The City of Pickering would like to present our new event:

Fall Fling

New to Millennium Square
Saturday, October 28
11:30 am – 3:00 pm

Get ready for Fall Fling!

Join the City of Pickering and Nautical Village local businesses for an exciting new event in Millennium Square this Fall. Enjoy the local vendor market, miniature train rides, live music, picturesque autumnal decorations, and giveaways... all along Pickering’s waterfront. Free and fun for all ages. 

October 28

Visit the Destination Pickering tent and select businesses for Community Trick or Treating. Costume dress up is encouraged. 

Costume contests will be held in Millennium Square at the Stage during the intermissions. There will be contests for Dogs, Youth, and Groups.

Judges for the Best in Show Dog Costume Contest will be appointed at random from the audience to avoid spooking the contestants. However, scores for Youth and Group Costumes will be awarded based on audience applause so be sure to bring out your cheer squad.

Millennium Square Stage Schedule
11:30 am: Fiddlestix
12:15 pm: Best in Show – Dog Costume Contest
12:45 pm: Fiddlestix
1:30 pm: Youth Costume Contest
2:00 pm: Fiddlestix
2:45 pm: Group Costume Contest


2023 Fall Fling Map

Vendor Market

Both DatesOctober 21October 28

Maple Grove Farms

The Letter Head

Henna Yasir

Miss Burt's Soap


Bunny’s Burrow Crochet



Sue’s Gnomes

Rouge River Crafts & Candles

Heirloom Heather

The Glitzy Gazelle

My Beading Art

Timber Truck Designs

Pumpkin Patch Creations

L&E Mama Designs 

Dana Sews

Wendy Daly Studio

Entwood Canada

Curry People Candle Co.

Vintage Stitch

Cozy Creations by Araya



The Pop-Up Costume Swap

Holding onto old Halloween costumes you don’t know what to do with? Looking to upgrade your costumes for this year?

The City of Pickering and Pickering Public Library will be hosting the first ever Pop-Up Costume Swap this Halloween season.

Starting Tuesday, October 10, costume donations will be accepted in the Destination Pickering donation bins located in the Central Library lobby and the George Ashe Library lobby.

Here is how to participate in the Swap:

  • Donate clean new or gently used costumes in advance or during designated Swap times
  • Visit one of our Pop-Up locations to browse the costume selection and potentially find your costume for this year

Please note: Availability of costumes, including size, style, and variety, cannot be guaranteed and will vary depending on the Swap date, location, and time. Donations are not required to participate in the Swap.

The designated Swap times are as follows:

Fall Fling – Vendor Market, Millennium Square
Saturday, October 21 from 11:30 am – 3:00 pm
Saturday, October 28 from 11:30 am – 3:00 pm

Pickering Public Library – George Ashe Branch, Quiet Study Room
Tuesday, October 24 from 6:00 pm – 8:00 pm

Pickering Public Library – Central Branch, Children’s Area
Thursday, October 26 from 6:00 pm – 8:00 pm