Douglas offers events all year long, with exciting opportunities to join the community during the Summer, 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.

Explore our full event calendar for more details on other happenings in Douglas and make plans to participate or attend!

July-Dec 2026 events:

• 250th Stars Stripes & Storefronts contest: Business sign up by June 25th. Online passports for judging open July 1-Aug 7th
• 250th celebration in Douglas: July 4, 2026
  • Douglas Volunteer Fire Department Pancake Breakfast 8a-10a, Fire Training Facility on N 2nd Street
  • First Responders Freedom Fest Fun Run 5K registeration/check in 8:30am, race starts at 9am at Washington Park.
  • Freedom Fest Patriotic Kiddie Parade registration/check in at 10 am, line up startsa t 10:3am at the entrance to City Pool on Center Street
  • Freedom Fest in Washington Park until 1pm includes:
    • Inflatables
    • Fun & Games
    • Food Trucks
  • Free Swim Day at the Pool brought to you by The City of Douglas 12-5pm
  • Live Music & Street Dance brought to you by the City of Douglas & the LaBonte Hotel on Walnut Street, 6p-9p
• Jackalope Square Farmers Markets, Aug 8, 22, 29, Sept 5 & 12, 2026 - 9a-noon -vendor registration opens July 1
• Wyoming State Fair Parade - Theme: 250 Years of Trailblazing from Independence to Equality State. Aug 15, 2026, 10 am Entrant registration opens July 1
• Oktoberfest, October 3rd - vendor & 5K registration open July 1
• Jackalope City Scarecrow Contest 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.
• EBA Skeleton Scavenger Hunt business registration begins Sept 1, deadline to enter will be Oct 19. Hunting passport will be open Oct 21-Nov 1, 2026.
• Nightmare at the Museum DHS Haunted House October 23-24, 2026, 7-10 pm
• Main Street Douglas Haunted History Walking Tours in October dates TBD, with a special VIP night including a paranormal investigation
• Cowboy Christmas Nov 20-21, 2026 *Chili Cook Off has moved to Feburary 2027 (see below)
• Mingle & Jingle Dec 4-6, 2026
  • Christmas Parade Dec 4, 2026
  • Christmas at the Depot Nov 28 & Dec 5-6, 2026
• Jackalope Junction Christmas Shop Nov 27-Dec 24, 2026
• Fire on Main Street Chili Cook Off at WSF Feb 20, 2027

Past Events for 2026:

• Main Street Douglas Spring Cookie Hop, May 2, 2026
• Park It at the Museum Food Truck Fest, First Thursday, May 7th & June 4th, 2026
• Douglas Blooms Flower Project- planting day May 16, 2026
• Knight Kruisers Annual Scholarship Car Show Celebration June 13, 2026
• Jackalope Days June 12-14, 2026. Includes:
  • Railroad Day (Friday@ Railroad Museum) -
  • Kids Market (Friday@ Railroad Day) -
  • Ride Row & Run (Saturday @ WSF) -
  • Vendor Fair (Saturday @ Jackalope Square) -
  • Low Rider Dog Races (Saturday @ Jackalope Square)
  • Chalk Fest (Saturday @ Jackalope Square)
  • Knight Kruisers 26th Scholarship Car Show (Saturday Downtown Douglas)
  • LB Street Dance (Saturday @ LB Bar)
  • Community Awards & Block Party (Sunday @ MHCC) - Be thinking about those nominations!

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.