha County?
Lake Country and Waukesha County offer family-friendly fall festivals featuring carnival rides, live music, food, craft vendors, games, harvest activities and more. Browse the 2026 festival listings above to find events by date and community.
Are there free fall festivals in Lake Country?
Yes. Several local fall festivals and community celebrations offer free admission, although individual activities, food, rides or vendor purchases may have additional costs.
Where can I find fall festivals near Oconomowoc, Hartland, Delafield and Waukesha?
The guide above includes fall festivals throughout Lake Country and Waukesha County, organized chronologically so families can find events happening near them.
We love the Oconomowoc Fall Fest!
Pin this Guide:
Looking for more FALL Fun?
Check out our FALL FUN PAGE with guides to Haunted Houses, Pumpkin Farms, Fall festivals and more!
Want to be included in this Guide?
If you are hosting a Fall Festival and want to be included in our guide, please email us at erin@lakecountryfamilyfun(dot)com with your fall festival information. You can also email us via the contact form.
Related articles
Corn Maze Guide
SE Wisconsin has so many awesome Corn Mazes. Use this guide to find fall fun. Sponsored by Basses.
Fall Bucket List
Families love creating a fall bucket list every year. Check out ours!
All Things FALL
This is your go-to-guide for all things Fall in Lake Country, Waukesha County and SE Wisconsin. Sponsored by University Lake School.
Trick or Treat Guide
Covers the Trick or Treat times in Waukesha County and Metro Milwaukee. Sponsored by Bug & Goose Play Cafe in Elm Grove.
Apple Picking Farms
Great list of U-pick farms in SE Wisconsin. Locations listed by county. Sponsored by Peck & Bushel.
Haunted houses
Looking for a scare this season? Check out the list of Haunted Houses. Sponsored by American Ghost Walks.
