101 Ideas for Holiday Family Fun in Milwaukee - 2026
Santa Sightings
| Nov 29 - Dec 24, 2026 | Father Christmas Visits the Pabst Mansion - Pabst Mansion |
| Dec 6 - 20, 2026 | Breakfast With Santa at the Harley-Davidson Museum - Harley-Davidson Museum® |
| Dec 12, 2026 | Festivals of Cedarburg: Santa's Dash Away 5K - W63N641 Washington Ave. Cedarburg, WI |
Light Displays
| Nov 19, 2026 - Jan 1, 2027 | Milwaukee Holiday Lights Festival 2026 - Downtown Milwaukee |
| Nov 21, 2026 - Jan 30, 2027 | Christmas Carnival of Lights 2026 - Christmas Carnival of Lights |
| Nov 27 - Dec 24, 2026 | Enchantment in the Park - Regner Park |
| Nov 27, 2026 | Annual Pfister Tree Lighting Ceremony - The Pfister Hotel |
| Dec 4, 2026 | Light the Square - City of Oak Creek - Drexel Town Square |
| Dec 4, 2026 | Hartland Lights and Drone Show - Village Square |
Shopping & Craft Fairs
| Nov 21, 2026 | Celtic Christmas Boutique - CelticMKE Center |
| Nov 21 - 28, 2026 | 9th Annual Tripoli Shriners FEZtival of Trees - 3000 W Wisconsin Ave, Milwaukee, WI |
| Nov 25 - 29, 2026 | Oconomowoc German Christmas Market - 174 East Wisconsin Avenue, Oconomowoc, WI |
| Nov 28, 2026 | Menomonee Falls Downtown Presents Small Business Saturday - See website for specific locations. |
| Dec 5, 2026 | Holiday Boutique at Hawthorn Hollow, Nature Sanctuary and Arboretum - Hawthorn Hollow Nature Sanctuary & Arboretum |
| Dec 6, 2026 | 2026 FBBG Holiday Gift Fair - Boerner Botanical Gardens |
| Dec 11, 2026 | Oak Creek Christmas Market - Drexel Town Square |
| Dec 12, 2026 | Menomonee Falls Christkindl Market - Presented by Bank Five Nine - Mill Pond Park, Centennial Plaza, Downtown District shops and eateries |
Holiday Theatre
| Nov 21 - Dec 27, 2026 | DR. SEUSS'S HOW THE GRINCH STOLE CHRISTMAS! - Marcus Performing Arts Center |
| Dec 2 - 24, 2026 | A Christmas Carol - Milwaukee Repertory Theater - The Pabst Theater |
| Dec 11 - 13, 2026 | Cirque Dreams Holidaze - Miller High Life Theatre |
| Dec 13, 2026 | The Night Before Christmas Children's Reading - Villa Terrace Museum & Gardens |
Holiday Concerts
| Dec 6, 2026 | Mannheim Steamroller Christmas by Chip Davis - Miller High Life Theatre |
| Dec 19, 2026 | Sean Heely's Celtic Christmas - Marcus Performing Arts Center |
Old-Time Christmas
| Dec 5 - 13, 2026 | Home for the Holidays at Old World Wisconsin - Old World Wisconsin |
Train Fun
| Dec 5, 2026 | Christmas Parade Train - East Troy Railroad Museum - Visit website for exact route. |
Hands-on Holiday Fun
| Dec 4 - 5, 2026 | Menomomee Falls Downtown Cookie Crawl - Downtown Menomonee Falls |
| Dec 7, 2026 | Upcycled Cork Ornaments at Boerner Botanical Gardens - Friends of Boerner Botanical Gardens |
Active Holiday Fun
| Dec 19, 2026 | Candy Cane Course - MILWAUKEE - Milwaukee County Sports Complex |
Christmas Tree Experience
| Nov 21 - 28, 2026 | 9th Annual Tripoli Shriners FEZtival of Trees - 3000 W Wisconsin Ave, Milwaukee, WI |
Festivals
| Nov 14, 2026 | Germantown Christmas Festival Parade & Christmas in the Park - Firemen's Park |
| Dec 5, 2026 | Oconomowoc Christmas Parade - 174 East Wisconsin Avenue, Oconomowoc, WI |
Miscellaneous
| Nov 19, 2026 - Jan 3, 2027 | Christmas at the Pabst Mansion - Pabst Mansion |
| Dec 5, 2026 | Christmas at the Museums! - Kenosha Public Museum and Civil War Museum |
| Dec 31, 2026 | Noon Years Eve - 174 East Wisconsin Avenue, Oconomowoc, WI |
Christmas Tree Farms
Shopping for a Christmas tree? Here's our list of farms where you can purchase your own Christmas tree in the Milwaukee area.
Subscription Boxes: Gifts That Keep on Giving
Send thoughtful choices to the ones you love near and far, and plan some excellent expected surprises for your own family in the months to come. KidsOutAndAbout has put together of some of our favorite choices with a range for all different ages and interests.
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