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Last updated: November 11, 2024

Discover holiday wonders in Waukesha with our detailed event listings. Whether you're intimately familiar with Waukesha or just getting acquainted, this guide maximizes your seasonal joy.

Popular Events: Experience the vibrant spirit of the season with a mesmerizing performance by the Trans-Siberian Orchestra, where rock elements meet classical music in a spectacular holiday concert. Features such as stunning visual effects and powerful musical arrangements elevate this event. And the timeless performance of the Milwaukee Ballet - The Nutcracker is something you definitely don't want to miss, showcasing captivating choreography and enchanting music. See more details on these and other fun events and activities below!

Contact information and details below.

Waukesha Holiday Light Displays

What to Expect:

Drive-through holiday lights display with animated figures and holiday scenes.

Description:

Country Christmas is a spectacular drive-through holiday lights event featuring over a million lights displayed on 40 wooded acres. The event includes a trip through the Country Christmas Trail, entrance to Christmas Village, and Streets of Bethlehem. Each year, the Ingleside Hotel is transformed into a winter wonderland.

Where: Waukesha | More Info: Country Christmas: Christmas Lights Display

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What to Expect:

Bike-friendly holiday light display with animated figures and festive scenes.

Description:

Guests can bike through the Country Christmas trail, featuring over a million holiday lights, on special nights when the drive-through traffic is closed.

Where: Waukesha | More Info: Bikes and Lights

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What to Expect:

Unique holiday light display with interactive village and nativity scene.

Description:

Country Christmas at The Ingleside Hotel features over a million holiday lights displayed on 40 wooded acres. Guests can drive through the trail, visit Christmas Village for hot chocolate and animated scenes, and stroll through the Streets of Bethlehem. The event includes various special nights with discounts and activities.

Where: Waukesha | More Info: Christmas Lights Specials

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Waukesha Holiday Shows and Entertainment

What to Expect:

Immersive theatrical experience with real train ride to the North Pole.

Description:

The Polar Express Train Ride at the National Railroad Museum is a re-creation of the classic children's story, featuring a dramatic reading of the book, a hot chocolate dance, and a ride on a real train to the North Pole. Guests interact with characters from the story, encounter a hobo, view the Northern Lights, and see polar bears in the Arctic Circle. Santa visits some passengers onboard the train, and those who did not visit him on the train have time to see him before he heads around the world on Christmas Eve.

Where: Waukesha | More Info: The Polar Express

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What to Expect:

Community-driven celebration with historical streets lined with eager spectators.

Description:

The Waukesha Christmas Parade is a cherished community event featuring colorful floats, marching bands, and Santa Claus, bringing warmth and togetherness to Downtown Waukesha.

Where: Waukesha | More Info: Waukesha Christmas Parade

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What to Expect:

Grammy-winning holiday concert with multimedia effects.

Description:

Mannheim Steamroller presents a holiday tradition featuring Christmas classics in the distinctive Mannheim sound, accompanied by dazzling multimedia effects in an intimate setting.

Where: Milwaukee | More Info: Mannheim Steamroller

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What to Expect:

Live performance of a holiday rock opera with pyrotechnics and lasers.

Description:

Trans-Siberian Orchestra presents The Ghosts of Christmas Eve, a holiday rock opera featuring a runaway who breaks into an abandoned vaudeville theater on Christmas Eve, with a story that turns her life around through the ghosts and spirits of the building's past. The show includes a rocking, blazing, and laser-lit second set with TSO's greatest hits and fan-favorites.

Where: Milwaukee | More Info: Trans-Siberian Orchestra: The Ghosts of Christmas Eve

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What to Expect:

Elaborate sets and costumes in a classic ballet performance.

Description:

Milwaukee Ballet's The Nutcracker is a timeless holiday tradition featuring Tchaikovsky's beloved score performed live by the Milwaukee Ballet Orchestra, accompanied by the full Company of dancers and students from Milwaukee Ballet School & Academy.

