12 Days Of Cheer In Oak Creek: 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 Oak Creek. 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 Oak Creek 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. Witness the city aglow at the Milwaukee Holiday Lights Festival.

Just a short drive from Oak Creek, downtown Milwaukee transforms into a glittering spectacle with over half a million lights from November 20 through January 1. You can stroll through the brilliant displays at Cathedral Square Park, Pere Marquette Park and Zeidler Union Square, or hop on the Jingle Bus for a guided tour (running Fridays through Sundays). It’s a “glowrious” way to celebrate the season, though advance tickets are recommended if you plan to ride the bus.

2. Sip seasonal brews in a historic schoolhouse at Hillside Coffeehouse.

Located in a charmingly restored old schoolhouse, Hillside Coffeehouse is the perfect spot to warm up with a cup of Anodyne Coffee or Rishi Tea. Locals love the relaxed atmosphere and the selection of fresh cupcakes, cookies and tarts that make for a sweet winter treat. Be sure to keep an eye on their Facebook page, as they have been known to host festive pop-up events during the holiday season.

3. Soak up local history and hospitality at The Cellar Pub & Grill.

For a laid-back evening, visit The Cellar Pub & Grill, a true Oak Creek icon housed in a building that dates back to the 1860s. Known for its friendly “enter as strangers, leave as friends” vibe, this spot offers nightly dinner specials and 50-inch TVs perfect for watching the game. It’s a great place to escape the cold, enjoy a pizza or sandwich and experience a piece of local history on Oakwood Road.

4. Glide across the ice at Wilson Ice Arena.

When the temperatures drop, head over to Wilson Ice Arena for some active winter fun on their NHL-sized rink. Public skating is available on most days (typically starting at 11 AM on weekdays and 2:30 PM on Saturdays), making it an easy afternoon outing for families or groups. Admission is affordable–around $6.75 for adults and $5.00 for juniors (17 and under)–and skate rentals are available on-site i you don’t have your own pair.

5. Hunt for one-of-a-kind gifts at Serendipity Boutique Marketplace.

If you are looking to shop small this December, Serendipity Boutique Marketplace brings local businesses, artists and designers together under one roof. It is the perfect place to stumble upon something unexpected, from handcrafted home goods to unique accessories you won’t find in big-box stores. Strolling through the stalls is a great way to support local creativity while crossing names off your holiday gift list.

6. Walk on the wild side at the Milwaukee County Zoo’s Wild Lights.

Experience the zoo in a whole new light–literally–during the Wild Lights event, running on select dates from November 21 through December 31. Visitors can walk through the forest and pathways illuminated by hundreds of thousands of sparkling lights and animal-themed displays. Be sure to buy your tickets in advance and check out the event calendar for all the fun.

7. Explore the heart of the community at Drexel Town Square.

Functioning as Oak Creek’s modern downtown, Drexel Town Square offers a blend of retail, dining and nature that is perfect for a December day out. You can bundle up for a walk along the wetlands trails to enjoy the winter landscape, then head to Main Street to warm up at one of the many restaurants or shops. It is a convenient hub where you can run errands, grab a bite and enjoy the fresh air all in one stop.

8. Experience a timeless holiday tale at The Pabst Theater.

Make the short trip into the city to see the Milwaukee Rep’s production of A Christmas Carol, a beloved tradition running from November 25 through December 24. Set in the historic Pabst Theater, the 2-hour and 10-minute show features beautiful scenery, special effects and Matt Daniels returning as the iconic Ebenezer Scrooge. It’s a heartwarming production suitable for ages 6 and up that captures the true spirit of redemption and hope.

9. Step back in time at the Milwaukee Public Museum.

From November 16 through January 25, the Milwaukee Public Museum decks out its famous “Streets of Old Milwaukee” and “European Village” exhibits with period-appropriate holiday decor. You can learn about European traditions from costumed docents or catch special events like the Florentine Opera Holiday Concert on December 8. Saturdays in December are particularly festive, offering “Holidays in History” tours that explore how immigrant traditions blended to create modern celebrations.

10. Find the perfect handmade treasure at Swoon.

For a shopping experience focused on quality and craftsmanship, visit Swoon, a gift shop specializing in items made by local and national artists. Open daily until 7 PM through December 23, the shop is filled with heirloom-quality toys, handmade jewelry and locally poured candles perfect for the holiday season. It’s an ideal spot to find a thoughtful, non-commercial gift while supporting the local art community.

11. Bowl a strike and shop local at Classic Lanes.

Classic Lanes is more than just a spot for bowling and arcade games; this December, they are hosting a special “Shopping in a Winter Wonderland” event. On December 14 from 11 AM to 3 PM, you can browse wares from over 30 local vendors, making it a fun combination of entertainment and holiday prep. Whether you are there for the craft fair or just to knock down some pins, it’s a lively place to spend a winter afternoon.

12. Drive through the spectacular display at Candy Cane Lane.

A massive volunteer effort in West Allis, Candy Cane Lane features over 300 homes decorated to the nines from November 28 through Christmas Day. This neighborhood light show is a major fundraiser for the MACC Fund, supporting childhood cancer research, so be sure to look for volunteers with donation buckets as you drive or walk the route (96th to 92nd St.). Lights are on every evening, and if you visit between December 6 and 23, you might even spot Santa greeting the crowds.

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

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