Looking for free holiday events in Milwaukee? You’re in luck – the city shines extra bright this time of year! From twinkling light displays and cozy cocoa moments to festive parades and Santa sightings, there are countless ways to celebrate without spending a dime.
Here’s your ultimate guide to Milwaukee’s best free Christmas activities and holiday events for families in 2025.
Want even more? Don’t miss our Milwaukee Holiday Fun Guide and Free Things To Do with Kids in Milwaukee for year-round inspiration!
1. Christmas in the Ward
📅 December 5, 2025
📍 Catalano Square
Kick off the season at Christmas in the Ward, one of Milwaukee’s most festive traditions. Enjoy live music, reindeer, costumed characters, light displays, and family-friendly entertainment throughout the Third Ward.
2. Downtown Milwaukee Holiday Lights Festival
📅 November 20, 2025- January 1, 2026
📍 Downtown Milwaukee
Milwaukee’s most dazzling holiday lights display takes over downtown with illuminated parks, themed displays, and free family fun.
Highlights:
- Kickoff Extravaganza: Nov. 20, 6:30 p.m., Pere Marquette Park — Live music, dancing, fireworks, and free cocoa and cookies.
- The Ornament Trail: Nov. 20 – Jan. 18 — Follow a trail of 20 larger-than-life ornaments hand-painted by local artists.
- Santa’s Mailbox: Nov. 10 – Dec. 14, Cathedral Square Park — Drop off your child’s letter to Santa (no postage required) and get a personalized reply!
- New this year: The Jingle Bus departs from a cozy Warming House at Red Arrow Park, featuring cookies, cocoa, Biggby Coffee, and restrooms for riders.
3. City of Milwaukee Christmas Tree Lighting
📅 November 21, 2025 | 5–7 p.m.
📍 Deer District, Fiserv Forum Plaza
See the city sparkle at the 112th annual Milwaukee Christmas Tree Lighting. Enjoy live performances, free hot cocoa, and a visit from Santa and his reindeer. Plus, there’s a brand-new Holiday Market at Deer District, replacing the Tosa Holiday Market this year.
👉 Explore even more tree lighting events in our Milwaukee Tree Lightings Guide.
4. Holiday Window Display Unveiling (NEW for 2025)
📅 Saturday, Nov. 22, 2025 • 12–2 p.m
📍Milwaukee Public Market – St. Paul Avenue Sidewalk
Kick off the season with the Public Market’s first-ever Holiday Window Display, created in partnership with MIAD. The entire St. Paul Avenue sidewalk becomes a festive open-air gallery with ten large-scale, student-designed installations. Opening day includes free hot cocoa, live caroling by Milwaukee Rep (every hour), a letter-to-Santa station, and a chance to meet the artists. The displays stay up through January 31.
5. Miller Valley Holiday Lites (Dates TBD)
📅 2025 Dates Coming Soon
📍Plank-Road House at 3897 W. State St.
A classic Milwaukee holiday tradition, the Miller Brewery lights up with thousands of sparkling bulbs and animated displays. It’s a must-see stop for local families each season.
6. Candy Cane Lane (November 28 – December 25, 2025)
📅 November 28-December 25, 2025
📍 W Oklahoma Ave, West Allis, WI 53227
Drive or stroll through Candy Cane Lane, a beloved neighborhood where residents go all out with holiday lights. Donations benefit the MACC Fund, supporting childhood cancer research.
7. Ice Skating at Red Arrow Park
📅 Opening Dates Coming Soon
📍 920 N Water St, Milwaukee, WI 53202
Bring your own skates and glide for free under the city lights at Slice of Ice. Rentals are available for a small fee, and nearby cafes offer warm cocoa to complete the outing.
8. Cocoa with the Clauses
📅 Saturday, December 13, 2025
📍 Cathedral Square Park
Spend an afternoon sipping cocoa with Santa and Mrs. Claus in Cathedral Square Park. Cocoa With the Clauses is a heart-warming (and wallet-friendly!) event that lets kids share wish lists and snap festive photos.
