September festivals and fairs in Madison, WI

Grab a sweater + a pumpkin spice latte, here’s the scoop on this month’s fall season festivities.

A live acoustic performance during the Monroe Street Festival

Catch a show at the corner of Monroe Street and West Lawn Avenue

Photo by @monroestreetmadison

Summer may be coming to a close but the fall festival + fair circuit in the 608 is just kicking off. From hayrides and pumpkin spice lattes to beer fests and block parties, check out these upcoming September events.

Willy Street Fair | Sat., Sept. 17 + Sun., Sept. 18
Presented by Dane Arts + produced by the Wil-Mar Neighborhood Center and Common Wealth Development, this outdoor music + food festival is taking over the 800-1000 blocks. Jam out across four stages, shop from boutique retailers, and feast on local bites.

New Glarus Oktoberfest | Thurs., Sept. 22-Sun., Sept. 25
Celebrate Oktoberfest in America’s “Little Switzerland.” Immerse yourself in tradition with horse drawn wagon rides, chainsaw carving, and tapping the wooden keg during the four day festival. Oh, and of course — sip on a variety of local brews.

Monroe Street Festival | Sat., Sept. 24
Make your way to the 1700-1900 + 2500-2600 blocks of Monroe Street for the 44th annual festival. The Monroe Street Merchants Association presents live music sets, free pilates classes, and grab-and-go snacks from your favorite local eateries.

Capital Brewery Oktoberfest | Sat., Sept. 24
Spend the day at Capital’s biergarten sipping on the holiday’s namesake at brewery’s 2nd annual celebration. In addition to their classic Oktoberfest brew, try Autumnal Fire (a limited release Doppelbock Lager). Plus, catch live sets from a German polka party band + a Madison-based 7-piece country show band.

Verona Fall Fest | Fri., Sept. 30
Ring in the new season at Hometown USA Festival Park. Free hay rides, live music, fall-themed games, and an evening screening of “The Goonies” all make for family-friendly night out. Pro tip: The giant bonfire is a spectacle you won’t want to miss.