Fall Fest Pumpkin Laikin Fall Festival Lake Country

Lake Country Family Fun Fall Fest Guide

🍂 Discover the Best Fall Festivals in Lake Country & Waukesha County 🍎

Fall in Wisconsin is magical—cool crisp air, vibrant leaves, apple orchards, pumpkin patches, and family traditions that make this season unforgettable. If you’re searching for the best fall festivals, harvest events, and family-friendly activities in Lake Country and Waukesha County, you’ve come to the right place!

From pumpkin farms and corn mazes to Oktoberfest celebrations and craft fairs, we’ve rounded up everything you need to plan your perfect autumn weekend. Whether you’re sipping hot cider, picking apples, or enjoying live music, this Fall Festival Guide will help you make the most of the season.

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 Brian

 
6th Degree Properties Lake Country Brian

 

Fall Festivals in 2025

  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    August 30 @ 10:00 am6:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    August 31 @ 10:00 am6:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 1 @ 10:00 am5:00 pm
  • St. Charles Fall Fest

    Open House St. Charles Friday Morning Mom Group Lake Country Family Fun Local Preschool Guide

    September 5-7 2025, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-day …

    September 5 @ 12:00 pm11:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 5 @ 3:00 pm7:00 pm
  • Oconomowoc Fall Festival

    Oconomowoc Fall Festival Lake Country Family Fun

    Downtown Oconomowoc’s main street (Wisconsin Ave.) will close as vendors line both sides selli…

    September 5 @ 4:00 pm9:00 pm
  • St. Luke Fall Festival

    St. Luke Fall Festival is located at 18000 W. Greenfield in Brookfield and will be held on Friday, S…

    September 5 @ 4:00 pm11:00 pm
  • Lightning Night Fall Fest at LCL High School

    Lightning Night Fall Fest at LCL High School is coming up in September 2025! Enjoy an evening of fun…

    September 5 @ 5:00 pm9:00 pm
  • Oconomowoc Fall Festival

    Oconomowoc Fall Festival Lake Country Family Fun

    Downtown Oconomowoc’s main street (Wisconsin Ave.) will close as vendors line both sides selli…

    September 6 @ 9:00 am9:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 6 @ 10:00 am6:00 pm
  • St. Charles Fall Fest

    Open House St. Charles Friday Morning Mom Group Lake Country Family Fun Local Preschool Guide

    September 5-7 2025, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-day …

    September 6 @ 12:00 pm11:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 7 @ 10:00 am6:00 pm
  • St. Charles Fall Fest

    Open House St. Charles Friday Morning Mom Group Lake Country Family Fun Local Preschool Guide

    September 5-7 2025, St. Charles Fall Fest in Hartland will host Lake Country’s favorite 3-day …

    September 7 @ 12:00 pm6:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 12 @ 3:00 pm7:00 pm
  • North Prairie Harvest Festival

    North Prairie Harvest Festival

    Bring your family to the North Prairie Harvest Festival on September 12, 13, and 14, 2025! This is …

    September 12 @ 5:00 pm11:00 pm
  • North Prairie Harvest Festival

    North Prairie Harvest Festival

    Bring your family to the North Prairie Harvest Festival on September 12, 13, and 14, 2025! This is …

    September 13 @ 8:00 am11:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 13 @ 10:00 am6:00 pm
  • Delafield Brewhaus Oktoberfest

    The Delafield Brewhaus is hosting an inside and outside party celebrating Oktoberfest! Put your danc…

    September 13 @ 11:00 am11:00 pm
  • Delafield Wine Walk and Brew Fest

    Delafield wine walk and brewfest

    Join the Delafield Area Chamber of Commerce in Downtown Delafield for their 6th Annual Wine Walk and…

    September 13 @ 4:00 pm7:00 pm
  • Septemberfest

    Kick-off fall with Septemberfest – a free event with RiverGlen Church. Bring the whole family,…

    September 13 @ 4:00 pm7:00 pm
  • Septemberfest

    Kick-off fall with Septemberfest – a free event with RiverGlen Church. Bring the whole family,…

    September 14 @ 10:00 am1:00 pm
  • North Prairie Harvest Festival

    North Prairie Harvest Festival

    Bring your family to the North Prairie Harvest Festival on September 12, 13, and 14, 2025! This is …

    September 14 @ 10:00 am5:00 pm
  • Apple and Sunflower Fest

    Basses Taste of Country

    6th annual Apple and Sunflower Fest is coming soon at Basse’s Taste of Country! The sunflower …

    September 14 @ 10:00 am6:00 pm
  • Annual Waukesha Oktoberfest

    Join in for the 9th annual Waukesha Oktoberfest event for a taste of German in the heart of Waukesha…

    September 19 @ 5:00 pm10:00 pm
  • Louie Fest

    Mark your calendars for Louie Fest 2025. Louie’s second Epic Summer Party is taking over WBC Park …

    September 19 @ 5:30 pm11:00 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 20 @ 9:00 am4:00 pm
  • Louie Fest

