Oconomowoc Fall Fest 2026: Your Guide to a Weekend of Fall Fun

Fall is just around the corner in Lake Country, and one of Oconomowoc’s favorite seasonal events is returning to downtown for two days of live music, food, shopping and family-friendly activities.

Oconomowoc Fall Fest takes place Friday, September 11, and Saturday, September 12, 2026, centered around Downtown Oconomowoc and the Village Green.

Hosted by the Oconomowoc Area Chamber of Commerce, this year’s Fall Fest begins with a Friday evening of live music, food trucks and the Beer Garden before expanding into a full-day festival on Saturday with more than 100 artisan and merchant vendors, kids’ activities, food and three more live performances.

Whether you are planning to spend the entire day downtown or stop by for your favorite band, here is what you need to know before you go.

Friday, September 11: Concert Night

4:00 PM–9:00 PM | Village Green

Fall Fest gets underway Friday evening with food, drinks and live music at the Village Green.

The Beer Garden and food trucks will be open from 4:00–9:00 PM, and Rebel Grace takes the stage from 5:30–9:00 PM.

Friday Schedule

• Beer Garden & Food Trucks: 4:00–9:00 PM
• Rebel Grace: 5:30–9:00 PM

Friday is focused on the music, food trucks and Beer Garden. The vendor market and Kids’ Area take place Saturday.

Saturday, September 12: Fall Fest

9:00 AM–9:00 PM | Downtown Oconomowoc

Saturday brings the full Fall Fest experience to downtown Oconomowoc.

The artisan and merchant market runs from 9:00 AM–6:00 PM, with more than 100 vendors lining downtown for a full day of shopping.

Families can also visit the Kids’ Area from 10:00 AM–4:00 PM, while food trucks, the Beer Garden and live entertainment add to the festivities throughout the day.

Saturday Schedule

• Fall Fest: 9:00 AM–9:00 PM
• Artisan & Merchant Vendors: 9:00 AM–6:00 PM
• Kids’ Area: 10:00 AM–4:00 PM
• Food Trucks: 10:00 AM–9:00 PM
• Slim Rox: 1:00–3:00 PM
• Dirty Boogie: 3:30–5:30 PM
• Sons of Sconnie: 6:00–9:00 PM

Live Music at the Village Green

Music is a major part of this year’s Fall Fest, with four performances scheduled throughout the weekend.

Friday, September 11

• Rebel Grace | 5:30–9:00 PM

Saturday, September 12

• Slim Rox | 1:00–3:00 PM
• Dirty Boogie | 3:30–5:30 PM
• Sons of Sconnie | 6:00–9:00 PM

With music running into the evening both nights, visitors can make Fall Fest an afternoon outing, an evening downtown or a full Saturday of festivities.

Shopping, Food & Family Fun

Saturday is the day to plan for if shopping is at the top of your Fall Fest list. More than 100 artisan and merchant vendors are expected downtown, with the vendor market open from 9:00 AM–6:00 PM.

Food trucks will be set up along the Boardwalk, and the Village Green provides a central gathering place for the Beer Garden and live entertainment.

Families can also stop by the Kids’ Area from 10:00 AM–4:00 PM for additional activities during the festival.

Road Closure, Parking & Complimentary Trolley

With Fall Fest taking over the heart of downtown, visitors should plan ahead for Saturday parking.

Wisconsin Avenue from Cross Street to Main Street will be closed to vehicle traffic from 6:45 AM–10:00 PM on Saturday, September 12, allowing vendors and festival activities to fill the downtown corridor.

A complimentary trolley will run continuous loops to and from the Village Green from 9:00 AM–9:00 PM Saturday.

Parking and trolley pickup locations include:

• Oconomowoc Police Department – 630 E. Wisconsin Avenue
• Wisconsin Ave Metro Market – N48W36903 E. Wisconsin Avenue

Parking outside the immediate festival footprint and using the trolley can make getting downtown easier while Wisconsin Avenue is closed.

Make a Day of It in Downtown Oconomowoc

Fall Fest is also a great excuse to spend a little extra time exploring downtown Oconomowoc.

Between festival activities, take a walk through downtown, visit local shops and restaurants, or enjoy the lakefront scenery around Fowler Lake and Lac La Belle. With shopping, food and entertainment stretching from morning into the evening, there is plenty to fill an entire Saturday.

2026 Oconomowoc Fall Fest at a Glance

Friday, September 11
4:00–9:00 PM
Village Green
Food Trucks • Beer Garden • Live Music

Saturday, September 12
9:00 AM–9:00 PM
Downtown Oconomowoc & Village Green
100+ Vendors • Kids’ Area • Food Trucks • Beer Garden • Live Music

Saturday Road Closure
Wisconsin Avenue from Cross Street to Main Street
6:45 AM–10:00 PM

Complimentary Saturday Trolley
9:00 AM–9:00 PM

A Fall Weekend in the Heart of Oconomowoc

Community events like Fall Fest are one of the many ways residents and visitors get to experience what makes Oconomowoc such an enjoyable place to live. A vibrant downtown, lakefront setting, local businesses, community events and a variety of neighborhoods all contribute to the lifestyle that draws people to this part of Waukesha County.

At Berkshire Hathaway HomeServices Lake Country Realty, our office is right here in Oconomowoc, and our agents understand the communities, neighborhoods and real estate market throughout Lake Country.

Whether you are thinking about buying, selling or simply want to know what your home could be worth in today’s market, our local real estate professionals are here to help.

Enjoy Fall Fest, explore Oconomowoc, and when real estate is part of your plans, connect with Berkshire Hathaway HomeServices Lake Country Realty.

Fall Fest Friendly Reminder: We do our best to provide accurate, current information, but festival details can change. Please confirm schedules and event information with organizers before heading downtown.