November 13th - December 24th, 2026

Shop Downtown & Win BIG with the Holiday Shopping Passport

Get your holiday shopping done in downtown Kingston and win big prizes along the way with the Holiday Shopping Passport! Have fun and support local downtown businesses by bringing your passport with you on your next holiday shopping spree. 

All you have to do is shop downtown! 

Submit Here

How it Works.

Step One:

Shop!

Grab your passport at any participating business and start shopping!

Make a purchase of $10 or more at participating businesses to receive a special holiday sticker to fill your passport!

1 sticker per purchase.
Find list of participating businesses below.

Step Two:

Submit!

Fill your passport with 5 stickers to enter our Holiday Passport draws!

You can drop off your completed passport at a participating business, or take a picture of your passport, and submit online! 

Make sure to submit your Holiday Shopping Passport by December 24th!

submit here

Step Three:

Win!

Every passport you submit could win!  Complete as many passports as you like!  

You could win 1 of 4 weekly draws for $500 in Gift Certificates to Downtown Businesses, OR 
 
Our Grand Prize: 
$3000 in Gift Certificates to Downtown Businesses!

Winners will be contacted via email. 
A vibrant red trolley with Kingston Trolley Tours written on the side stands in front of a beautifully adorned Christmas tree, evoking a cheerful holiday atmosphere.

Free Holiday Shopping Shuttle

Shop in style and catch the Trolley’s special Holiday Shopping Shuttle! Just collect one Passport sticker to hop aboard (kids 12 and under ride free).

Enjoy free rides on:

  • Nov. 13 | 5:00 PM – 8:00 PM
  • Dec. 5 | 11:00 AM – 3:00 PM
  • Dec. 12 | 11:00 AM – 3:00 PM
  • Dec. 19 | 11:00 AM – 3:00 PM

* Please note this does not apply to any Kingston Trolley Tours

Particpating Locations