Holiday Happenings

***Please note, events and activities are subject to change or cancellation. Please call ahead of your arrival.***

Santa’s Mailbox

Sponsored by Educators Credit Union
With support from Serving Older Adults & Letter Carriers Union Branch 2
November 7 – December 17
Cathedral Square Park
414.220.4700 |
Place a child’s letter to Santa in Santa’s Mailbox. Be sure to include a return address because Santa and his extra special helpers will ensure each child receives a personalized reply. Holiday spirit delivers the letters – no postage is required!

Ornament Trail

November 6 – January 6, 2024
Wisconsin Avenue & Water Street
414.220.4700 |
Explore 15 larger-than-life, hand-painted ornaments by locally and nationally renowned artists.

Deck the Streets and Village

November 10 – January 22, 2023
Milwaukee Public Museum
414.278.2728 |
Experience the magic of the holiday season inside two of MPM's most beloved exhibits, Streets of Old Milwaukee and European Village, where the walkthrough turn-of-the-century streetscapes are transformed into holiday wonderlands.

Milwaukee Holiday Lights Festival Kickoff Extravaganza

Thu, November 16 | 6:30pm
Pre-show fun starting at 5:30pm
Pere Marquette Park
414.220.4700 |
Music, dancing, Santa and a thrilling fireworks display combine for the brightest night of the year. Best of all, it’s free – right down to the treats and Jingle Bus rides.

110th Annual City Christmas Tree Lighting

Fri, November 17 | 5pm to 7pm
Deer District
Gather with family and friends to see the 110th annual Milwaukee Christmas tree lighting: an event in partnership with local entertaining and style expert David Caruso and the City of Milwaukee Department of Public Works Forestry Division.

Jingle Bus Tours

November 17 – December 30
Thu & Fri | 6pm to 9pm
Sat | 5pm to 9pm
Sun | 5pm to 8pm
Courtyard Milwaukee Downtown - 300 W Michigan Street
414.220.4700 |
Marvel at Downtown’s spectacular sights aboard the convenient Jingle Bus. For $5 per person, visitors can relish in the festive panorama while a narrator shares stories of the jolliest attractions and landmarks. Tickets must be purchased in advance online. Spanish tours also available.
Wisconsin Avenue lights photo courtesy of VISIT Milwaukee

B93.3 Letters to Santa Mailbox

November 17 - December 20
Deer District Plaza near The MECCA
Stop by B93.3's Santa Mailbox this holiday season, located at Cheer District, illuminated by We Energies Foundation. Bring the family down and send your holiday wishes to the North Pole! 

FEZtival of Trees

November 18 – 25
Tripoli Shrine Center
414.933.4700 |
Walk through a wonderland of trees decorated by local businesses and organizations, snap a photo with Santa and enjoy a light show during the week of Thanksgiving. Then, place a bid for a chance to win a fully decorated tree to take a piece of the holiday spirit home with you.

Holiday Snow Globe

November 18 – January 7, 2024
Mitchell Park Domes
414.257.5600 |
This holiday season, enjoy the warmth of the domes amid a snowy field of hundreds of poinsettias. Bring your loved ones into a polar paradise of playful animals enjoying the winter season and preparing for the holidays. Visit with Santa on special occasions and experience the rare treat of the “northern lights” on late nights at the conservatory. This is truly a gift for everyone.

Milwaukee Makers Market

Sat, November 18
Deer District's The Beer Garden
Shop local this holiday season! The Milwaukee Makers Market will take place in The Beer Garden on Nov. 18 from 11am-4pm. This market is free to all and will feature a variety of seasonal selections including knitwear, pastries, artwork and more! 


Cream City Creatives Holiday Market

Sun, November 19 | 10am to 3pm
Turner Hall Ballroom
This annual holiday market has been bringing Milwaukee to life with creativity since 2014. Shop from dozens of vendors offering local goods that make perfect gifts for family and friends.

The Journeyman Hotel Holiday Events

November & December
The Journeyman Hotel
1.855.KIMPTON |
Kicking off with Friendsgiving Night Out on Nov. 22 – drink specials in The Uutsider for you and your pals and a Thanksgiving Feast Buffet at Tre Rivali on Thanksgiving Day — the hotel will also welcome back the seasonal bears to the rooftop on Dec. 1 as that transitions into a cozy fireside destination. Plus, don’t miss the hotel’s tree lighting ceremony on Dec. 10, featuring live music in the lobby and fireside drink specials at The Outsider. A Christmas Day buffet at Tre Rivali, New Year’s Eve party (with a DJ, open bar, buffet, photo booth and fortune teller), and New Year’s Day brunch top off the holiday season in style.

