Downtown Oconomowoc’s main street (Wisconsin Ave.) will close as vendors line both sides selling wares, food and more for the 14th annual Fall Festival. Free children’s games and an entertainment stage that will feature dance groups and live music will be on tap as well as a beer tent on Saturday, September 6.

NEW IN 2025: FRIDAY NIGHT!!

Kick things off with live music from local favorite from Rebel Grace, 6 pm – 9 pm.

Enjoy a crisp drink in the Beer Garden, and grab dinner from a variety of tasty food trucks.

Beer Garden and Food Trucks open from 4 – 9 pm.

It’s the perfect Friday night vibe for friends, families, and out-of-town guests!

NOTE: Wisconsin Avenue from Cross Street to Main Street will be closed from 6:45 a.m. to 10 p.m. Planning to attend? Park outside downtown and ride the trolley this year courtesy of Downtown Oconomowoc! Running from 11:00 am to 9:00 pm.

Shopping, Music, Dance, Food & Festivities!!
Live Music and Beer Tent

• BBQ to Bundt Cakes, Lobster Rolls to Doughnut Holes, it’s going to be hard to choose from all the yummy food.
• Over a dozen food vendors.
  • 18 Acres
  • Big Daddy’s BBQ
  • Bryants on the Round,
  • Chick-Fila-A
  • Dough Nation
  • Drifting Sips
  • Kona Ice
  • HB Slakter
  • Just Doughlightful
  • Quincy Waffle
  • Rocky Rocco’s
  • Say Cheese Curd
  • Scrima’s Pizza

Stroll through a vibrant market of craft and merchant vendors, discover handmade goods and unique finds, and treat the kids to fun activities in the Kids Area hosted by St. Paul’s Lutheran Church (10 AM–4 PM) on Saturday. The Beer Garden and food trucks will be serving all day—so come hungry and ready to relax!

2025 Fall Festival Entertainment

Musical Performances on Saturday

• Brett & The Dandys: 1PM–3PM
• Dirty Boogie: 3:30PM–5:30PM
• The Bar Downs: 6PM–9PM

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See our past fall fest fun HERE on Instagram.

Related:

Lake Country Fall Fest Guide

Find ALL THINGS FALL IN LAKE COUNTRY.