Checking in with Downtown

January 24, 2024 | Part 2: The Return of Hamilton Winterfest

Mark your calendars, Hamilton Winterfest returns next week!

This multi-disciplinary festival has become a community staple during the winter months, with multiple events throughout the city that are sure to brighten up these cold and dreary days. Throughout the entirety of the festival you will be able to enjoy concerts and crafts, drag and dancing, theatre, fashion, art installations, and more. This year the festival runs from February 2 to 19.

The first part of Winterfest available for you to enjoy is Winterfest POP, a 10,000 square foot celebration of all things pop culture that is sure to impress. It will transform Jackson Square into a nostalgic paradise, effortlessly transporting you back to your childhood through a series of interactive exhibitions. Running from February 2 to 19, the exhibitions include:

  • Plush: 300+ plush toys from a variety of collectors
  • Action Jackson: 200+ Vintage and modern action figures
  • Retro Rec Room: A series of vintage televisions playing your favourite shows from the 70s, 80s and 90s
  • Scratch N’ Shiff: Giant murals made of retro scratch n’ sniff stickers
  • And much more!

This event is ticketed, and admission prices range from $10-$20. Admission gets you access to the full exhibition, all pinball and video games set to free play, a 6-hole mini put course, 1 slice of ROMA pizza, 1 cotton candy, and 1 hot chocolate. The all-ages times run from 5 to 9 pm Tuesday through Friday, 10 am to 9 pm Saturday and Sunday, and 10 am to 6 pm on Family Day. POP After Dark is 19+ only and runs from 9 pm to midnight Tuesday through Sunday.  You can purchase tickets here.

The fun doesn’t end there, as Winterfest will also be taking over the top of Jackson Square with the Winterfest HUB. This will activate the rooftop plaza of Jackson Square, with a series of free events that are sure to be fun for the whole family. The Winterfest HUB runs from February 9 to 19, and you can enjoy a variety of free events such as:

  • Video installations
  • Sculptural installations
  • Live concerts
  • FROST QUEENS: A Winter Drag Performance
  • And more!

In addition to these activations, the Winterfest HUB will also be home to two exciting events. Love in Lights will take place on February 14 from 6 to 10 pm. This Valentine’s Day event gives attendees the ability to celebrate love alongside light installations, a live DJ, dessert, an onsite photographer, and an LED light-up surprise. You can purchase tickets for this event here. For a more family-friendly event, the Winterfest HUB will also be hosting a Family Day Extravaganza on February 19 from 10 am to 5 pm, in collaboration with the Art Gallery of Hamilton and the Hamilton Public Library. At The HUB families can enjoy live music all day, interactive art and craft-making stations, and more, while the AGH will have a community art project, an Indigenous beading workshop, and more.

If you cannot make it down to Jackson Square, don’t fret! There are a variety of community events scattered throughout the city, so you can still enjoy the winter festivities in a way that better accommodates your schedule. The Community Events Calendar includes:

  • North Central/ Keith Hub FREE Pancake Breakfast on February 10
  • Sewing/Sowing Change: Create your own banner with Styo Starr, Kate Jackson and Greg Smith on February 17
  • gritLIT Open Mic: Fiction on February 2
  • And much more!


Hamilton Winterfest is an amazing opportunity nestled within our coldest months, acting as a celebration of all things art and winter within the heart of downtown Hamilton. Attending Hamilton Winterfest will give you the opportunity to experience some amazing art, exhibitions, and shows from a variety of talented local artists. Make sure you take time to visit Jackson Square or one of the community events throughout the city to experience everything that Winterfest has to offer! You can find more information about all of the Winterfest events through their website here, and then follow them on Facebook, Instagram, X, and TikTok.

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The Downtown Update is the e-newsletter sent by the Downtown Hamilton Business Improvement Area to keep both members of the BIA and interested supporters of Downtown up-to-date with activities and issues in the core of our community.