June is the month Cripple Creek wakes all the way up. The aspens are leafed out, the mountain roads are clear, and the historic mining town packs more events into 30 days than most Colorado towns see in a season. Whether you're driving up from Colorado Springs for the day, planning a weekend at Double Eagle Hotel & Casino, or chasing the Donkey Derby Days crowd, this guide lays out exactly what's happening, when, and how to make a real getaway out of it.
What this post covers:
- The full list of June 2026 events in Cripple Creek
- Jack Dempsey Days at Double Eagle, June 19–21
- Father's Day weekend at the property, including Lombard's Restaurant special
- Weekend giveaways and ongoing Premier Club promotions
- Driving directions, elevation tips, and where to stay
What Events Are Happening in Cripple Creek in June 2026?
June 2026 features seven major events in and around Cripple Creek, including the Cripple Creek Gold Rush Rodeo, Jack Dempsey Days at Double Eagle Hotel & Casino, and Donkey Derby Days. Here is the full lineup:
- Wednesday, June 3 — Shelby Rally, downtown Cripple Creek
- Saturday, June 6 — Pearl DeVere Day, Old Homestead House Museum
- Saturday & Sunday, June 13–14 — Cripple Creek Gold Rush Rodeo, Teller County Fairgrounds
- Sunday, June 14 — Flag Day
- Friday through Sunday, June 19–21 — Jack Dempsey Days, Double Eagle Event Center
- Saturday & Sunday, June 20–21 — Rocky Mountain Mustang Roundup, downtown Cripple Creek
- Sunday, June 21 — Father's Day
- Friday through Sunday, June 26–28 — Donkey Derby Days, downtown Cripple Creek
Three of those weekends double up on events, so book your room early if you're aiming for the back half of the month.
What Is Jack Dempsey Days at Double Eagle Hotel & Casino?
Jack Dempsey Days is a three-day 1920s-themed weekend hosted at Double Eagle Hotel & Casino from June 19 through 21, 2026, celebrating Cripple Creek's gold-rush-era boxing history and the Roaring Twenties.
The centerpiece is the Jack Dempsey Days 1920s Costume Contest on Saturday, June 20. Contestants meet on the Double Eagle Mezzanine in their best Gatsby glamour, flapper flair, or old-school boxing style, then parade over to the Event Center where the contest takes place in the boxing ring. Cash prizes are awarded for the top three:
- 1st place — $500
- 2nd place — $250
- 3rd place — $100
Also on Saturday, June 20, players who earn 100 base points on their Premier Club Card (same day play) can redeem them at the Front Desk for a Double Eagle Lucky Ducky, while supplies last, limit one per player.
Dust off the fringe dress and the pinstripes. This one is a costume weekend worth committing to.
What's Happening at Double Eagle on Father's Day?
Sunday, June 21, 2026, is Father's Day, and Double Eagle Hotel & Casino has two things planned for dads: a free 17-in-1 multi-tool giveaway for Premier Club members, and a steak dinner special at Lombard's Restaurant.
Father's Day Gift Giveaway
From 8 a.m. to midnight on Sunday, June 21, Premier Club members can stop by the Front Desk, show their card, and receive a free 17-in-1 multi-tool. While supplies last, limit one per player.
Lombard's Father's Day Special
Served from noon to 8 p.m., $39.99:
- Juicy T-bone steak
- Baked potato
- Sautéed squash
- Dinner roll
- Slice of cheesecake
Lombard's takes walk-ins, but Father's Day fills up fast. Plan accordingly.
What Saturday and Sunday Promotions Are Running All June?
Every Saturday and Sunday in June 2026, Double Eagle Hotel & Casino runs hourly CasinoPlay giveaways for Premier Club members.
Saturday CasinoPlay Giveaways 5 p.m. to 10 p.m. — Winners chosen electronically. Drawings for $500 in CasinoPlay, once per hour.
Sunday CasinoPlay Giveaways 12 p.m. to 5 p.m. — Winners chosen electronically. Drawings for $250 in CasinoPlay, once per hour.
Mondays, Tuesdays, and Wednesdays in June, Premier Club members earn 2x points on slot play from 8 a.m. to midnight. Thursdays and Fridays, members earn 5x drawing entries for all June CasinoPlay drawings during the same hours. Premier Club Card must be inserted to qualify.
