Village of Oswego
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2019 Christmas Walk 

Friday, Dec. 6, 2019

5-8:30 p.m. 

The 2019 Oswego Christmas Walk, presented by Allied First Bank, will be held from 5 to 8:30 p.m. on Friday, Dec. 6, throughout downtown Oswego, with your same favorite traditions plus new activities that will make this year even more fun for all ages.

Help Cindy Lou Who usher in the holiday season with a Seussian twist on the traditional tree-lighting ceremony, take a Belgian horse-drawn wagon ride, go skating on the faux ice skating rink, watch an ice sculptor, slide down the giant inflatable sled hill, take a ride on the Toyland train and much more – all for free. Plus, dozens of local Oswego organizations will offer games, crafts, giveaways and prizes and food for sale all night! Bring your wish list and visit Santa at Fox River Academy of Music and Art beginning at 5 p.m. Be in line before 7:45 p.m. to guarantee your visit with the Jolly Old Elf himself -- photos will be taken by Locked In Photography and made available for download following the event. Join in on the fa-la-la-la-ha-ha-ha with improv comedy at the Little White School Museum, and at 8 p.m., make way for the silent, illuminated fire truck parade featuring all your favorite holiday characters down Main Street.

Trolley service

Avoid the congestion of downtown traffic! Trolleys will operate in a continuous loop from Oswego High School to Christmas Walk. Trolley service is available at no charge and will run from 4:00 to 9:30 p.m.

Find fun all weekend long!

The fun continues Saturday morning with Breakfast with Santa, brought to you in partnership with Oswego Foundation for Educational Excellence. Fill up on pancakes, play games, make crafts, and visit with Santa Claus, all benefitting Oswego 308 classrooms, from 8:30 to 11:30 a.m. at Oswego High School. See for more details.

The annual Cookie Walk, brought to you from the Oswego Downtown Association, will also be held from 10 a.m. to 4 p.m. Saturday, Dec. 7, in downtown Oswego. Purchase a tin for $10 in advance at Marmalade Tree, Happenstance Goods and Bentley's Pet Stuff, and go door to door collecting freshly baked cookies from participating downtown shops! Tins go on presale starting Nov 25th. Limited amount of tins available. Must purchase a tin to participate. 

Want to host a booth? 

Businesses and nonprofit organizations are invited to host fun, family-friendly activities in booths on Main Street! Christmas Walk booths are a great opportunity to spread cheer and interact with thousands of engaged Oswego residents.

Applications open Thursday, Sept. 5, for businesses and nonprofits located in the event zone on Main, Jefferson and Van Buren Streets. Applications open to other Oswego businesses on Thursday, Sept. 21. Booth fees are $0 for Oswego-based nonprofits, $50 for Oswego-based businesses, and $75 for businesses and non-profits located outside of Oswego.

The application period for a booth is now closed. 

Thank you to our sponsors!

The 2019 Christmas Walk is supported by generous contributions from: 

  • Allied First Bank Allied First Bank logo
  • Ron Westphal Chevrolet
  • Waubonsee Community College 
  • Herc Rentals, Inc.
  • Shodeen Group
  • Baird & Warner
  • Imperial Service Systems
  • KinderCare
  • Oswego Area Chamber of Commerce 
  • Symphony at the Tillers
  • Country Financial – Sherry Tease Ron Westphal logo
  • Physicians Immediate Care
  • Hennessey’s River View Ford
  • First Place Rental
  • Fox Metro Water Reclamation District
  • Oswego Chiropractic
  • Schoppe Design Associates
  • G.A. BlockerWaubonsee CC logo
  • Meade, Inc.
  • HR Green 
  • MetroNet
  • K. Hovnanian Homes
  • A.Y. McDonald Manufacturing Co.
  • Metropolitan Industries
  • Home Depot
  • Imagination Print and Design
  • Portillo’s
  • Groot

Get all the details

A downloadable 2019 Christmas Walk program and map is available hereand at

Attendees can also get up-to-date information, learn the Christmas Walk shuffle from Christmas Tree Rex and more on the 2019 Oswego Christmas Walk presented by Allied First Bank event page on Facebook.

The 2019 Oswego Christmas Walk, presented by Allied First Bank, will be held from 5 to 8:30 p.m. on Friday, Dec.6, throughout downtown Oswego. 

Still have questions? 

Our elves are happy to answer. Email