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September 10, 2025 30 mins

Looking for some awesome things to do in and around Milwaukee this fall? We've got you covered. Richie sits down with Claire from VISIT Milwaukee to cover: 

Festivals 

  • Wine & Harvest Fest - Cedarburg, Sep 20-21
  • Oktoberfests
    • MKE at Summerfest Grounds for the first time 
    • Germantown, Sept 27-28
    • Cedarburg, Oct 4-5
    • Bavarian Brew House 
    • Burlington, Oct 4
    • Lake Geneva, Oct 11-12
  • Harvest Fair at Wisconsin State Fair Park - Sept 26-28
  • 150th anniversary of the Milwaukee Fire Dept 



Events 

  • Milwaukee Uncut/CLRC 
  • New Berlin: Ultimate Fall Craft & Vendor Fair at New Berlin Ale House, Sept. 28
  • Holy Hill Arts & Crafts Fair - Hubertus, Sep 20
  • Sunday, September 21, Football Tailgate at Davidson Park
  • Southside dining week September 27 - October 4 
    • Zocalo Food Truck Park Sept 29 - 12pm - 3pm 
  • Oak Creek: Fall Festival at Drexel Town Square, Oct. 25
  • Bay View Bash - Sep 20
  • Milwaukee Flavor Live Cooking classes at Milwaukee Public Market
  • Milwaukee Theater Week 



Places/gems 

  • Fall Brewery Guide 
  • Basses Farms (pumpkin fest Sept 20 - Oct 31)
  • Pack and Bushel 
  • The Elegant Farmer
  • Potawatomi’s Sportsbook since it’s officially football season?
  • Vm cookbook this fall! Perfect for gifting. 



New Openings

  • Walker’s Point 
    • Mobcraft 
    • Banderas 
  • Your office 
  • Cassis - French Bistro (Water St.) - same owner as Birch (James-Beard nominated Kyle Knall)
  • Associated Bank Theater Center 
  • Tosa Troll 



Little Road Trips 

  • Football: Badgers/Packers 
  • Holy Hill 
  • Hikes
    • Paradise Springs in Eagle, WI + East Troy + Deusterbecks + Eagle Park 
    • Hikes 
    • Post card cabins 
  • House on the Rock - Spring Green, WI
  • The Little Farmer - Malone, WI
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