9. CP Holiday Train (December 9-11, 2025)
📅 December 9-11 2025
📍 Various Stops
The iconic Canadian Pacific Holiday Train rolls through Milwaukee, glowing with lights and live performances. Donations collected at each stop support local food banks.
10. Parade of Gingerbread Houses
📅 2025 Dates Coming Soon
📍 Milwaukee Public Market
Marvel at intricate gingerbread houses designed with love and holiday spirit. A treat for the eyes, this display also serves as great inspiration for your own baking adventures. Check out our full roundup of local gingerbread displays.
11. Santa’s Mailbox in Cathedral Square Park
📅 November 10 – December 14, 2025
📍 Cathedral Square Park
Kids can drop letters addressed to Santa, no postage needed! Be sure to include a return address for a magical reply.
Make a day of it: Hop on The Hop Streetcar to reach Cathedral Square Park and stop for cocoa along the way.
👉 Explore even more Santa’s Mailboxes Around Milwaukee.
12. Santa’s Christmas Cavalcade
📅 Saturday, December 6 & Friday, December 12, 2025
📍 Departs from Milwaukee Public Market
Santa’s mobile parade brings holiday cheer to Milwaukee neighborhoods. Keep an eye out for the colorful floats and festive tunes rolling by your block!
Other Holiday Parades in Milwaukee:
- Germantown Christmas Festival Parade – Nov. 15, 2025
- South Milwaukee Christmas at the Commons – Dec. 6, 2025
- Whitefish Bay Holiday Stroll – Nov. 28, 2025
- Waukesha Annual Christmas Parade – Dec. 7, 2025
- Menomonee Falls Christmas Parade – Nov. 30, 2025
- West Allis Christmas Parade – Dec. 6, 2025
- Grafton Christmas Parade – Nov. 29, 2025
- Waukesha Night of Lights – Dec. 5, 2025
- New Berlin Christmas Parade – TBD
👉 Read the full Milwaukee Christmas Parades Guide.
13. Hoan for the Holidays
📅 2025 Dates Coming Soon
📍 Hoan Bridge
Watch one of Milwaukee’s most iconic landmarks glow in holiday colors. The Hoan Bridge light show runs throughout the season, with themed nights and synchronized music.
14. Santa Cycle Rampage
📅 December 6, 2025 | 9:30 a.m.
📍 Various Milwaukee Neighborhoods
Thousands of Santas, reindeer, and elves hit the streets for this festive slow-rolling bike parade. It’s joyful, funny, and free to watch along the route.
15. Holidays on The Hop
📅 December 7, 14 & 21, 2025 | 4–6 p.m.
📍 Downtown Milwaukee
Hop aboard Milwaukee’s free streetcar for live holiday music and sweet treats. Each Sunday features new performers and free cookies for riders.
16. Garden District Winter Wonderland
📍 Garden District Community Garden, 3932 S. 6th St., Milwaukee, WI 53207
📅 Late November – Early January (2025 dates TBA)
Head to Milwaukee’s Garden District for a neighborhood-powered holiday light display that’s as heartwarming as it is beautiful. Each year, local volunteers transform the community garden into a glowing Winter Wonderland, complete with twinkling tunnels of light, decorated trees, and festive wooden cutouts handcrafted by residents.
Want to discover more holiday fun?: Dive into our complete Milwaukee Events Calendar and make the most of the season with top events, hidden gems, and festive outings around Milwaukee.
Calie Herbst, Editor-in-Chief of Milwaukee With Kids, has spent over a decade combining her experiences as a parent of three to create a hub for Milwaukee’s family adventures.
Her decade-long teaching career in Milwaukee Public Schools and academic background, including a Master’s in Teaching from Marquette University and dual B.A.s in Sociology and Spanish from the University of Wisconsin – Madison, fuel her passion for inclusive and engaging family content.
Calie is also a recognized voice in local media, contributing to WISN Channel 12 News, WTMJ Wisconsin Morning News, Fox 6’s Real Milwaukee, and B93.3.
Discover more about Calie’s journey and editorial approach on her About Page and Editorial Policy Page.
