Late May in Colorado Springs is one of my favorite times of year, and this weekend is shaping up to be a real gem. The mountains are showing off, the days are long and warm, and the city is buzzing with events for every kind of person and family. From a packed market scene and some outstanding live music to family adventures and iconic Colorado Springs traditions, there is genuinely something for everyone between Friday, May 29 and Sunday, May 31. Let’s get into it.
Vintage Market Days: Life’s a Party
This beloved upscale vintage-inspired market returns to Colorado Springs all three days of the weekend, filling the Norris Penrose Event Center with original art, antiques, clothing, jewelry, handmade treasures, home decor, outdoor furnishings, delicious consumables, and seasonal plantings. It is one of the most popular market events in the Pikes Peak region and draws shoppers from all over Colorado. Friday is an Early Buying Event for first access to the best finds, while Saturday and Sunday open to general admission.
Day/Time: Friday, May 29 through Sunday, May 31 | 10:00 AM – 5:00 PM daily Location: Norris Penrose Event Center, 1045 Lower Gold Camp Rd, Colorado Springs, CO 80905 Price: Check website for pricing (children under 12 free) Link: https://www.vintagemarketdays.com/market/colorado-springs/
Jazz in the Garden: Hennessy 6 (Season Opener)
The beloved Jazz in the Garden series kicks off its 2026 season right here on Friday evening, featuring the Hennessy 6 in the beautiful garden courtyard at Grace and St. Stephen’s Episcopal Church. This ensemble is known for exciting original material spanning multiple jazz styles and flavors with impressive versatility. Bring a picnic, lay out your blanket and lawn chairs, and enjoy live jazz under the Colorado sky. The concert will also be broadcast live on KCME Jazz 93.5 FM.
Day/Time: Friday, May 29 | 7:00 PM Location: Grace and St. Stephen’s Episcopal Church Garden, corner of N. Tejon St and Monument St, Colorado Springs Price: Free admission Link: https://www.gssepiscopal.org/jazz-in-the-garden
Cosmo’s Magic Theater: Random Acts of Magic
For a truly one-of-a-kind Friday evening, head to Cosmo’s Magic Theater for Random Acts of Magic, the show where the audience votes on which effects are performed from a rotating menu of choices. No two shows are ever quite the same, making every performance a fresh experience. Native Coloradan Cosmo Solano performs world-class sleight of hand in an intimate Victorian parlour setting, complete with light desserts and refreshments before the show.
Day/Time: Friday, May 29 | 7:00 PM – 9:00 PM Location: Cosmo’s Magic Theater, Colorado Springs (check website for address) Price: Check website for ticket pricing Link: https://www.cosmosmagictheater.com/
Arthropods! Nature Program for Kids at Fountain Creek Nature Center
Designed for grades K through 2, this hands-on nature program at Fountain Creek Nature Center is a fantastic Friday afternoon adventure for young nature lovers. Kids will learn about insects, spiders, and all sorts of creepy crawly relatives through a puppet show, arthropod activities, and a guided hike to search for real wild arthropods. Pre-registration is required, so be sure to sign up in advance.
Day/Time: Friday, May 29 | 2:00 PM – 4:00 PM Location: Fountain Creek Nature Center, Fountain, CO (just south of Colorado Springs) Price: $4 per person (pre-paid registration required) Link: https://communityservices.elpasoco.com/nature-centers/fountain-creek-nature-center/
Iron Springs Chateau Dinner Melodrama: Yo Ho Ho and a Barrel of Fun
One of the most iconic dining experiences in the Pikes Peak region, Iron Springs Chateau in Manitou Springs is running their hilarious pirate-themed melodrama this weekend. “Yo Ho Ho and a Barrel of Fun” features audience participation, a sing-along intermission, and a Vaudeville-style Broadway musical revue full of comedy, song, and dance. Arrive early to enjoy a three-course dinner before the show begins. This is a classic, family-friendly Colorado Springs tradition that is always a crowd-pleaser.
Day/Time: Friday, May 29 and Saturday, May 30 | Dinner service from 5:45 PM, show at 7:30 PM Location: Iron Springs Chateau, 444 Ruxton Ave, Manitou Springs, CO 80829 Price: Check website for dinner and show pricing Link: http://ironspringschateau.com/
Metcalfe Park Saturday Market: Opening Weekend
Celebrate the opening weekend of the 2026 Metcalfe Park Saturday Market, one of the Springs’ most community-centered outdoor markets. Running every Saturday through September, the market officially kicks off this week at the scenic Metcalfe Park location on Ohio Avenue. Expect local produce, artisan goods, and a relaxed neighborhood atmosphere that makes for a perfect Saturday morning outing. Mark your calendars now through September 26.
Day/Time: Saturday, May 30 | 8:00 AM – 2:00 PM (Opening Weekend) Location: Metcalfe Park, 618 E Ohio Ave, Colorado Springs, CO Price: Free admission Link: https://www.metcalfefm.com/
Black Forest Farmers Market
Head northeast of the city to the Black Forest Farmers Market, one of the largest producer-only markets in the greater Colorado Springs area. With over 70 vendors, every single item at this market is made, baked, or grown by the vendor selling it. Live music from local musicians, a kids corner activity, food trucks, and even SNAP/Colorado Produce Bonus acceptance make this a welcoming community gathering spot every Saturday of the season.
