Christmas Stroll & Get Caught Shopping
Celebrate Christmas Cheer, Holiday Sales, and More!
Experience the magic of Sheridan’s most beloved holiday tradition
Kick off the holiday season Friday, Nov. 27, at Sheridan’s 31st Annual Christmas Stroll! Enjoy sales and specials, look for your matching Stroll Button numbers and Get Caught Shopping all day throughout Sheridan County! Then from 4 to 8 p.m. join us along Main Street and Grinnell Plaza in Sheridan for evening festivities, including free hay wagon rides; live music and caroling; free hot chocolate, cider, cookies, hot dogs, chili and more; marshmallow roasting; and the fireworks finale at 8 p.m.! Visit with Santa and Mrs. Claus at the WYO Theater from 11 a.m. to 1 p.m. and 4:30 to 7:30 p.m.
Be sure to purchase this year’s Stroll Button for $5 from any participating business or the Chamber office, 54 S. Main St. Buttons go on sale Nov. 2…don’t wait too long to get yours as we have sold out several years!
The 2026 Christmas Stroll is brought to you by the Sheridan County Chamber of Commerce and sponsored by Fremont Toyota of Sheridan, Mountain Mattress Co., Wyoming Corporate Office, Volunteers of America Northern Rockies and Foundation, PDS, Wareing Sheridan Chevrolet, CENTURY 21 BHJ Realty, Frontier Asset Management, Bloedorn Lumber, Carroll’s Furniture, First Northern Bank of Wyoming – Sheridan, Jim & Angie Navarro, Powder River Energy Corp., Powder River Party Rentals, Sheridan Liquor and The UPS Store.
Stroll the Valley | Saturday, Dec. 5
History of Sheridan Christmas Stroll
The Sheridan Christmas Stroll has been held the day after Thanksgiving for the past 30 years and is the official kick off for the Christmas season!
Each year, Christmas Stroll brings 18,000 shoppers to Sheridan. Sheridan’s historic downtown is the hub of the Christmas Stroll event and activities, but businesses throughout Sheridan County participate. Stroll activities include free photos with Santa and Mrs. Claus, wagon rides, marshmallow roasting, in-store specials, Christmas carolers, winning Stroll buttons and much more.
Each year Sheridan County students in Grades 1-6 submit designs for the Stroll button based on the Stroll theme. The winning design is featured on the buttons, and the Chamber and participating businesses sell the Stroll buttons. Starting the night of Stroll, and through Christmas Eve, Stroll button holders can check all participating businesses for the number that matches their Stroll button number. If found, the person with the winning button number receives a prize of at least a $50 value from the business.
Starting on Stroll day and the Saturdays following Stroll, Stroll Button holders can “Get Caught Shopping” locally. Secret “elves” try to “catch” Stroll button wearers shopping in Stroll-participating businesses prior to Christmas. Some lucky shoppers who get caught while wearing their buttons in participating stores may receive up to $200 in Chamber Bucks!
Proceeds from the Christmas Stroll go to the purchase of additional and replacement Christmas decorations for the Sheridan area.
What is a Stroll Button? Is it a crime to Get Caught Shopping?! Christmas Stroll FAQs
What is Christmas Stroll?
The Sheridan Christmas Stroll has been held the day after Thanksgiving since 1996 and is the official kick off for the holiday season. Each year, Stroll brings thousands of shoppers to Sheridan. Sheridan’s historic downtown is the hub of the Christmas Stroll event and activities, but businesses throughout Sheridan County participate. Stroll activities include wagon rides, sales, in-store specials, Christmas carolers and musicians, winning Stroll buttons, free food and beverages, marshmallow roasting, visits with Santa and Mrs. Claus and a fireworks finale. Sheridan’s Main Street and Grinnell Plaza close to vehicles from 4 to 8 p.m. for evening festivities.
What is a Stroll Button?
Each year Sheridan County students in Grades 1-6 submit designs for the Stroll Button based on the Stroll theme. The winning design is featured on the buttons, each individually numbered, and the Chamber and participating businesses sell the Stroll buttons for $5 each. All participating businesses receive a poster with a unique number that matches one of the Stroll Buttons that they post in their business starting on Stroll Day.
Why do people buy Stroll Buttons?
Starting Stroll Day, and through Christmas Eve, Stroll button holders can check all participating businesses for the number that matches their Stroll button number. If found, the person with the winning button number receives a prize of at least a $50 value from the business.
How do people buy Stroll Buttons?
Stroll Buttons are available for $5 each from the Chamber office or Stroll participating businesses starting in early November until sold out. We have sold out of Stroll buttons for the past 3 years. Last year, 3,000 buttons were available and sold.
Are Stroll Buttons only good for one day?
No! In addition to being collector items for many folks, Stroll Buttons should be worn through the entire holiday season. For one, Stroll Button holders have through Christmas Eve to find their matching button number at participating businesses. Secondly, you can “Get Caught Shopping” with your Stroll Button.
Why would I want to get caught shopping?
Starting Stroll Day and every Saturday through Christmas, the Chamber’s secret elves roam Sheridan County looking for folks wearing their Stroll Button while doing business in a Stroll participating business. If you are “caught shopping” by one of our elves, you are rewarded with Chamber Bucks.
What are Chamber Bucks?
Chamber Bucks are gift checks that can be used just like cash at most Sheridan County businesses. They are not only fun to spend, but they also keep dollars in our community.
What is the Lighting & Decorating Contest?
Stroll participating businesses may enter the Stroll Lighting & Decorating Contest at no charge. Businesses decorate based on the Stroll theme for the current year, and the public votes for their favorite via an online poll. The first and second place winners receive Chamber Bucks, a certificate and a ribbon.