Oconomowoc Fall Festival 2025: Your Family Guide

Downtown Oconomowoc is about to transform into a hub of autumn celebration for the 14th Annual Fall Festival, and this year brings a brand-new twist: a Friday night kickoff! From shopping and food trucks to live music and family fun, this festival is one of the season’s must-attend events.

Friday Night Kickoff – New for 2025

Start the weekend early on Friday, September 5, with a perfect small-town Friday night vibe.

• Live Music: Rebel Grace, 6–9 p.m.

• Beer Garden & Food Trucks: Open from 4–9 p.m. with dinner, drinks, and sweet treats to keep everyone fueled.

• Family-Friendly Fun: Stroll downtown, enjoy the crisp evening air, and soak in the festive atmosphere.

Note: Wisconsin Avenue (Cross St. to Main St.) will be closed to traffic 6:45 a.m.–10 p.m. Trolley service will not run Friday.

Saturday – The Main Event

The heart of the festival unfolds on Saturday, September 6 with a full day of entertainment and activities.

Food & Vendors

From BBQ to bundt cakes, lobster rolls to doughnut holes, there’s something for every craving. More than a dozen vendors will be on-site, including:

• Big Daddy’s BBQ

• Chick-Fil-A

• Dough Nation

• Kona Ice

• Quincy Waffle

• Say Cheese Curd

• Scrima’s Pizza
  …and many more!

Plus, browse unique craft and merchant booths lining Wisconsin Avenue for handmade goods and one-of-a-kind finds.

Kids’ Zone

The Kids Area, hosted by St. Paul’s Lutheran Church, will be open from 10 a.m.–4 p.m. with free games and activities.

Live Music Lineup – Saturday

The festival’s entertainment stage will keep the music going all day:

• Brett & The Dandys: 1–3 p.m.

• Dirty Boogie: 3:30–5:30 p.m.

• The Bar Downs: 6–9 p.m.

Beer Garden

Grab a crisp fall beverage, kick back, and enjoy the tunes. The Beer Garden will be open all day alongside the food trucks.

Getting There & Parking

Downtown Oconomowoc gets busy during the festival, so plan ahead:

• Road Closures: Wisconsin Avenue will be closed Saturday from Cross Street to Main Street.

• Complimentary Trolley Service: Runs continuous loops 9 a.m.–9 p.m. Saturday to and from the Village Green.

Pick-up locations:

• Our Savior’s Lutheran Church (145 E Lisbon Rd)

• Oconomowoc Police Department (630 E Wisconsin Ave)

• Wisconsin Ave Metro Market (N48W36903 E Wisconsin Ave)

Festival Snapshot

• When: Friday, Sept. 5 (4–9 p.m.) & Saturday, Sept. 6 (all day)

• Where: Downtown Oconomowoc (Wisconsin Ave.)

• Cost: Free admission

From foodies and music lovers to families and out-of-town guests, the Oconomowoc Fall Festival offers something for everyone. Whether you’re hopping on the trolley, trying your first lobster roll, or dancing under the stars, this is small-town Wisconsin at its best.