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Your Guide to Holidays in the Village

‘Tis the season for Wauwatosa’s first official Holidays in the Village that invites all from near and far to celebrate the season boldly in Wauwatosa, WI. 

When is Holidays in the Village?

From November 16th through December 17th, the heart of our charming city will offer many ways for you to shop local, dine boldly, and relax into the spirit of the season.

What is Holidays in the Village?

With over a month of festivities for those who love to celebrate the season, Holidays in the Village will feature numerous events spread throughout the heart of our charming city. Located in Tosa Village, you’re invited to Sip & Strolls, Small Business Saturday, Wauwatosa Holiday Market, the Canadian Pacific Holiday Train, and The Village Tree Lighting. 

We can’t wait to welcome you to this truly authentic holiday experience that’s unique to Southeast Wisconsin. From artisan makers and small, local boutiques to high-end and big box retailers, Wauwatosa is the go-to destination for all your holiday shopping — complete with countless festive magical moments in between. Celebrate boldly with Wauwatosa’s Holidays in the Village.

Explore Our Festive Events Line-Up

November 16 & December 14: Sip & Stroll

Stroll The Village of Wauwatosa from 5-8PM while sampling beverages and snacks and enjoying in-store specials and discounts. Find great deals on apparel, decor, and fabulous last-minute gifts from our local shops and boutiques

November 25: Small Business Saturday

Whether you’re looking for something specific or hoping that a special gift will catch your eye, Wauwatosa’s small shops and local boutiques are the perfect places to explore during Small Business Saturday. Find holiday specials and in-store promotions all day long. 

Plus, the Holiday Trolley will be running through Tosa Village and to remote parking. 

December 4: Canadian Pacific Holiday Train

The Holiday Train is back with live music and a visit from Santa himself — all to raise funds and gather food donations for Tosa Cares. Admission is free, but please consider donating non-perishable items or a monetary donation to this nonprofit food pantry organization. 

The train will stop at the track crossing on Harwood Ave., near the Little Red Store and Homestead Realty (773 Harwood Ave.). Parking is available at Hart Park. To get from Hart Park to the track crossing, take the footbridge east of the tennis courts. 

The train is expected to arrive at 4PM and depart by 4:45PM (all times are approximate and subject to change depending on when the train arrives). 

December 6: The Village Tree Lighting

Join us in Root Common Park as we light the tree and enjoy holiday carols (5PM), visit with Santa (5:30PM), enjoy mulled wine and hot chocolate from Draft & Vessel, and experience a kids’ scavenger hunt with prizes. 

Then, head to the grand opening of the Wauwatosa Holiday Market in the Harts Mills Parking Lot (the Farmers Market parking lot) at 6:30PM for a traditional keg tapping to “officially” kick off the market. 

December 6 – December 17: Wauwatosa Holiday Market

This year’s first-ever Wauwatosa Holiday Market will be brought to life by outdoor shopping with authentic chalets decorated for the holiday season, as well as the stunning surrounding European-esque architecture and sparkling string lights hanging overhead.

 While walking in the cozy vendor village, market-goers will have the opportunity to buy handmade artisan goods in the open-air market. Enjoy the heated festival tent for live musical holiday entertainment and dance performances for the whole family, as well as traditional German food, beer, and mulled wine. Plus, Santa may make an appearance or two during the market!

Holiday Market Hours

  • Wednesday, December 6th: 3-9PM
  • Thursday, December 7th: 3-9PM
  • Friday, December 8th: 10-10PM
  • Saturday, December 9th: 10-10PM
  • Sunday, December 10th: 10-6PM
  • Monday, December 11th: 3-9PM
  • Tuesday, December 12th: 3-9PM
  • Wednesday, December 13th: 3-9PM
  • Thursday, December 14th: 3-9PM
  • Friday, December 15th: 10-10PM
  • Saturday, December 16th: 10-10PM
  • Sunday, December 17th: 10-6PM

Discover Even More Ways to Shop

Continue your celebration beyond The Village over to our retail hub—Mayfair Mall and the Mayfair Collection — where you’ll find cherished dining and entertainment destinations along with high-end options to round out your holiday shopping experience.


Learn more about where to stay, where to eat, and things to do while you’re here in Wauwatosa.