    Mark your calendars for Louie Fest 2025. Louie’s second Epic Summer Party is taking over WBC Park …

    September 20 @ 9:00 am11:00 pm
  • North Lake Harvest Fest and Parade

    North Lake Harvest Fest & Parade

    Join us for the 32nd Annual North Lake Harvest Fest & Parade! . The festival is back and bigger …

    September 20 @ 10:00 am10:00 pm
  • Abundant Life Church Fall Festival

    Abundant Life Church Fall Festival 2025 from 10am-1pm This year’s Fall Festival is filled with…

    September 20 @ 10:00 am1:00 pm
  • Mukwonago Fall Fest

    Mukwonago

    Bring your family to the Mukwonago Fall Fest presented by the Mukwonago Area Chamber of Commerce and…

    September 20 @ 10:00 am4:00 pm
  • Cedarburg Wine and Harvest Festival

    Cedarburg Wine and Harvest Festival

    Come celebrate a sweet and savory weekend at the 51st Annual Cedarburg Wine and Harvest Festival in …

    September 20 @ 10:00 am6:00 pm
  • Three Pillars Fest

    Mark your calendars for Three Pillars Fest. It will be 11:00 am to 3:00 pm on Saturday, September 20…

    September 20 @ 11:00 am3:00 pm
  • Annual Waukesha Oktoberfest

    Join in for the 9th annual Waukesha Oktoberfest event for a taste of German in the heart of Waukesha…

    September 20 @ 12:00 pm10:00 pm
  • Cedarburg Wine and Harvest Festival

    Cedarburg Wine and Harvest Festival

    Come celebrate a sweet and savory weekend at the 51st Annual Cedarburg Wine and Harvest Festival in …

    September 21 @ 10:00 am5:00 pm
  • Louie Fest

    Mark your calendars for Louie Fest 2025. Louie’s second Epic Summer Party is taking over WBC Park …

    September 21 @ 12:00 pm3:00 pm
  • Piala’s Nursery Fall Fest

    Piala's Nursery Fall Fest

    Join Piala’s Nursery for their FIFTEENTH Annual Fall Fest! Piala’s Nursery Fall Fest wil…

    September 27 @ 9:00 am4:00 pm
  • Fall Harvest Festival – Multi Farm Event

    Fall Harvest Festival – Multi Farm Event Fall is coming! Glacier Rock Farms is kicking off the…

    September 27 @ 9:00 am4:00 pm
  • Popesfest at Pius XI Catholic High School

    Popesfest at Pius XI Catholic High School Pius XI Catholic High School is excited to host its 4th an…

    September 27 @ 12:00 pm7:00 pm
  • Piala’s Nursery Fall Fest

    Piala's Nursery Fall Fest

    Join Piala’s Nursery for their FIFTEENTH Annual Fall Fest! Piala’s Nursery Fall Fest wil…

    September 28 @ 10:00 am3:00 pm
  • Dayspring Fall Harvest Fest

    Dayspring Fall Harvest Fest is back in 2025! One of our favorite LAKE COUNTRY FALL FESTS is back! Jo…

    October 5 @ 3:00 pm6:00 pm
  • Our Lady of Lourdes Oktoberfest

    Join Our Lady of Lourdes Catholic Church on October 10-12, 2025 to celebrate the gifts of their vibr…

    October 10 @ 4:00 pm9:00 pm
  • Our Lady of Lourdes Oktoberfest

    Join Our Lady of Lourdes Catholic Church on October 10-12, 2025 to celebrate the gifts of their vibr…

    October 11 @ 11:00 am9:30 pm
  • Pumpkin Party in the Park

    Pumpkin Party in the Park: On behalf of the Kiwanis Club of Greater Hartland, the Hartland Public Li…

    October 11 @ 4:00 pm8:00 pm
  • Our Lady of Lourdes Oktoberfest

    Join Our Lady of Lourdes Catholic Church on October 10-12, 2025 to celebrate the gifts of their vibr…

    October 12 @ 9:00 am1:00 pm
  • Dayspring Fall Harvest Fest

    Dayspring Fall Harvest Fest is back in 2025! One of our favorite LAKE COUNTRY FALL FESTS is back! Jo…

    October 12 @ 3:00 pm6:00 pm
  • Pewaukee Halloween Fun Fest

    Halloween Fun Fest

    Join one of our favorite annual events in Pewaukee: Halloween Fun Fest! It’s back for 2025! Hallow…

    October 18 @ 12:00 pm1:45 pm
  • Halloween in Delafield

    Halloween in Delafield

    The Delafield Area Chamber of Commerce invites the community down to see the amazing carvings by our…

    October 18 @ 5:00 pm8:00 pm
  • Menomonee Falls Public Library Fall Family Fest

    Menomonee Falls Public Library Fall Family Fest Celebrate the fall season at the library, with a mor…

    October 25 @ 10:00 am11:30 am

We love the Oconomowoc Fall Fest!


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Fall Fest Guide Lake Country

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.

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