Area Fall Festivals: September Edition
Crisp air, crunchy leaves, and the smell of hot apple cider—there’s nothing quite like fall festivals across southern Wisconsin. From corn mazes in Janesville to pumpkin patches in Mount Horeb and cider tastings in New Glarus, every weekend feels like a celebration of all things autumn. You can cheer on the pumpkin chuckers in Sauk City, dance to live polka bands in Monroe, or pick the perfect gourd while munching on cinnamon-sugar donuts in Baraboo. With cozy flannels, hayrides under golden trees, and endless bratwursts, southern Wisconsin turns into a fall-lover’s playground - just don’t forget to grab a caramel apple (or three) for the road!
SEPTEMBER FESTIVAL GUIDE
3-7 Richland County Fair - Richland Center/fairgrounds
5 Art Infusion - Janesville/downtown river walk
5-6 Chilimania - Edgerton/downtown
5-6 Fall Fest 2025 - Oconomowoc/133 E Wisconsin Ave.
5-6 TosaFest - Wauwatosa/downtown
5-7 Dairy Days - Platteville/Legion Park
5-7 Heritage Days - Beloit/citywide
5-7 Wild West Days – Mazomanie/Lions Park
6 Oktoberfest – Madison/Essen Haus
6 Pick-A-Peck Apple Fest – Fort Atkinson/Warm Belly Farm (W8974 Hwy C)
6 Thirsty Troll Fest - Mt. Horeb/Tyrol Basin
6 Watermelon Festival - Pardeeville/Chandler Park
6 Wisconsin State Chili Cookoff - Green Lake/Deacon Mills Park
11-14 Wauktoberfest – Waunakee/Endres Manufacturing Co.
12-14 Gemuetlichkeit Days – Jefferson/Fair Park
12-14 Wo-Zha-Wa Days Fall Festival - Wisconsin Dells/downtown
13 Street Festival - Monroe/downtown
13 Pepper Festival - Beaver Dam/Park Village Shopping Center
18 Madison Night Market - Madison/State St. & Capitol Square
19-20 Oktoberfest - Waukesha/Frame Park
20 Baraboo Oktoberfest – Baraboo/Circus World
20 Brew-B-Que 2025 – Lodi/downtown
20 Fall Festival - Beloit/downtown
20-21 Driftless Area Art Festival - Soldiers Grove/Beauford T. Anderson Park
20-21 Willy Street Fair - Madison/800-1000 blocks of Williamson St.
25 Sip & Stroll: Beer & Cider Edition - Middleton/downtown
25-28 Oktoberfest - New Glarus/downtown
25-28 Art of Cheese Festival - Madison/Capitol Square
26 Fall Fest - Verona/Hometown USA Festival Park
26-28 Apple Festival - Gays Mills/downtown
26-28 Cornish Festival - Mineral Point/Opera House
26-28 Cranberry Festival - Warrens/402 Pine Street
27 42nd Chili Cookoff - Monona/Ahuska Park
27 Lions Chili Fest – Deerfield/Fireman’s Park
27 True North Music and Food Festival – Madison/Duck Pond
27 Wagons and Wine – Baraboo/Circus World
27-28 Golden Days Harvest Festival - Green Lake/downtown
30-10/3 World Dairy Expo - Madison/Alliant Energy Center