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.

Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
August 29 @ 10:00 am – 6:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
August 30 @ 10:00 am – 6:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 4 @ 3:00 pm – 7:00 pm
Louie Fest
Mark your calendars for Louie Fest 2026. Louie’s third Epic Summer Party is taking over Dockhounds…
September 4 @ 5:30 pm – 11:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 5 @ 10:00 am – 6:00 pm
Louie Fest
Mark your calendars for Louie Fest 2026. Louie’s third Epic Summer Party is taking over Dockhounds…
September 5 @ 4:30 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 6 @ 10:00 am – 6:00 pm
Louie Fest
Mark your calendars for Louie Fest 2026. Louie’s third Epic Summer Party is taking over Dockhounds…
September 6 @ 4:30 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 7 @ 10:00 am – 5:00 pm
Louie Fest
Mark your calendars for Louie Fest 2026. Louie’s third Epic Summer Party is taking over Dockhounds…
September 7 @ 4:30 pm
St. Charles Fall Fest
September 11-13, 2026, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-d…
September 11 @ 12:00 pm – 11:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 11 @ 3:00 pm – 7:00 pm
Oconomowoc Fall Festival
Downtown Oconomowoc’s main street (Wisconsin Ave.) will close as vendors line both sides selli…
September 11 @ 4:00 pm – 9:00 pm
Fall Festival Pewaukee
Pewaukee Fall Festival & Movie in the Park 2026 Get ready for an evening of fall family fun at t…
September 11 @ 5:00 pm – 9:00 pm
Oconomowoc Fall Festival
Downtown Oconomowoc’s main street (Wisconsin Ave.) will close as vendors line both sides selli…
September 12 @ 9:00 am – 9:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 12 @ 10:00 am – 6:00 pm
Elegant Farmer Autumn Harvest Festival
Put the Elegant Farmer Autumn Harvest Festival on your fall schedule! Saturdays & Sundays only, …
September 12 @ 10:00 am – 5:00 pm
Delafield Brewhaus Oktoberfest
The Delafield Brewhaus is hosting an inside and outside party celebrating Oktoberfest! Put your danc…
September 12 @ 11:00 am – 8:00 pm
St. Charles Fall Fest
September 11-13, 2026, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-d…
September 12 @ 12:00 pm – 11:00 pm
Delafield Wine Walk and Brew Fest
Join the Delafield Area Chamber of Commerce in Downtown Delafield for their 7th Annual Wine Walk and…
September 12 @ 4:00 pm – 7:00 pm
Septemberfest
Kick-off fall with Septemberfest – a free event with RiverGlen Church. Bring the whole family,…
September 12 @ 4:00 pm – 7:00 pm
Septemberfest
Kick-off fall with Septemberfest – a free event with RiverGlen Church. Bring the whole family,…
September 13 @ 10:00 am – 1:00 pm
Apple and Sunflower Fest
Bring your family to Basse’s 7th annual Apple and Sunflower Fest! The sunflower and zinnias patch …
September 13 @ 10:00 am – 6:00 pm
Divine Redeemer Hartland Oktoberfest
Divine Redeemer Hartland Oktoberfest – Divine Redeemer is excited to host their 5th annual Okt…
September 13 @ 10:30 am – 2:30 pm
St. Charles Fall Fest
September 11-13, 2026, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-d…
September 13 @ 12:00 pm – 5:00 pm
North Prairie Harvest Festival
Bring your family to the North Prairie Harvest Festival on September 18, 19, and 20, 2026! This is …
September 18 @ 5:00 pm – 11:00 pm
North Prairie Harvest Festival
Bring your family to the North Prairie Harvest Festival on September 18, 19, and 20, 2026! This is …
September 19 @ 8:00 am – 11:00 pm
Retzer Nature Center Apple Harvest Festival
ENTER TO WIN A FREE CARLOAD PASS TO THE RETZER NATURE CENTER APPLE HARVEST FESTIVAL BELOW. Find mo…
September 19 @ 9:00 am – 4:00 pm
Cedarburg Wine and Harvest Festival
Come celebrate a sweet and savory weekend at the 52nd Annual Cedarburg Wine and Harvest Festival in …
September 19 @ 10:00 am – 6:00 pm
Mukwonago Fall Fest
Bring your family to the Mukwonago Fall Fest presented by the Mukwonago Area Chamber of Commerce and…
September 19 @ 10:00 am – 4:00 pm
North Lake Harvest Fest and Parade
Join us for the 33rd Annual North Lake Harvest Fest & Parade! . The festival is back and bigger …
September 19 @ 11:00 am – 9:30 pm
Three Pillars Fest
Mark your calendars for Three Pillars Fest. It will be 11:00 am to 3:00 pm on Saturday, September 19…
September 19 @ 11:00 am – 3:00 pm
Cedarburg Wine and Harvest Festival
Come celebrate a sweet and savory weekend at the 52nd Annual Cedarburg Wine and Harvest Festival in …
September 20 @ 10:00 am – 5:00 pm
North Prairie Harvest Festival
Bring your family to the North Prairie Harvest Festival on September 18, 19, and 20, 2026! This is …
September 20 @ 10:00 am – 5:00 pm
Annual Waukesha Oktoberfest
Join in for the 10th annual Waukesha Oktoberfest event for a taste of German in the heart of Waukesh…
September 25 @ 5:00 pm – 10:00 pm
Piala’s Nursery Fall Fest
Join Piala’s Nursery for their SIXTEENTH Annual Fall Fest! Piala’s Nursery Fall Fest wil…
September 26 @ 9:00 am – 4:00 pm
Makers Market of Stonewood Village
Makers Market of Stonewood Village is Saturday, September 26th, 2026! It’s a family friendly e…
September 26 @ 10:00 am – 4:00 pm
Annual Waukesha Oktoberfest
Join in for the 10th annual Waukesha Oktoberfest event for a taste of German in the heart of Waukesh…
September 26 @ 12:00 pm – 10:00 pm
Piala’s Nursery Fall Fest
Join Piala’s Nursery for their SIXTEENTH Annual Fall Fest! Piala’s Nursery Fall Fest wil…
September 27 @ 10:00 am – 3:00 pm
Golden Mast Oktoberfest
Welcome to the Golden Mast Oktoberfest in 2026! Come join in at Weissgerber’s Golden Mast Inn …
September 27 @ 1:00 pm – 6:00 pm
Abundant Life Church Fall Festival
Abundant Life Church Fall Festival 2026, starting at 3:00 pm! This year’s Fall Festival is fil…
October 3 @ 3:00 pm
Dayspring Fall Harvest Fest
Dayspring Fall Harvest Fest is back in 2026! One of our favorite LAKE COUNTRY FALL FESTS is back! Jo…
October 4 @ 3:00 pm – 6:00 pm
Pumpkin 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 pm
Dayspring 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 pm
Boo 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 pm
Boo 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 pm
Boo 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 pm
Boo 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 pm
Halloween 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 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!

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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.