Sheridan Christmas Stroll & Get Caught Shopping
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Sheridan Christmas Stroll & Get Caught Shopping

Sheridan's historic downtown transforms into a festive hub for the annual Christmas Stroll, officially kicking off the holiday season. This beloved event invites shoppers to enjoy in-store specials, wagon rides, marshmallow roasting, and visits with Santa and Mrs. Claus. Purchase a numbered Stroll button for a chance to win prizes and participate in the fun "Get Caught Shopping" promotion.

What to Expect

Numbered Stroll buttons for prize drawings and 'Get Caught Shopping' rewards.

Know Before You Go

  • Tickets: $5
  • Pets: No pets allowed (service animals welcome)

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 🎄 🎄 (5/5)

Best For

Families, shoppers, community members

Vibe

Festive, community-oriented, cheerful

Energy Level

Moderate

Budget

$

Photo Friendly

📷 📷 📷 📷 📷 (4/5)

Weather Sensitivity

Moderate (some outdoor activities)

Special Events & Promotions

  • "Get Caught Shopping" promotion for Stroll button holders
  • Stroll button prize drawings
  • Lighting & Decorating Contest for businesses
  • Free photos with Santa and Mrs. Claus
  • In-store specials and promotions

Tags

holiday marketfamily friendlySanta visitscommunity celebrationholiday shoppingfree eventfestive foodartisanal productsholiday traditionwinter activities

Location

Sheridan Historic Downtown
Main Street
Sheridan, WY
82801

Event Details

Duration

Evening festivities on Stroll day; button activities through Christmas Eve

Ages

All ages

Neighborhood

Historic Downtown

Timed Entry

No

Featured Performers

  • Christmas carolers
  • Musicians

Organizer

Sheridan County Chamber of Commerce

Food & Drink

Free food and beverages, marshmallow roasting

Tips & Advice

  • Purchase your Stroll button early, as they have sold out for the past three years.
  • Check the event's Facebook page for the most up-to-date information on participating businesses and prize winners.
  • Wear your Stroll button throughout the holiday season to maximize your chances of winning prizes and being "caught shopping."
  • Arrive early on Stroll day to enjoy the full range of activities, especially if you plan to get photos with Santa and Mrs. Claus.
  • Consider exploring businesses outside of the immediate downtown area, as many businesses throughout Sheridan County participate.

Frequently Asked Questions

What is a Stroll Button and why should I buy one?

A Stroll Button is a $5, individually numbered button sold by the Chamber and participating businesses. Button holders can win prizes by finding their matching number in a business and can also be rewarded with Chamber Bucks if "caught shopping" by secret elves.

How can I win prizes at the Christmas Stroll?

There are two main ways to win: find the business with the matching number to your Stroll button for a prize of at least $50 value, or get "caught shopping" by a secret elf while wearing your button in a participating store to receive Chamber Bucks.

What are Chamber Bucks?

Chamber Bucks are gift certificates that function like cash at most Sheridan County businesses, helping to keep money circulating within the local community.

What is the "Get Caught Shopping" event?

Starting on Stroll day and continuing on Saturdays through Christmas, secret "elves" look for shoppers wearing their Stroll buttons in participating businesses. If caught, shoppers can be rewarded with Chamber Bucks.

How can businesses participate in the Christmas Stroll?

Businesses can participate by selling Stroll buttons, displaying a matching number for prize drawings, and by being part of the "Get Caught Shopping" initiative. They can also enter the Lighting & Decorating Contest.

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.

Contributors & Updates

Last Updated: Nov 14, 2025
Original Submitter: Sep 17, 2025 The Christmas Events Near Me editorial team

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