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Posted on: September 7, 2022

Fall Loving in Oconomowoc

Oconomowoc Halloween icon

Here's your Fall lineup of fun in Oconomowoc!

Fall FestNo doubt this event is an iconic annual happening ushering in all things fall. Crafts,music, food, darker beers! So many things we have to close Wisconsin Avenue downtown fit it all!

Check out the Downtown Oconomowoc Business District's Fall Fest celebration from 10am-9pm.

Oconomowoc loves a good parade and we love our hometown sports! Plan to attend all the fun starting with the parade through downtown at 5 p.m. Friday!

  • Oktoberfest is a Must! - Grab a Beer Sept. 23-24 - The Oconomowoc German Christmas Market is starting the celebration early. Come support this event and grab a seasonal beer and some food at Village Green during this beer garden celebrating the onset of Oktoberfest season.

  • National Night Out - Hang out with your local Police Department, Fire Department and many other community organizations committed to sharing info on a safe and healthy community. There will be giveaways, activities and fun things to see! Oconomowoc's National Night Out is 4-7pm Monday, Oct. 10. It's a school day off, so plan this as part of your fun!

  • Fall Fashion - Oconomowoc Woman's Club Style Show Oct. 12 -
    Grab the girls and enjoy a luncheon and style show at the Golden Mast to support this local service organization.

  • Broomsticks, Hats and Shopping - Downtown's Witches Night Out is Oct. 20 - Bad witch, good witch, all of the witches get together and enjoy this fun night out of shopping and dining downtown.
    Widows Weekend Downtown Oconomowoc
  • All Hallow's Eve in Oconomowoc! - Lions Halloween Parade and Trick or Treat Oct. 29 - Dress up and have some fun. Start downtown with business Trick or Treat from 2-4pm; grab some free food thanks to the Oconomowoc Lions Club and enjoy the parade they organize at 5pm. Then gather your people and find your favorite neighborhoods to Trick or Treat from 6-8pm.

  • Guy Gone Hunting? Downtown has Widow's Weekend Planned Nov. 18 -How about a Widow's Weekend Wine Walk. Shop, sip, stroll downtown with your friends!




  • Catch a Show at the OAC, Check out the Fall Lineup -Wisconsin Philharmonic Halloween show? Momma Mia!? and more. Check out what's coming to the stage at the Oconomowoc Arts Center.

Still More in September!


We'd be remiss if we didn't mention these September highlights!

  • 9/11 Remembrance

This annual commemorative event begins with the playing of "Taps" at the Village Green downtown at the time of the attacks in the morning. The day concludes with a concert at the City Beach band shell. This year features vocalist Bob Koslowski, an Air Force veteran and vocalist known for singing at the Brewer's games. 

Buddy's Beach Bungalow says, "You gotta regatta!" That is build your best version of a cardboard boat and let's see if it's sea worthy! Join the fun Sept. 18! The event also features a free concert by This Side Up. . 

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