Pikes Peak Region Events
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Dates: Throughout the holiday season!
Location: Small businesses throughout the region
Forget the big-box stores. Find one-of-a-kind gifts from local shops and artisans – from handcrafted treasures to local flavors, we’ve curated a list of unique gifts from our attractions.
Regional event calendar
There’s always something happening in the Pikes Peak region. From festivals and live performances to family-friendly fun, our friends at Peak Radar keep track of it all. Explore what’s coming up on their community events calendar.
Events for May 2026
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America 250/Colorado 150: Seeing History in Place
May 16 - Sep 26
Sat, May 16 @ 9:30 am
Sat, May 30 @ 2:00 pm
Sat, Jun 20 @ 2:00 pm
Sat, Jun 27 @ 9:30 am
Sat, Jul 18 @ 9:30 am
Sat, Jul 25 @ 2:00 pm
Sat, Aug 8 @ 9:30 am
...
Early Bird Hike & Bike
May 20 - Aug 26
Wed, May 20 @ 5:00 am
Wed, Jun 24 @ 5:00 am
Wed, Jul 29 @ 5:00 am
Wed, Aug 26 @ 5:00 am
Thu, May 21 @ 9:00 am
Thu, May 21 @ 10:30 am
Fri, May 22 @ 5:00 pm
Sat, May 23 @ 5:00 pm
World Olympic Collectors' Fair 2026
May 22 - May 24
Fri, May 22 @ 10:00 am
Sat, May 23 @ 10:00 am
Sun, May 24 @ 10:00 am
17th Annual MeadowGrass Music Festival
May 22 - May 25
Fri, May 22 @ 12:00 am
Sat, May 23 @ 12:00 am
Sun, May 24 @ 12:00 am
Memorial Day Art Show & Sale
May 22 - May 25
Fri, May 22 @ 10:00 am
Sat, May 23 @ 10:00 am
Sun, May 24 @ 10:00 am
Mon, May 25 @ 10:00 am
The Famous Flying W Chuckwagon Dinner Show
May 22 - Oct 17
Fri, May 22 @ 5:00 pm
Sat, May 23 @ 5:00 pm
Sun, May 24 @ 5:00 pm
Wed, May 27 @ 5:00 pm
Thu, May 28 @ 5:00 pm
Fri, May 29 @ 5:00 pm
Sat, May 30 @ 5:00 pm
...
May 16, 2026 - Sep 26, 2026
America 250/Colorado 150: Seeing History in Place
Presented by Colorado Springs Pioneers Museum at The Mining Exchange Hotel Colorado Springs, CO
Join the CSPM to critically reflect on the meaning of and connections to the commemoration of the America 250/Colorado 150 anniversaries. In 2026, how can we make sense of the 250 years since the Declaration of Independence, and 150 years of Colorado statehood? Join a knowledgeable guide on this 90-minute walking tour, exploring how we have marked time throughout the history of Colorado Springs. Consider different regional anniversaries through the built environment and reflect on your own memories and observations of important events and dates. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 17, 2026
'Better Together'
Presented by Colorado Springs Youth Choir at First Congregational Church Colorado Springs, CO
This concert will feature local choirs from across the Pikes Peak region including Good Treble and Mountainside Elementary. Select members of Choral Song and Colorado Springs Youth Symphony will also be featured. We are happy to announce that we will also collab with local visual artist Erin Kittelson for this concert. Her work will be featured in our program and will be on display. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 17, 2026
Open Mic - Recovery Edition
Presented by CaitSpace Ltd at Bittersweet Coffee and Venue Colorado Springs, CO
Join us for a powerful evening of expression, connection, and healing at our Recovery Open Mic. This space is rooted in supporting recovery in all forms, everyone is welcome, exactly as they are. Whether you're healing, growing, celebrating, or simply showing up, this is a space for your voice. All acts welcome: music, poetry, comedy, storytelling, magic, or anything your creativity calls you to share. Free to attend! Free to perform! Come share your story, your art, your truth—or just come listen and be part of a supportive, uplifting community. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 17, 2026
Pollinators in the Park
Presented by City of Colorado Springs Parks, Recreation & Cultural Services at Garden of the Gods Visitor and Nature Center Colorado Springs, CO
Join Park Guide Asya to learn about the vital role bees, butterflies, bats and other pollinating species play in the Garden of the Gods ecosystems. This presentation introduces the diversity of pollinators found in the park, explains how they support plant reproduction and biodiversity, and highlights the challenges they face and how you can help protect them! This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 20, 2026 - Aug 26, 2026
Early Bird Hike & Bike
Presented by City of Colorado Springs Parks, Recreation & Cultural Services at Garden of the Gods Visitor and Nature Center Colorado Springs, CO
All normal park rules will be enforced. For safety and per normal park rules, skateboarding and longboards are not allowed. As always, entrance to the park is free. Free Parking. Parking is available at Parking Lot #1, near the park’s main entrance on 30th Street. Additional and accessible parking available at the Garden of the Gods Visitor and Nature Center as well as the Trading Post. Weather dependent. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 21, 2026
