Cheyenne Christmas 2026: An LGBTQ-Welcoming Old West Holiday Getaway Guide

In Cheyenne, even Santa has a ranch. Wyoming’s capital puts its own spin on the season with Old West Holiday, pairing Pony Express wish lists and visits with Santa’s horses with downtown shopping and evenings aboard the Holiday Lights Trolley. Make a weekend of it with locally owned restaurants, drinks with friends and a little room in your suitcase for something Western.

Start your holiday getaway November 28, 2026, when the Cheyenne Christmas Parade brings illuminated floats and Santa’s arrival downtown at 5:30 p.m. Spend the afternoon shopping, catch the parade, then settle in for dinner and an overnight stay. There’s no need to make the drive home the final event of the evening.

For a December escape, plan around December 5, 12 or 19. Spend the day visiting Santa and Mrs. Claus at the Whipple House, meeting Santa’s horses at Kringle Ranch and sending letters by Pony Express at Chronicles Post & Station. After dark, trade the driver’s seat for a warm ride past Cheyenne’s decorated homes aboard a seasonal Holiday Lights Trolley Tour. Friends planning a weekend together can also build their stay around the December 12 Running of the Santas, a 21-and-over festive dash and downtown bar crawl.

Cheyenne’s holiday traditions give travelers a reason to come, while its restaurants, shops and historic downtown give them a reason to stay a little longer. Find holiday happenings at Old West Holiday, explore trolley tours and choose your home for the weekend at Places to Stay.