Main Street Douglas
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Enterprise & Main Street Douglas Events
<p><span class="ql-size-large">Douglas offers events all year long, with exciting opportunities to join the community during the fall and winter months. From Oktoberfest and Haunted History Walking Tours to Haunted Houses, Craft Fairs, and the Fire on Main Street Chili Cook-Off, there’s always something happening. </span></p><p></p><p class="ql-align-center"></p><p class="ql-align-center"><span class="ql-size-large">Explore our full </span><a href="https://www.seewhatconversecando.com/calendar/" rel="noopener noreferrer" target="_blank" class="ql-size-large">event calendar</a><span class="ql-size-large"> for more details on other happenings in Douglas and make plans to participate or attend! </span></p><p class="ql-align-center"></p><p><strong><u>Jan-Sept 2026 events:</u></strong></p><ul><li><strong>Main Street Douglas Spring Cookie Hop</strong>, May 2, 2026</li><li><strong>Park It at the Museum Food Truck Fest</strong>, First Thursday, May 7th &amp; June 4th, 2026</li><li><strong>Douglas Blooms Flower Project-</strong> planting day May 16, 2026</li><li><strong>Knight Kruisers Annual Scholarship Car Show Celebration</strong> June 13, 2026</li><li><strong>Jackalope Days </strong>June 12-14, 2026. Includes:<ul><li><strong>Railroad Day</strong> (Friday@ Railroad Museum) -</li><li><strong>Kids Market </strong>(Friday@ Railroad Day) -</li><li><strong>Ride Row &amp; Run </strong>(Saturday @ WSF) -</li><li><strong>Vendor Fair</strong> (Saturday @ Jackalope Square) -</li><li><strong>Low Rider Dog Races </strong>(Saturday @ Jackalope Square)</li><li><strong>Chalk Fest</strong> (Saturday @ Jackalope Square)</li><li><strong>Knight Kruisers 26th Scholarship Car Show </strong>(Saturday Downtown Douglas)</li><li><strong>LB Street Dance</strong> (Saturday @ LB Bar)</li><li><strong>Community Awards &amp; Block Party</strong> (Sunday @ MHCC) - Be thinking about those nominations!</li><li><strong><em>NEW!</em> LOUD &amp; LOCAL Music Fest</strong>: Details to come</li></ul></li><li><strong>First Responders Freedom Fest: </strong>TBD<ul><li><strong>Firecracker 5K</strong></li><li><strong>Stars &amp; Stripes Kiddie Parade</strong></li><li>Inflatables</li><li>Fun &amp; Games</li><li>Cash Bar</li><li>Food Trucks</li><li>Live Music</li></ul></li><li><strong>Jackalope Square Farmers Markets</strong>, Aug 8, 22, 29, Sept 5 &amp; 12, 2026 - 9a-noon -vendor registration opens July 1</li><li><strong>Wyoming State Fair Parade - Theme: TDB. </strong>Aug 15, 2026, 10 am Entrant registration opens July 1</li><li><strong>Oktoberfest</strong> TBD - vendor &amp; 5K registration open July 1</li><li><strong>Jackalope</strong> <strong>City Scarecrow Contest </strong>in October 2026 Sign-ups open online beginning on September 1. Deadline to enter will be Oct 5th, judging Oct 9-18th with an online passport.</li><li><strong>EBA Skeleton Scavenger Hunt</strong> business registration begins Sept 1, deadline to enter will be Oct 19. Hunting passport will be open Oct 21-Nov 1, 2026.</li><li><strong>Nightmare at the Museum DHS Haunted House</strong> October 24-25, 2025, 7-10pm</li><li><strong>Main Street Douglas Haunted History Walking Tours</strong> in October dates TBD, with special VIP night including a paranormal invesigation</li><li><strong>Cowboy Christmas</strong> Nov 20-22, 2026 </li><li><strong>Fire on Main Street Chili Cook Off </strong>TBD</li><li><strong>Mingle &amp; Jingle</strong> Dec 4-6, 2026<ul><li><strong>Christmas Parade</strong> Dec 4, 2026</li><li><strong>Christmas at the Depot</strong> Nov 28 &amp; Dec 5-6, 2026</li></ul></li><li><strong>Jackalope Junction Christmas Shop </strong>Nov 27-Dec 24, 2026</li></ul><p></p><p class="ql-align-center"><span class="ql-size-large">To be an event sponsor, contact Jen Goodwin at jgoodwin@candowyoming.com or call 307-358-2000 for more details! We appreciate all support to help us host any of our community events listed above.</span></p><p class="ql-align-center"></p><p class="ql-align-center"></p><p></p><p class="ql-align-center"></p>