The holidays have arrived in Downtown Milwaukee, and there’s no better time to explore holiday markets, glowing decorations and businesses that make our city special. Whether you’re searching for gifts, planning a family outing, or simply soaking in the seasonal spirit, here are five reasons to make downtown your holiday destination.
Shop Small & Support Local
Downtown offers some of Milwaukee’s most unique holiday shopping experiences, making it easy to find thoughtful, locally made gifts. The Milwaukee Makers Market will host its Holiday Showcase at the Discovery World Pavilion on December 21 from 10 a.m. to 4 p.m., bringing together dozens of local makers under one roof. Earlier in the month, the MIAD Holiday Sale returns December 4–6, featuring original artwork, prints, jewelry, ceramics, and more created by MIAD students, alumni, and faculty. Shopping small not only helps you discover one of a kind gifts – it directly supports Milwaukee’s creative community.
Winter Decor
Downtown Milwaukee transforms into a winter wonderland each December, offering countless moments of holiday joy. Community Spirit Park in Cathedral Square is filled with over 100 evergreen trees decorated by local organizations and festive light displays perfect for photos. Just steps away, The Ornament Trail adorns Wisconsin Avenue, as well as select locations on Water Street and nearby neighborhoods with a series of oversized ornaments hand-painted by local and nationally renowned artists with Milwaukee ties. Bundle up, grab a warm drink from a nearby café, and enjoy the installations that brighten our streets all season long.
Holiday feasts
If festive dining is on your wishlist, downtown restaurants provide unforgettable holiday experiences. For those looking to celebrate the holidays without turning on the oven, celebrate Christmas at Mason Street Grill or Saint Kate – The Arts Hotel, where special Prix Fixe Menus are served on Christmas Eve and Christmas Day. From intimate dinners to family feasts, downtown makes holiday dining effortless and memorable.
Seasonal sips
Holiday pop-up bars bring an extra dose of seasonal magic to the heart of the city. Sip’n Santa at Pufferfish Tiki delivers a tropical spin on holiday cheer with themed cocktails and playful décor, while Miracle on 2nd at The Tin Widow leans into classic Christmas nostalgia with twinkling lights, festive drinks, and over-the-top holiday charm. These limited-time experiences are perfect for a night out with friends or a fun stop before a show.
Family-Friendly Festivities
Downtown Milwaukee also offers fun traditions for the whole family. Cocoa with the Clauses returns to Cathedral Square Park on Saturday, December 13, giving kids the chance to meet Santa and Mrs. Claus, sip hot cocoa, and enjoy the holiday atmosphere. Saint Kate – The Arts Hotel will also host its annual Brunch with Santa on December 13 and 14, creating a magical experience complete with photos, treats, and plenty of Christmas spirit. These events are ideal for making cherished holiday memories with loved ones.
With festive décor, small business shopping, local dining, and family activities, Downtown Milwaukee is full of reasons to celebrate the season. Make a day of it or visit again and again to enjoy everything the holidays have to offer.