Pfister Hotel Thanksgiving Bountiful Brunch

Thu, November 23 | 10am to 2:30pm
The Pfister Hotel
414.273.8222 |
Immerse yourself in the breathtaking atmosphere of the Pfister Grand Ballroom, the perfect destination for your family’s cherished Thanksgiving. There is much to be thankful for, from appetizers and entrees to side dishes and desserts, plus all the traditional trimmings.

Milwaukee Turkey Trot

Thu, November 23 | 9am
Veterans Park
Join the flock during the annual Turkey Trot. It’s your pre-turkey workout. Your body will thank you later!

Thanksgiving at Mason Street Grill

Thu, November 23 | 1pm to 8pm
Mason Street Grill
414.298.3131 |
Enjoy an all-American grill for this quintessential holiday with wood-grilled steaks, seafood and a special Thanksgiving prix fixe menu. Private dining rooms are also available.

Thanksgiving Harvest Dinner

Thu, November 23 | 11am to 7pm
ARIA at Saint Kate – The Arts Hotel
414.270.4422 |
Experience an Artisanal American Thanksgiving at ARIA. Enjoy a special prix fixe menu featuring special dishes, as well as traditional Thanksgiving favorites.

Explorium Brewpub Black Friday MCS Release

November 24-26
414.423.1365 |
Join Explorium all Thanksgiving weekend for its annual Black Friday MCS release, live music, local artwork, holiday gift deals, food discounts, and FREE brewery tours. 

Sippin' Santa 

November 24 - December 30 | 5pm to 1am
PufferFish at Hotel Metro
414.272.1937 | 
Famed Christmas-themed cocktail pop-up bar, Sippin' Santa is coming to Milwaukee for the 2023 holiday season. PufferFish (411 E. Mason St.) will become the first Sippin' Santa bar in the city's history. This popular downtown rooftop bar will transform into a winter wonderland, complete with Tiki inspired holiday drinks. In addition, the presidential room at Hotel Metro will be converted into The Santa Suite. To book, go to This hotel package is available from November 15 - December 30, 2023.  


Letters to Santa at the Pfister

November 24 – December 17
The Pfister Hotel
414.273.8222 |
Write a letter to Santa and drop it off at The Pfister Hotel North Pole Mailbox. Each child will receive a personalized note from Santa himself, plus all children will receive a free cookie from the Pfister front desk when they drop off their letters.

Twilight Tours

November 24 – December 30
Pabst Mansion
414.931.0808 |
A holiday tradition the whole family can enjoy! Delight in the wonderment of Christmas at the Pabst Mansion, where no two Christmases are the same. From glitz and glam to train tracks and teddy bears around the tree, each room is decked from tip to mistletoe.

Small Business Saturday

Sat, November 25
Historic Third Ward
414.273.1173 |
Explore the unique offerings around the Historic Third Ward as you #shopsmall. Stop into the many independent businesses in the neighborhood to check off goodies on your gift list.

Milwaukee Makers Market

Sat, November 25 | 10am to 4pm
Sun, December 17 | 10am to 4pm
Discovery World
414.765.9966 |
Support local crafters, artists and creators by browsing dozens of booths featuring clothing, visual art, candles, home goods and so much more. This no-charge-to-enter artisan showcase is the perfect opportunity to shop for co-workers, pets, uncles, aunts and everyone in between.

Milwaukee Pets Alive Crafty Christmas Fundraiser

Sat, November 25 | 10am-4pm
MARN Art & Culture Club
This is a unique craft and gift sale raising much-needed funds for the special needs and considerations animals that Milwaukee Pets Alive rescues. 100% of the sale of each item will benefit Milwaukee Pets Alive to help our very special rescued animals!

Holiday Outlet

Presented by MIAD Gallery at The Avenue
November 25 - December 21
414.847.3208 |
MIAD Gallery at The Ave presents its first-ever Holiday Outlet, your destination to shop works from local creatives this holiday season. The Holiday Outlet will begin on Small Business Saturday, Nov. 25, with an official hot chocolate kick-off (while supplies last!), raffle, and a first-look at creative gifts for yourself and others.

Father Christmas Visits the Mansion!