How Far Is Cripple Creek from Colorado Springs?
Cripple Creek is about 45 miles southwest of Colorado Springs and takes roughly one hour to reach via Highway 67. The route is a scenic, winding mountain drive that climbs through Divide and Victor before dropping into Cripple Creek at 9,494 feet of elevation.
A few honest notes for the drive:
- The road is winding. It is paved and well-maintained, but it is mountain driving. Allow extra time if you are not used to it.
- Weather can shift fast. Even in June, an afternoon thunderstorm can roll over Pikes Peak in minutes. Check conditions before you leave.
- Watch for wildlife at dawn and dusk. Deer and elk cross Highway 67 regularly.
From Denver, plan on about a two-hour drive south via I-25 and then west through Colorado Springs.
What Should I Know About the Elevation?
Cripple Creek sits at 9,494 feet on the southwest flank of Pikes Peak, which is high enough that some visitors feel mild altitude effects on day one, especially if they are coming from sea level.
The best advice from people who live here:
- Drink more water than you think you need.
- Go easy on alcohol the first night.
- Pace yourself if you are walking the historic district uphill.
Most visitors feel fine after a day. If you have heart or lung concerns, talk to your doctor before booking.
Where Should I Stay in Cripple Creek in June?
Double Eagle Hotel & Casino is located on Bennett Avenue in the heart of historic downtown Cripple Creek, which puts you within walking distance of the Mustang Roundup, Donkey Derby Days, the Heritage Center, and the rest of the historic district.
The property combines a full hotel, the casino floor, the Double Eagle Event Center (home to Jack Dempsey Days), Lombard's Restaurant, and Prospector's Perk Coffee House under one roof. For Premier Club members, there is also a new everyday Play. Earn. Stay. promotion: earn 250 base points on same-day play and redeem at the Hotel Front Desk for a complimentary standard hotel room that night. Earn 400 base points and you can redeem for a complimentary suite. Based on availability, points must be earned the same day as the hotel stay and redeemed by midnight. Presidential Suites are not included.
For a busy weekend like June 19–21 or June 26–28, book ahead. The town runs full.
Frequently Asked Questions
What is the biggest event in Cripple Creek in June?
Donkey Derby Days, held June 26–28, 2026, is the largest and most well-known event in Cripple Creek each June. It celebrates the town's mining heritage with parades, live music, and the famous burro races down Bennett Avenue. The Cripple Creek Gold Rush Rodeo and Jack Dempsey Days at Double Eagle are also major June draws.
Is Cripple Creek family-friendly?
The town of Cripple Creek is family-friendly, with attractions like the Cripple Creek & Victor Narrow Gauge Railroad, the Cripple Creek Heritage Center, and downtown events that welcome all ages. The casino gaming floor at Double Eagle Hotel & Casino, however, is 21 and older. Families can stay at the hotel and enjoy the restaurants while adults visit the gaming floor.
Do I need a Premier Club Card to attend events at Double Eagle?
A Premier Club Card is free to sign up for at the Premier Club desk and is required to participate in CasinoPlay giveaways, point-based promotions, and the Play. Earn. Stay. hotel promo. Public events like the Jack Dempsey Days Costume Contest are open to anyone, though point-earning perks like the Lucky Ducky giveaway require the card.
Is there a Military Appreciation discount at Double Eagle?
Yes. Active or retired military personnel can present their Military ID and player's card at the Premier Club to receive $5 in free CasinoPlay. The Premier Club desk must activate the reward, and the prize is valid once per day.
What is Lombard's known for?
Lombard's Restaurant at Double Eagle serves an All-American Breakfast all day during open hours, a Saturday Prime Rib Special, and Weekend Wings on Fridays, Saturdays, and Sundays from 4 p.m. to close. The Father's Day T-bone special on Sunday, June 21, is $39.99 and includes a full plate plus cheesecake.
Plan Your June Visit to Cripple Creek
June fills up fast in Cripple Creek. If you are putting together a weekend around the rodeo, Jack Dempsey Days, Father's Day, or Donkey Derby Days, book your room early and give yourself a full day to enjoy the town. Reserve a room at Double Eagle Hotel & Casino at [reservations link] or call the property directly at [phone number]. We will see you in Cripple Creek!