The 2025 Vail Comedy Festival was a barrel of laughs with tons of comedy shows, magic and even cinema over Memorial Day Weekend. The debut of FILM@Vail Comedy Festival was just one special event that highlighted the diversity of entertainment that pass holders enjoyed. Vail was alive with laughter and big fun for three crazy days this May. It will be back May 22-24, 2026. Photography by Jared Chandler.
Headliner Mike E. Winfield from America’s Got Talent (NBC) is all smiles on the largest show of the weekend in a hotel ballroom at Manor Vail.
Organizer and founder of the festival Mark Masters hosts the closing show at the end of a hilarious weekend. The show was held at Ridge + River in Manor Vail.
Show attendees were all smiles during one of many stand-up comedy shows featuring comics from around America and Canada.
Comedy happens in the most unexpected places during Vail Comedy Festival, including at SureFoot the ski boot shop in Vail Village.
Dr. Kevin Fitzgerald is in complete control at a late night pop-up show held at Aviator Nation.
Comics from San Francisco and Los Angeles enjoy some time with a new friend at Christiania Lodge.
Headliner Sarah Tollemache is all smiles in front of a packed house on Saturday night of the festival.
A comedian from Minnesota gets laughs at The Lodge At Vail over Memorial Day Weekend.
Magician Travis Nye wows an outdoor audience at a free kids event in Lionshead outside of the candy store RocketFizz.
Jack Weiler, Mark Masters and Andy Haynes enjoy a back stage hang during one of many comedy shows during the weekend.
Former surprise headliner Derrick Stroup is the focus just one of many new roundabout signs for 2025. Thanks to the Town of Vail for installing the signs which welcomed visitors to Vail as they entered town from highway I-70. The ski mountain, still with some snow is in the background.
Katie Hannigan, Andy Haynes and Sarah Tollemache tape a live podcast episode that can be found on YouTube and on most places where you listen to podcasts. Vail Kicks Ass hat courtesy of DiscoverVail.com
Families are all smiles at another free event for children during Vail Comedy Festival in Lionshead. Kids enjoy candy while they wait for a magic show to start on another gorgeous day over Memorial Day weekend.
Lou Pharis, a Denver based comedian and school teacher, from The Unteachables, gets the crowd going at another pop-up comedy show.
Secret headliner Kevin Shea and Mark Masters behind the curtain, before Kevin heads to entertain a packed out showroom.
Kevin Shea from HBO is hilarious and has the crowd rolling after he is announced as the surprise headliner for the 2025 festival.
FILM@Vail Comedy Festival made its debut in 2025 with a 14 foot wide movie screen and a pop-up movie theater at The Lodge At Vail. “Anxiety Club” (2025) screened to great acclaim with support from local non-profit SpeakUp ReachOut. Director Wendy Lobel joined by video chat after the movie for a Q&A. The film helps destigmatize talking about mental health issues and stars comedians Joe List, Mark Normand, Aparna Nancherla, Baron Vaugh, Marc Maron, Eva Victor and (pictured) Tiffany Jenkins.
Kendall Davond from Atlanta makes one of several appearances during the festival, this one at a late night show at Aviator Nation.
Los Angeles comedian Brandon Vestal entertains a packed room of pass holders during the 2025 festival weekend.
Magician Travis Nye delights an audience of kids of all ages in front of the candy store RocketFizz in Lionshead.
Omaha, Nebraska’s Zach Peterson shares his jokes in a pop-up comedy show at Cucina at The Lodge At Vail.
A banner in Vail Village near Vail’s iconic covered bridge welcomes revelers to town for a weekend full of laughs.
Headliner Andy Haynes on stage during the 2025 Memorial Day Weekend comedy festival event in Vail, CO.
Headliner Katie Hannigan brings the funny in front of sunglasses, record albums and a distinctive lamp at Aviator Nation in Vail Village.
A team of hard working organizers celebrate another successful Vail Comedy Festival. A lot of work, but totally worth it. 2026 here we come …