November 26 – December 25 | Sun | 2:30pm
Pabst Mansion
414.931.0808 |
With his lantern, walking stick and red cloak with white trim, a whimsical Father Christmas travels south to visit the Pabst Mansion each Sunday during the holiday season. Create magical memories with holiday treats, letters to Santa, and room after room of enchanting Christmas displays.

A Christmas Carol Dinner Experience

Wed, November 29 | 5pm
The Dark Room at Saint Kate – The Arts Hotel
414.276.8686 |
Reserve your spot for a wonderful winter's evening! Your reservation includes an exclusive meal with a menu curated by Executive Chef Erik Hansen. In addition to your meal, your reservation also includes a ticket to that evening's performance of “A Christmas Carol,” next door at the Pabst Theater, with seats located in the center orchestra section on the main floor.

MIAD Holiday Sale

November 30 – December 2
Milwaukee Institute of Art and Design
888.749.MIAD |
Each year during the first week of December, MIAD students and alumni show off their wares ranging from sculptures, paintings and photographs to jewelry, stickers, greeting cards and more. Shop their affordable offerings and view the on-campus galleries while you visit.


Slice of Ice

Presented by WaterStone Bank
December – Mid-March, 2024
(weather permitting)
Red Arrow Park
414.289.8791 |
As weather permits, Milwaukee County Park's "Slice of Ice" skating rink will open for the winter season in the heart of downtown Milwaukee.

Christmas in the Ward

Fri, December 1 | 5:30pm to 8:30pm
Catalano Square
414.273.1173 |
Dash into the holiday season with festivities under the Historic Third Ward’s Christmas Tree. This night is packed with live entertainment, photo ops alongside Santa and his reindeer, food trucks, fireworks and local shopping.

Christmas Lights & Desserts Bus Tour

Fri & Sat | December 1 – 22
Various Locations
414.255.0534 |
Check out the dazzling light displays around Milwaukee with pit stops for cocoa, seasonal snacks, and photo ops!

Christmas Around Milwaukee Bakery Tour

Fri – Sun | December 2 – 22
Various Locations
414.255.0534 |
Spend the day sampling Christmas cookies, candies and pastries from some of Milwaukee’s finest bakeries. The tour includes 5-7 stops, and you get bonus good Santa juju if you dress up!

Santa’s Christmas Cavalcade

Sat, December 2 | Departs at 5pm
Fri, December 8 | Departs at 5pm
Downtown Milwaukee
414.220.4700 |
See Santa and Mrs. Claus on the festive route riding atop a vintage fire truck. Sarah Fierek will also be on board singing jazzy holiday tunes. On Dec. 2, the Cavalcade will feature a Black Santa. The route departs from the Milwaukee Public Market and travels throughout downtown.

Breakfast with Santa at The Starling

Sun, December 3 | 9am & 11am
The Starling
Feast on fluffy pancakes, savory scrambled eggs, crispy bacon, and sizzling sausage links, all alongside delightful locally sourced Holiday donuts. Sip on your choice of coffee, milk, hot chocolate, or refreshing orange juice.


Santa Cycle Rampage

Sat, December 2
Various Locations
Join the world's largest holiday-themed costume group bicycle ride, with proceeds benefiting the Wisconsin Bike Fed.
Santa Cycle Rampage photo courtesy of VISIT Milwaukee

Hover Craft: Handmade Holiday Shopping Extravaganza

Sun, December 3 | 12pm to 6pm
Pritzlaff Building
Milwaukee’s creative community comes together for the 13th year of Hover Craft brimming with one-of-a-kind handiwork. Thousands of shoppers peruse this holiday showcase, so snag your ticket to shop online in advance.

Milwaukee Public Market Holiday Events

All throughout December
Milwaukee Public Market
The Milwaukee Public Market will host a variety of holiday-themed events throughout the season, including holiday-themed cooking, baking and hot cocoa classes; celebrity bell ringing on Dec. 6; Breakfast with Santa on Dec. 9; and more!

Holiday Lights on the Hoan

December 7 - 15
December 24 & 25
Sun, December 31
Hoan Bridge
Enjoy Friday Night Lights through the end of the year beginning at 7pm, plus enjoy Hanukkah on the Hoan (Dec. 7 - 15), Christmas Light Shows (Dec. 24 & 25) and an NYE Countdown (Dec. 31).