Day/Time: Saturday, May 30 | 9:00 AM – 1:00 PM Location: 6845 Shoup Rd, Colorado Springs, CO (Black Forest area) Price: Free admission Link: https://www.thebackyardmarkets.com/black-forest-market
Pikes Peak International Hill Climb Testing Days
The famous Race to the Clouds is gearing up for its 2026 season, and this weekend marks official testing days on the Pikes Peak mountain road. Competitors will be running the course on both Saturday and Sunday, making for an exciting atmosphere on and around America’s Mountain. Please note that all uphill traffic to the summit will be held until 8:30 AM on both days, though access to Crystal Reservoir remains available. If you are a motorsports fan, this is a great opportunity to feel the excitement building ahead of the full race.
Day/Time: Saturday, May 30 and Sunday, May 31 | Summit road closed to uphill traffic until 8:30 AM Location: Pikes Peak – America’s Mountain, Colorado Springs Price: Check ppihc.org for testing access details Link: https://ppihc.org/
Pecos and The Rooftops at The Whiskey Rose
Texas Red Dirt country fans will not want to miss this one. Pecos and The Rooftops bring their powerful, authentic blend of country and rock to The Whiskey Rose on Saturday night. Known for soulful songwriting and driving live performances, this Texas band has been building a devoted following across the region with hits like “5am” and “Cabin Fever.” This is an 18-and-over show, with guests needing to be 21 or older after 9:00 PM.
Day/Time: Saturday, May 30 | 8:00 PM Location: The Whiskey Rose, 5781 N Academy Blvd, Colorado Springs, CO 80918 Price: Tickets approximately $40 | 18+ (21+ after 9 PM) Link: https://www.thewhiskeyrose.com/
Paddling Film Festival at Colorado College
Hosted by UpaDowna and Colorado College Outdoor Education, the Paddling Film Festival comes to Packard Hall this Saturday evening for a night of stunning outdoor paddling films. Start the night early with the pre-show courtyard gathering where you can grab snacks, enter to win giveaways, and connect with local outdoor nonprofits. Films begin at 6:00 PM with an intermission around 7:00 PM. All proceeds support UpaDowna’s mission of making outdoor adventure accessible to everyone.
Day/Time: Saturday, May 30 | Pre-show courtyard 5:00 PM, Films begin 6:00 PM Location: Colorado College Packard Hall, Colorado Springs Price: Check website for admission (free for CC Gold Card holders) Link: https://www.paddlingfilmfestival.com/
Flying W Ranch Chuckwagon Dinner Show
A true Colorado Springs institution, the Flying W Ranch is now open for its 2026 season and this weekend is a great time to experience their legendary Chuckwagon Dinner Show. Guests arrive early to explore the Western Grounds, with mountain streams, duck-filled ponds, axe throwing, horse and carriage rides, and a narrow gauge train. Then settle in for a hearty cowboy-style barbecue dinner followed by the world-famous Flying W Wranglers delivering a high-energy Western stage show. Shows run Friday, Saturday, and Sunday evenings.
Day/Time: Friday, May 29 through Sunday, May 31 | Shows begin at 5:00 PM (arrive early for grounds) Location: Flying W Ranch, 3330 Chuckwagon Rd, Colorado Springs, CO 80919 Price: General Admission $68 | Seniors and Military $63 | Children (4-12) $33 Link: https://flyingw.com/
Colorado Springs Sunday Market at Acacia Park
Every Sunday from May through October, downtown Colorado Springs comes alive with the Colorado Springs Sunday Market at Acacia Park. Organized by Hunt + Gather, the market brings together farm-fresh food, handcrafted goods, baked goods, and small-batch creations from local makers and growers, with live music and a friendly community atmosphere that is hard to beat. Whether you are a longtime Springs resident or just getting to know the city, this market captures the heart of the local community.
Day/Time: Sunday, May 31 | 9:00 AM – 2:00 PM Location: Acacia Park, 115 E Platte Ave, Downtown Colorado Springs Price: Free admission Link: https://huntandgathercos.com/pages/sunday-market
Kane Brown with Randall King: Navy Federal Jams 2026
Sunday evening at Broadmoor World Arena is going to be electric. Country superstar Kane Brown headlines the Navy Federal Jams 2026 Military Appreciation concert, with special guest Randall King opening the show. This all-ages event is part of a national series honoring military communities, and active military and veterans can receive free tickets through navyfederaljams.com. In addition to the headlining performances, expect food trucks, face painting, a Mission Marketplace with Veteran-owned businesses, and a full family-friendly atmosphere.
Day/Time: Sunday, May 31 | 7:00 PM Location: Broadmoor World Arena, 3185 Venetucci Blvd, Colorado Springs, CO 80906 Price: General Admission $75 | Free for active military and veterans (through navyfederaljams.com) Link: https://www.broadmoorworldarena.com/events/detail/kanebrown
Colorado Springs Fine Arts Center: Current Exhibitions
The Colorado Springs Fine Arts Center at Colorado College is currently showing two outstanding exhibitions this weekend. “Ana Maria Hernando: Cantando Bajito (Singing Softly)” runs through July 3, and “Where I Learned to Look: Art from the Yard” runs through July 25. Both offer rich visual experiences in a stunning historic building in the heart of the city. The FAC is open Saturday and Sunday and is a wonderful cultural stop for locals and visitors alike.
Day/Time: Saturday, May 30 and Sunday, May 31 | 10:00 AM – 5:00 PM Location: Colorado Springs Fine Arts Center at Colorado College, 30 W Dale St, Colorado Springs, CO 80903 Price: $5 – $10 admission Link: https://fac.coloradocollege.edu/
Whatever you choose to do this weekend, I hope it is a great one. Colorado Springs is a remarkable place to live, and weekends like this are a big part of why so many people are making it home. If you or someone you know is thinking about buying or selling in the Pikes Peak region, my team and I are always happy to talk. Reach out anytime at dan@hayespg.com.
