Heather's Pretty Parties

10/12/2026

Year Six✨

As the storm raged on and Frozen hit peak popularity, Tiana and Moana joined the lineup!

Year six also brought us Katelyn — she started as a performer, became our photographer (a massive upgrade, though I still over-edited 😄), and even built us a new website. She’s still with us today, facepainting and photographing, and her skills have only grown. 📸

I’d hired my first assistant at the end of year five, right before Oliver was born, so this was our first full year with that support — one of the best decisions I’ve ever made in this business. ❤️

10/12/2026

Year Five ✨ Let’s Go!

This was the year everything got bigger — including me! I gathered the team for a photo shoot in the living room of my old house, and that’s where I told everyone I was pregnant. Such a fun moment.

I spent most of year five pregnant, which meant lots of creative pregnancy costumes while I accompanied our performers to parties. Face painting was still my main contribution — and by now we were BUSY. Two years of doing this full time, and the weekdays were packed with school visits, daycares, and more. Growing demand meant growing the team.

One of my favourite milestones: our first male entertainer joined the team! We didn’t have superheroes yet, but we were so happy to have him.

And Christmastime brought something extra special — my mom started joining as Mrs. Claus, so some of my son’s very first Christmas photos are with both his grandma AND grandpa as Mrs. Claus and Santa. My heart. ❤️

It’s getting harder to pick photos for these posts because there are just SO many now — and let’s just say my photo editing was... enthusiastic. I was having fun! 😄

10/10/2026

Year Four ✨
Year four was when everything really started to change. Frozen was the biggest thing in the world, and we were hiring more and more people just to keep up with the demand — the business was growing in every direction. I couldn’t do it on my own anymore, or even with just my sisters and friends pitching in.

This was also the year face painting really started to become a focus for me. I spent so much time practising, wanting to develop my skills in that area.

Early that year we held our Frozen Family Fun Day — three sold-out shows, 75+ people at each, a massive crowd and a very long day.

That year I also performed at the Red River Ex for the first time — and met the fantastic Splash’N Boots!

It was a huge year in my life too — I was getting married! In honour of the upcoming wedding, we threw a fake wedding ceremony with Cinderella and Prince Charming, and it was such a fun day with a whole group of princes and princesses, including Darren (who is performing in Cyrano de Bergerac at MTC right now, go see it!!)

And then in 2014, we got married for real — with princesses at our actual wedding. The kids in attendance thought it was the coolest thing, and it meant the world to me.

This year was also when our most senior performer, Emma, started with HPP — in her own homemade Elsa dress! She has grown in every way since then, and she’s still with us today.

You also might start to spot some familiar faces in these photos — a number of our little fans from those early years have grown up and come to work for HPP. They felt the magic as kids, and now they get to create it for others. Full circle. 💙

10/09/2026

Year Three ✨

Continuing our walk down memory lane…

By year three, Tinkerbelle was taking the field — literally! From living rooms to performing in front of a whole stadium, we were learning that magic belongs everywhere.

And then, near the end of year three, the Queen of Snow made her appearance — and changed everything going forward. ❄️

13 more years of memories to come. Stay tuned 💕

10/08/2026

Year Two ✨

Continuing our walk down memory lane…

Two years in, we were still so tiny — just me, a gown, a dream, and a whole lot of heart.

14 more years of memories to come. Stay tuned 💕

10/07/2026

✨ Let’s take a trip down memory lane! ✨
With our 16th anniversary just 16 days away, I’m going to be sharing old photos from each year leading up to the big day! 📸⏳

I can’t believe how fast the time has gone. Stay tuned for Year 2 tomorrow! 🩵

🎉 P.S. To celebrate our anniversary, we will be hosting a special Sweet 16 contest on the big day! Make sure to stay tuned for more details!

10/06/2026

Pictured: me at 16, with my face painted by my mom. And this month, Heather’s Pretty Parties turns 16 too.

Honestly? I don’t think 16-year-old me ever pictured herself running a business like this. But looking back, all the pieces were there — I always loved acting and singing and being with kids. (Clearly the face paint was an early sign too 😄) And when I started this work, it felt like I had found my calling.

Sixteen years of birthdays, giggles, glitter, and magic. And here’s what those years have taught me: no matter how much experience you have, there are always new challenges, new ideas to dream up, and new ways to learn and grow. This business keeps me on my toes but I wouldn’t have it any other way.

Also I’m planning something special for our anniversary, so stay tuned… 👀

Mostly, I just want to say thank you. I’m so grateful for all the support this community has shown us over the years. So many of you started as clients and became genuine friends, and that means the world to me. 💕

And since it’s been a while — hi, I’m Heather! I’m the owner and founder of Heather’s Pretty Parties. For 16 years we’ve been bringing the magic to birthdays and events across Winnipeg with our characters, face painting, and all the sparkle in between. I’m a mom, a business owner, and someone who truly believes every kid deserves to feel special on their big day.

Here’s to 16 years — and everything still to come. 🥂

10/06/2026

10/04/2026

Pumpkins After Dark transforms an evening out into a memorable Halloween experience. Explore illuminated pumpkin displays, enjoy live entertainment and pumpkin carving demonstrations, indulge in seasonal treats, and capture incredible photos along the way. Perfect for families, friends, and Halloween lovers of all ages.

10/04/2026

Bibbidi-bobbidi-BOO! 🪄 Pumpkins are taking over Princess Club just in time for Thanksgiving! 🍂✨
Little dreamers will get to design their dream Cinderella pumpkin—choose between a dazzling, sparkly carriage-blue 🩵 or a classic golden pumpkin from the garden 🧡.
Bring your best dancing shoes, because we’ll also be singing along to royal favorites and showing off our sweetest ballroom twirls! 💃🎶

👑 Wednesday or Thursday sessions available
👑 Drop-ins & full-year registrations open now

✨ Reserve your magic at the link in bio: heathersprettyparties.com/princess-club