Breakfast with Santa Saturdays

December 9 & 10, 16 & 17
The Pfister Hotel
414.273.8222 |
The Pfister Breakfast with Santa is a holiday tradition that creates lifelong memories. Guests can share a jolly breakfast selection with Santa and his elves in The Pfister’s festive ballroom. Seatings are available at 8:30am and 11am.

Saint Kate Holiday Marketplace

December 9 – 10 | 11am to 4pm
Saint Kate – The Arts Hotel
414.276.8686 |
Experience and enjoy the holiday ambiance of Saint Kate while interacting and connecting with local artists and vendors. You'll find over 100 Milwaukee-area artists throughout the hotel.

Cocoa with the Clauses

Presented by Madison Medical Affiliates
Sat, December 9 | 11am to 2pm
Cathedral Square Park
414.220.4700 |
Santa and Mrs. Claus return for this annual cocoa klatch. The free outdoor event is a chance for kids to share their wish lists and for moms and dads to grab a keepsake photo. Elves and other holiday characters will also be there! Plus, complimentary cookies and hot cocoa will be provided.

Holiday Sweater Party

Sun, December 10 | 6pm - 10pm
Explorium Brewpub
414.423.1365 |
Join Explorium for an ugly sweater contest, prizes, drink specials, beer flights, live music, and a Mug Club gift exchange at your favorite neighborhood brewpub. Visit for more details.


Christmas at the Milwaukee County Historical Society

Sun, December 10 | 10am to 1pm
Milwaukee County Historical Society
414.273.8288 |
Join the Milwaukee County Historical Society for a family-favorite holiday celebration. Families can get their picture with Santa, create an ornament, enjoy treats and more.

Wisconsin LGBT Chamber’s Holiday Soiree

Thu, December 14 | 4:30pm - 7pm
Vue Rooftop Ballroom at Hyatt Regency Milwaukee
414.678.9275 |
Raise a glass of cheer to the festive season during this swanky holiday party. Enjoy drinks and hors d’oeuvres as you mingle with LGBT-owned and allied businesses.

Brunch with Santa

December 16 & 17, 22 & 23
Saint Kate – The Arts Hotel
414.276.8686 |
Start a new holiday tradition at Saint Kate's "Brunch With Santa" and create lifelong memories! Guests will have the opportunity to experience a plentiful brunch in Saint Kate's festive ballroom and visit with the jolly man himself. There will be chefs in the room griddling up waffles with all the trimmings, along with traditional buffet favorites.

Supper with Santa

Sat, December 16 & 22 | 6pm to 7:30pm
Saint Kate – The Arts Hotel
414.276.8686 |
Experience a magnificent dinner in Saint Kate's festive ballroom, topped off with a visit from the jolly man himself! In addition to the opportunity to take photos with Santa, every child will receive a special gift, and will be able to make crafts and write their own letter to Santa.


ARIA Christmas Dinner

Sun, December 24 | 2pm to 9pm
Mon, December 25 | 10am to 8pm
ARIA at Saint Kate – The Arts Hotel
414.270.4422 |
Experience delicious holiday specialties steeped in the culinary tradition of the Midwest. Enjoy festive offerings inspired by all the comforts of a home-cooked feast, in addition to ARIA’s regular menu.

Holiday Lights on the Hoan

December 7-15
December 24 & 25
Sun, December 31
Hoan Bridge
Enjoy Friday Night Lights through the end of the year beginning at 7pm, plus enjoy Hannukah on the Hoan (Dec. 7 – 15), Christmas Light Shows (Dec. 24 & 25) and an NYE Countdown (Dec. 31).

Christmas Celebration Brunch

Mon, December 25 | 9am to 1:30pm
The Pfister Hotel
414.273.8222 |
A Pfister Christmas brunch begins with a complimentary mimosa or bloody mary in the elegantly decorated ballroom. Following cocktails is a spectacular buffet!
Pfister Hotel photo courtesy of VISIT Milwaukee

Mason Street Grill Christmas

Mon, December 25 | 1pm to 8pm
Mason Street Grill
414.298.3131 |
Experience classic American favorites and enjoy delicious Christmas specials in addition to the regular menu. Private dining rooms are also available for your family gathering, big or small.

Afternoon Tea at The Pfister

Fri – Sun, Ongoing
The Pfister Hotel – Blu
414.935.5950 |
Treat your family and friends to a relaxing afternoon experience with an incredible panoramic view of downtown. You’ll feel like royalty with tea, sandwiches and pastries served on silver platters by a Pfister tea butler. Reservations required.