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What to do in Oconomowoc

Between Monday, November 17, 2025 and Friday, January 16, 2026

Greenway Supernova
Dec 11An event at the Lafitte Greenway, featuring various activities, potentially including music.
Trivia Night at The Village
Dec 15Test your knowledge at this local trivia event.
Trivia Night at Monk's Bar & Grill
Dec 16Enjoy a night of trivia with friends.
2025 CBG & NAIOP Holiday Meeting and Party
Dec 16A holiday gathering for the Commercial Brokers Group (CBG) and NAIOP.
MYC's Winter Concert Series, “In Other Words”
Dec 17A winter concert performance by MYC.
Middleton Community Orchestra Holiday Concert
Dec 17Enjoy a festive holiday concert by the Middleton Community Orchestra.
Trivia Night at Monk's Bar & Grill
Dec 18Enjoy another night of trivia with friends.
MYC's Winter Concert Series, “In Other Words”
Dec 18Another performance in the MYC winter concert series.
Wallflower Vision Board
Dec 9A creative workshop focused on vision boarding.
Holiday Business Social Hour
Dec 9Enjoy appetizers, refreshments, and holiday cheer with new and old friends.
Preschool Storytime
Dec 9Storytime tailored for preschoolers.
Reindeer Party
Dec 10A festive party event, likely geared towards children.
Asi Respiro: Bilingual Storytime & Breathing Stations with Local Author
Dec 10Enjoy a bilingual storytime session and breathing exercises with a local author.
Holiday Art Market at FCI
Dec 13Explore and shop at a vibrant art market.
Chunky Blanket Workshop
Dec 13Learn to make a chunky blanket.
Middleton High School Choir
Dec 11A musical performance by the Middleton High School Choir.
Poetry & Pi(e) 2025!
Dec 13An inspiring evening of poetry featuring Wisconsin's new Poet Laureate.
Holiday Floral Show at Mitchell Park Domes
Nov 22The Show Dome transforms with unique, themed floral shows.
Christmas at the Pabst Mansion
Nov 20Holiday decorations and tours at the historic Pabst Mansion.
Jackie Kashian
Dec 29Comedy performance by Jackie Kashian.
Kwik Trip Holiday Face-Off
Dec 28College hockey tournament.
Jackie Kashian
Dec 28Comedy performance by Jackie Kashian.
Twilight Tours at Pabst Mansion
Dec 27Evening tours of the historic Pabst Mansion.
Trans-Siberian Orchestra
Dec 27Highly anticipated 2025 Winter Tour performance with shows at 3 p.m. and 7:30 p.m.
Play Date with Art: Winter
Dec 27An art-themed play date for kids.
Milwaukee Holiday Lights Festival
Nov 20A festival of festive light displays throughout downtown Milwaukee.
Julia Danielle
Dec 27Enjoy a live music performance by Julia Danielle at the Council Oak venue.
Christmas at Pabst Mansion / Twilight Tours
Nov 28A self-guided evening tour through lavishly decorated rooms with twinkling lights and live holiday music.
USM's Winter Day Camp
Dec 22Day camp for children in PK through 8th grade with winter-themed activities.
Shine On Madison
Dec 27Experience the festive light display on State Street, illuminating downtown Madison for the holiday season.
Madison TubaChristmas
Dec 28Join Madison's rendition of a nationwide tradition where tuba and euphonium players perform festive tunes.
Nate Craig
Dec 28Enjoy an evening of stand-up comedy with Nate Craig at the Majestic Theatre.
Holiday Fantasy in Lights
Dec 22A beloved drive-through holiday light display in Madison.
Shine On Madison: Holiday Tree Lighting & Capitol Square Décor
Dec 22Downtown Madison is illuminated with sparkling lights and festive decorations on Capitol Square for the holiday season.
The Harlem Globetrotters 100 Year Tour
Dec 27Catch the world-famous Harlem Globetrotters as they bring their spectacular 100 Year Tour to Madison.
A Christmas Carol
Nov 21Essential to the holiday season in Denver, this classic tale of Ebenezer Scrooge's transformation is brought to life on stage.