12 Days Of Cheer In Greendale: Making This A December To Remember

The holiday season is officially here, and there’s no shortage of ways to soak up the magic in and around Greendale. To help get you in the spirit, we’ve rounded up a dozen festive ideas you can enjoy throughout the month — each one a fun, joyful way to celebrate the season close to home.

From twinkling light displays and holiday markets to cozy treats, local shopping spots, winter activities and seasonal shows, these 12 picks highlight what makes Greendale feel especially merry this time of year. Whether you check off one or all twelve, it’s all about slowing down, supporting local businesses and making memories.

1. Stroll through the glowing scenes of the Milwaukee Holiday Lights Festival.

From Nov. 20 through Jan. 1, downtown Milwaukee shines with more than half a million sparkling bulbs during the Milwaukee Holiday Lights Festival. Wander through Cathedral Square Park, Pere Marquette Park and Red Arrow Park to see brilliant light displays and festive décor at every turn. For a deeper look at the magic, hop aboard the Jingle Bus for guided tours offered Friday through Sunday in December. Check out the 2025 Festival Guide for full details.

2. Hit the ice during open skate at Wilson Ice Arena.

The Wilson Ice Arena offers daily public skating (except Sundays), giving locals of all ages a festive way to stay active all month long. The NHL-sized rink provides plenty of room to glide, and on-site rentals make it easy for beginners or casual skaters to join in. With weekday open skate times typically starting at 11 a.m. and Saturday sessions beginning at 2:30 p.m., there are plenty of opportunities to add a skating session to your December calendar.

3. See Milwaukee’s favorite holiday tradition, ‘A Christmas Carol,’ at the Pabst Theater.

Running on select dates from Nov. 25 to Dec. 24, the Milwaukee Rep’s production of “A Christmas Carol” fills the historic Pabst Theater with music, dance and timeless holiday storytelling. Beloved local actor Matt Daniels returns as Ebenezer Scrooge in this magical retelling of redemption and holiday spirit. Expect stunning costumes, captivating special effects and a festive atmosphere that makes this a cherished annual outing for families. Tickets are available on the theater’s website.

4. Warm up with a Coquito Latte at Dia Café.

Dia Café on Northway in Greendale offers a vibrant Afro-Caribbean-inspired space that’s perfect for cozy December mornings or mid-shopping breaks. Known for its smooth Coquito Latte and horchata cold brew, this café blends cultural warmth with local charm. Colorful décor and locally roasted blends create a uniquely inviting atmosphere, whether you’re catching up with a friend or recharging during a busy holiday season.

5. Take a drive (or walk) through Candy Cane Lane in West Allis.

From Nov. 28 through Dec. 25, nearby West Allis transforms into Candy Cane Lane, a dazzling neighborhood display featuring more than 300 decorated homes. What began as a small community gesture is now celebrating its 40th year and has raised nearly $4 million for the MACC Fund. Drive or walk the routes between 92nd and 96th Streets and Montana and Oklahoma Avenues and keep an eye out for volunteers collecting donations. Lights are on nightly and hours are posted on the Candy Cane Lane website (subject to change due to weather, traffic and other conditions).

6. Shop one-of-a-kind gifts at Serendipity Boutique Marketplace.

If you’re looking to buy local this holiday season, Serendipity Boutique Marketplace on Broad Street is the perfect place to start. This curated marketplace brings together artists, designers and makers from across the region, offering everything from hand-crafted décor to unique wearable art. It’s a community hub that celebrates creativity, making it an ideal spot for thoughtful holiday shopping or simply browsing with a warm drink in hand.

7. Enjoy craft cocktails and small plates at The Eleanor Room.

Step into Greendale’s past while savoring modern flavors at The Eleanor Room, a chic restaurant honoring First Lady Eleanor Roosevelt and her role in shaping the community. With a creative menu of small plates, craft cocktails and a 300-bottle tequila list, it’s a sophisticated spot for date nights or gatherings with friends. Visit during happy hour (2:00 to 5:00 PM) or enjoy weekend brunch for an extra-special outing.

8. Explore holiday traditions inside the Milwaukee Public Museum.

Now through Jan. 25, the Milwaukee Public Museum brings winter history to life with decorated exhibits, concerts, docent-led tours and hands-on family activities. Stroll through the adorned Streets of Old Milwaukee and European Village exhibits, learn about global holiday traditions or catch special events like the Florentine Opera concert or Cocoa & Candy Canes. Many activities are included with museum admission, though member-exclusive programs may require reservations. See the museum’s ticketing page for pricing and purchase links.

9. Experience a sparkling evening at Wild Lights in the Milwaukee County Zoo.

On select dates from Nov. 21 through Dec. 31, the Wild Lights event transforms the Milwaukee County Zoo into a glowing nighttime wonderland. Wander through forests and pathways illuminated by shimmering animal-themed displays and vibrant light sculptures. With hundreds of thousands of lights, this walk-through experience is both magical and memorable for the whole family.

10. See Milwaukee Ballet’s ‘The Nutcracker’ come to life.

A beloved classic returns Dec. 6 through 26 when the Milwaukee Ballet presents “The Nutcracker” at the Marcus Performing Arts Center. Nearly 200 dancers bring Drosselmeyer’s Imaginarium to life in a production praised as “equal parts smart and magical.” The stunning choreography, enchanting costumes and an immersive holiday atmosphere makes it the perfect festive outing, suitable for all ages.

11. Take a festive day trip to A Cedarburg Christmas.

A 30-minute drive from Greendale lands you in downtown Cedarburg, which is transformed into a Hallmark-worthy holiday destination for the season. The town comes alive with craft fairs, cocoa bars, art exhibits and twinkling displays that draw families from across the region. Visit Santa’s life-size workshop, ride the free trolley or enjoy classic holiday films at the Rivoli Theatre.

12. Tour the beautifully decorated Pabst Mansion during the holiday season.

Experience Milwaukee history wrapped in holiday magic during Christmas at the Pabst Mansion, open daily for self-guided tours. Each room of this grand estate is transformed with uniquely themed décor, from glittering trees to intricate garlands and miniature train displays. The rotating designs mean each year offers something new, making it a tradition worth revisiting. Purchase tickets in advance online or day-of at the Mansion.

Stay warm, shop local and enjoy every twinkling moment — happy holidays, Greendale!

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