Little Learners: Pikes Peak Wonders Series
Presented by Colorado Springs Pioneers Museum at Colorado Springs Pioneers Museum Colorado Springs, CO
Who doesn’t love a birthday party? This year, Colorado is turning 150, and America is turning 250! The Little Learners: Pikes Peak Wonders Series is for children (ages 3-5) and their favorite grownup. Learn and celebrate the whole year through games, crafts, songs, and history challenges. These programs are designed to help young learners discover and practice essential development skills, all while exploring history! This month we'll dive into the Colorado Early Learning & Development Guidelines for Physical Development & Health and explore movement, navigation, and balance. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026
Little Ranger Walk
Presented by City of Colorado Springs Parks, Recreation & Cultural Services at Garden of the Gods Visitor and Nature Center Colorado Springs, CO
Bring your “nature eyes” and explore Garden of the Gods! Join Park Guide and Junior Ranger co-author Jennifer for this family and stroller friendly walk. Families will leisurely walk into the Park from the Visitor and Nature Center, playing ‘I spy’ or Nature Bingo. Sticker packet included! Sunscreen, sturdy shoes and water recommended. If there is inclement weather, the program will move indoors. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026 - May 23, 2026
Opening Weekend of the Chuckwagon Dinner and Original Western Stage Show
Presented by Flying W Ranch at Flying W Ranch Colorado Springs, CO
Kick off the summer in the best way possible with an unforgettable night on the Ranch full of Colorado Springs beauty, engaging activities, impressive Ranch animals, hearty Cowboy BBQ, and live western entertainment by the world-famous Flying W Wranglers. A special 150/250 homage to our State's and Nation's birthday will be a part of the show! Be a part of the magic of opening weekend and among the first to experience what everyone will be talking about this summer! This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026 - May 24, 2026
World Olympic Collectors' Fair 2026
Presented by Association Internationale Collectors Olympique at Antlers Hotel Colorado Springs, CO
The World Olympic Collectors' Fair is sponsored by the Olympin Collectors' Club, Sports Philatelists International, and the Association of International Olympic Collectors. This event is officially sanctioned and supported by the International Olympic Committee (IOC) and the U.S. Olympic & Paralympic Committee (USOPC). The 2025 Fair was held in Prague, Czech Republic. This promises to be the largest Olympic Collectors Fair in the U.S. in many years, and is part of the build-up for the 2028 Olympic Games in Los Angeles. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026 - May 25, 2026
17th Annual MeadowGrass Music Festival
Presented by Rocky Mountain Highway Music Collaborative at La Foret Conference & Retreat Center 0, CO
MeadowGrass Music Festival is the premiere music festival to kick off summer in the Pikes Peak region. Always held over Friday, Saturday and Sunday of Memorial Day Weekend. MeadowGrass is known for attracting up-and-coming talent from the region and all over the world. Set in a stunning outdoor setting, this family-friendly weekend features live music, local food and craft brews, yoga, hikes, and workshops. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026 - May 25, 2026
Memorial Day Art Show & Sale
Presented by Cripple Creek Heritage Center at Cripple Creek Heritage Center Cripple Creek, CO
All local artist representing acrylic painting, pen and ink, watercolors, photography, metal art and jewelry. All work is for purchase. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
May 22, 2026 - Oct 17, 2026
The Famous Flying W Chuckwagon Dinner Show
Presented by Flying W Ranch at Flying W Ranch Colorado Springs, CO
For over 70 years, the Flying W Ranch has been welcoming guests of all ages to Colorado Springs’ only Chuckwagon Dinner Show—a Western tradition unlike anything else in the region. Loosen your belt and fill up your tin plate with a hearty cowboy-style barbecue dinner with all the fixins’ – served the classic chuckwagon way. Then get ready for a lively evening of stirring Western music and humorous tall tales from the Flying W Wranglers, the second-oldest Western band in the world. The show this year features a special 150/250 celebration of our State's and Nation's birthday. Arrive early to explore the Western Grounds, meet our friendly ranch animals, try your hand at roping and other cowboy skills, do some shopping, and see vibrant demonstrations by Osage Nation dancers. It’s a night of food, music, and frontier charm your family will never forget. This calendar listing is brought to you by Peak Radar, the Pikes Peak region's one-stop, online website for arts and entertainment events, powered by the Cultural Office of the Pikes Peak Region.