Where: Milwaukee | More Info: Milwaukee Ballet - The Nutcracker

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What to Expect:

Period costumes and special effects bring Dickens' classic to life.

Description:

A Christmas Carol, directed by Mark Clements, brings Charles Dickens' timeless tale to life at the Pabst Theater. Ebenezer Scrooge, played by Matt Daniels, is visited by the ghosts of Christmas Past, Present, and Future, leading him to a transformative Christmas Eve. With enchanting music, dance, costumes, and special effects, this production is a holiday tradition filled with love, hope, and redemption.

Where: Milwaukee | More Info: A Christmas Carol

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What to Expect:

Exclusive Q&A with Macaulay Culkin about his iconic role in Home Alone.

Description:

Join Macaulay Culkin for a special screening of the timeless classic, Home Alone, followed by an exclusive moderated interview and audience Q&A. Fans will hear Culkin discuss his on-set experiences, favorite memories from filming, and why the movie remains a beloved holiday classic.

Where: Milwaukee | More Info: Home Alone Tour With Macauley Culkin

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What to Expect:

Exclusive Q&A with Macaulay Culkin about his experiences filming "Home Alone."

Description:

Join Macaulay Culkin for a special screening of the timeless classic "Home Alone," followed by an exclusive moderated interview and audience Q&A. Relive iconic scenes and hear behind-the-scenes stories from the beloved holiday film.

Where: Milwaukee | More Info: A Nostalgic Night with Macaulay Culkin

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What to Expect:

World-class acrobatics and re-invented holiday classics.

Description:

Twas the Night Before... is Cirque du Soleil's first holiday show, inspired by the classic poem "A Visit from Saint Nicholas" by Clement Clarke Moore. The show features a jaded young girl who rediscovers the magic of the holidays through thrilling acrobatics, lovable characters, and re-invented holiday classics.

Where: Milwaukee | More Info: Holiday & Christmas Shows at Pabst Theater

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What to Expect:

Cirque du Soleil's first holiday show with thrilling acrobatics and re-invented holiday classics.

Description:

Twas the Night Before... by Cirque du Soleil is a holiday show inspired by the classic poem "A Visit from Saint Nicholas." It features thrilling acrobatics, lovable characters, and a soundtrack of re-invented holiday classics. The show is directed by Cirque du Soleil Senior Artistic Director James Hadley, a 25-year veteran of circus productions and live theater.

Where: Milwaukee | More Info: Holiday & Christmas Shows at Miller High Life Theatre

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What to Expect:

Exclusive VIP packages with best-in-house seats and intimate performances.

Description:

Pentatonix, a three-time GRAMMY Award-winning and Daytime EMMY Award-nominated quintet, will perform at Fiserv Forum on December 17, 2024, celebrating the holiday season with their biggest Christmas tour yet. The event includes unique VIP options and exclusive benefits.

Where: Milwaukee | More Info: Holiday & Christmas Shows at Fiserv Forum

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Waukesha Other Holiday Activities

What to Expect:

Spooky bar crawl with exclusive drink specials and a $1,000 costume contest.

Description:

Join thousands of spooky crawlers for a spooktacular night of bar-hopping in Milwaukee. Enjoy 2-3 drinks or shots included, no cover at all bars, and participate in a $1,000 national costume contest. Explore some of the best bars in Milwaukee and enjoy an electric atmosphere that only Halloween can provide.

Where: Milwaukee | More Info: The Official Halloween Bar Crawl - Milwaukee

Event Organizer?

What to Expect:

DIY pallet pumpkin workshop with pre-cut wood and painting materials.

Description:

Create your own unique pallet-style pumpkin at Fisk Avenue DIY Studio, available in small and large sizes. This workshop provides pre-cut wood pieces, mounting materials, paints, and stains. You can either mount your pumpkin on the wall or place it outside. The event is suitable for individuals and pairs, with individuals under 18 allowed if accompanied by an adult.

Where: Waukesha | More Info: Pumpkin Painting Party

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