Here are our top five picks for kids and families happening around Milwaukee this weekend. You can find this on the Weekend Guide page, too. (It's updated every Wednesday.)

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Featured Event: “Annie” At Skylight Music Theatre

November 17, 2017 through December 27, 2017

Skylight Music Theatre (158 N Broadway, Milwaukee, WI 53202)​

Spend the holidays with Annie at Skylight Music Theatre! Bring the whole family to this heartwarming Broadway musical that has won seven Tony Awards and captivated audiences with a beloved story and an inspiring score, featuring the unforgettable hit song, “Tomorrow.” Skylight Music Theatre is located in the heart of the Historic Third Ward, just steps away from Christmas in the Ward, local boutiques, dining, the Milwaukee Public Market and more!

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#1. Gingerbread House Display (Free!)

Milwaukee Public Market

400 N. Water St., Milwaukee, WI 53202

(414) 336-1111

December 1st - 13th

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Stop by the second floor of the Milwaukee Public Market from December 1st to December 13th and marvel at over 40 festive and intricate ginger bread houses created by MATC students. The public is encouraged to view and bid on the lovely houses. You can vote for your favorite, too! Proceeds from silent auctions for each house will be used to offer scholarships to students in baking and pastry arts programs through the MATC Foundation, Inc.

#2. Canadian Pacific Holiday Train comes to Milwaukee (Free!)

Saturday, December 2nd and Sunday, December 3rd

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Don't miss the festive lights and live excitement of the CP Holiday Train from Montreal, Quebec. Since 1999, the trains have raised more than $13 million and four million pounds of food for communities along its routes.

The Holiday Train is about 1,000 feet in length with 14 brightly decorated rail cars. Each car is decorated with hundreds of thousands of technology-leading LED lights and holiday designs.

At each stop, after the illuminated train arrives and pulls to a safe stop in front of the crowd, the stage door lowers and the live music begins. This year, fans will enjoy performances of holiday themed songs by Terri Clark, Dallas Smith and Kelly Prescott. There will also be a brief presentation with local food bank officials and dignitaries. Once the band plays its farewell song, the stage door closes, and the train heads off to the next stop. Each stop lasts about 30 minutes.

Each event is completely free, and attendees are encouraged to bring monetary or healthy food bank donations to help alleviate hunger in their own local community. Stops in Southeastern Wisconsin this year are:

Saturday, December 2nd

Sturtevant

9900 East Exploration Ct., Amtrak Depot

5:25 p.m. - 6:05 p.m.

Milwaukee

433 West St. Paul Avenue, Amtrak Depot

6:50 p.m.0 7:45 PM

Sunday, December 3rd

Wauwatosa

Harwood Avenue crossing

4:15 p.m. - 5:00 p.m.

​Hartland

Level Crossing at Cottonwood Avenue

5:45 p.m. - 6:30 p.m.

Oconomowoc

South Main Street railway crossing

6:55 p.m. - 7:25 p.m.

Watertown

Brandt Quirt Park parking lot (ball diamond), adjacent to track

7:45 p.m. - 8:30 p.m.

#3. Christmas in the Ward (Free!)

Friday, December 1st and Saturday, December 2nd

Historic Third Ward

6:05 tree lighting ceremony on Friday

On Friday, watch a magical tree lighting in Catalano Square at 6:05 p.m., meet live reindeer with Mrs. Claus, try actual chestnuts roasting on an open fire, take horse drawn carriage rides, see costumed characters, sip hot cocoa, and more. You can visit with Santa in Jolly’s Outdoor Gingerbread House, too. Plus, for the adults, don't miss their "cocoa cocktails"!

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#4. West Allis Christmas Parade (Free!)

Saturday, December 2, 2017

4:45 p.m.

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The West Allis Christmas Parade is an annual holiday tradition, and the only night-time Christmas parade in Southeast Wisconsin! Enjoy marching bands and live performers, creative floats and vintage vehicles, meet elves, cartoon characters, and of course, wave to Santa Claus himself at the end of the parade.

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Experience Christmas on the Avenue prior to the parade. Christmas on the Avenue begins at 1:30 p.m. and features children and family activities, crafts, games and more. Festivities will conclude at 3:30 p.m. Christmas caroling and the annual Christmas tree lighting ceremony will begin at 4:00 p.m. at the West Allis Centennial Park Plaza on 76th and Greenfield Avenue.

This year’s theme is “Rockin’ Around the Christmas Tree,” a rollicking, rocking, rolling celebration of the season!

#5. Kohl's Art Generation Family Sunday

Sunday, December 3rd

Milwaukee Art Museum

10:00 - 4:00

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Deck the walls . . . with art! Create drawings, prints, and paintings inspired by master artists in the exhibition Degas to Picasso: Creating Modernism in France. Learn a few words en francais, enjoy French tunes by the Wisconsin Conservatory of Music’s Suzuki Ensemble, and more. Kohl’s Art Generation Family Sundays are free with Museum admission, and kids 12 and under are free every day the Museum is open thanks to Kohl’s Cares. Free for Museum members as well as Boys and Girls Club of Greater Milwaukee members.

Christmas with kids and families in Milwaukee

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