What is the Kid Boss Market, and how can you attend this Winnipeg holiday market on November 29?

The Kid Boss Market is a free holiday market where young entrepreneurs aged 8 to 14 sell products they've made themselves. It runs Sunday, November 29, 2026, from 10:00 AM to 2:00 PM at Dakota Community Centre, with free photos with Santa. Admission is free, but you'll need to register in advance.

A Winnipeg Holiday Market With a Twist

Most holiday markets are full of seasoned makers and small businesses. This one is different. Every booth at the Kid Boss Market is run by a young entrepreneur who designed their own business, products, pricing, and booth display.

As a Winnipeg REALTOR®, I spend my days helping people make big decisions about their homes and their futures. Hosting this market with my team, Nicole Hacault & Associates, is our way of celebrating that same spark in the next generation of business owners and giving you a fun way to start your holiday shopping close to home.

Event Details at a Glance

What: Kid Boss Market, a holiday market run by young entrepreneurs
When: Sunday, November 29, 2026, 10:00 AM to 2:00 PM
Where: Dakota Community Centre / Jonathan Toews Sportsplex, 1188 Dakota Street, Winnipeg
Cost: Free admission (registration required)
Bonus: Free photos with Santa

What You'll Find at the Market

When you walk through the doors, you'll find booths filled with handmade, one-of-a-kind gifts you won't see in a big-box store. Because every vendor creates their own goods, each table reflects its owner's ideas and creativity.

It's a great chance to:

Find unique gifts for the people on your list
Support kid entrepreneurs in Winnipeg as they make their first real sales
Cheer on young business owners who are learning to pitch, price, and serve customers

For a lot of these vendors, this may be their first time talking to real customers. Your purchase, a kind word, or a question about how they made something can mean a lot.

Free Photos With Santa

Santa is stopping by the Kid Boss Market, and photos with him are free. Photos are first-come, first-served, so plan to arrive early if this is on your list. Bring your camera or phone so you can capture the moment.

Tips Before You Go

A little planning will help you make the most of your visit:

Register in advance. Admission is free, but tickets are required to confirm your attendance.
Bring cash. Some of our young vendors may not have card payment options.
Arrive early. Handmade inventory is limited, and popular items may sell out.
Bring your camera. You'll want to capture your Santa photo.

Why We Host Community Events

Real estate is about more than houses. It's about the communities we live in and the people who make them special. Events like the Kid Boss Market bring neighbours together, support local talent, and remind us what makes Winnipeg such a great place to call home.

My motto has always been "Knowledge is Power!" Whether you're buying, selling, downsizing, relocating, or making a military move, I believe the best decisions come from being informed. Watching young entrepreneurs learn the ropes of running a business is a perfect reflection of that.

The Takeaway

If you're looking for a Winnipeg holiday market with heart, the Kid Boss Market is the place to be on Sunday, November 29. You'll find handmade gifts, support young entrepreneurs aged 8 to 14, and get a free photo with Santa, all at no cost to attend. Just remember to register, bring cash, and arrive early for the best selection.

Reserve Your Free Ticket

Spots are free, but registration is required. Register for the Kid Boss Market on Eventbrite to save your place, and see more of our community events at yourwinnipegrealtor.com/events.

I look forward to seeing you there!

Nicole Hacault, Winnipeg REALTOR® Nicole Hacault & Associates

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