The 2026 Vail Comedy Festival was a barrel of laughs with tons of comedy shows, magic and even cinema over Memorial Day Weekend. The second year of FILM@Vail Comedy Festival surpassed all expectations with nearly ten film makers flying in. Vail was alive with laughter and big fun for three crazy days over Memorial Day Weekend. Photography by Jared Chandler.
Headliner Casey Balsham from New York City does her one hour show a few days before the official taping in front of a packed out Sarah’s Lounge in Vail Village.
Founder and organizer of the festival, Mark Masters, hosts the closing show of the festival on Sunday night after thanking community sponsors, staff and pass holders who have attended every year of the festival!
Audience members laugh at a full show held at Manor Vail Lodge. Many of them rep Colorado Avalanche gear to support their playoff run.
A gorgeous weekend full of sunshine and signage promotes the festival to guests of Vail wandering the pedestrian village.
Headliner Tom Thakkar works the audience at a sold out show at Ridge + River.
Headliner Nick Vatterott holds court at a kick off party for comics and VIP pass holders. The event featured food from Vail’s only Michelin rated restaurant (Korean fried chicken sandwich pictured). Thank you Sweet Basil!
Comedian Ty Raney from New Jersey is all smiles at another comedy show during Vail Comedy Festival.
Festival magician Travis Nye delights an audience member at one of several free family friendly outdoor magic shows which were sponsored by Mark Masters Comedy in 2026.
Kids enjoy family friendly magic on the Cucina patio during a beautiful Memorial Day Weekend.
Elyssa Phillips from Los Angeles entertains a daytime audience at another comedy showcase during the festival weekend.
FILM@Vail Comedy Festival returned for a second year. Three feature films and ten short films (pictured: Mashy Potatoes) were screened on a fourteen foot wide movie screen leading to record attendance for the new festival within a festival. Both “ON A STRING” and “BEFORE WE GET STARTED” won golden alpaca awards.
Audience members laugh during a filmmaker Q&A. Festival headliner Tom Thakkar joined surprise guest and star of the film “BEFORE WE GET STARTED”, Ryan Reiss (pictured) to discuss warm up comedy and the film.
Ryan Reiss and Tom Thakkar conduct our first ever in-person Q&A at FILM@Vail Comedy Festival.
Even the dogs are happy at Vail Comedy Festival during a gorgeous late May weekend.
Vail Comedy Festival merch was for sale all weekend long, with one of a kind items featuring your favorite comedy alpaca (not a llama).
Big smiles and laughs from front row audience members at another hilarious comedy show during Vail Comedy Festival.
Festival headliner Robby Slowik from New York City delivers a terrific and hilarious set to a packed out crowd.
Roundabout signs promote Vail Comedy Festival as cars drive into Vail from I-70. Past performers Usama Siddiquee and Leah Bonnema are visible in this photo. Caitlin Peluffo, Derrick Stroup and many other comics grace other poles at Vail’s main roundabouts.
A Vail Comedy Festival banners towers over the iconic covered bridge in Vail Village at dusk as more comedy is about to ramp up.
Audience members enjoy a cocktail and some laughs in the back of a showroom.
Vishnu Akella from Los Angeles is having fun on stage at the 2026 Vail Comedy Festival.
More big laughs from pass holders at the 2026 Vail Comedy Festival.
Festival headliner Nick Vatterott from Los Angeles does a surprise drop in set at a comedy show during the festival.
Surprise drop-in Ryan Reiss from New York City entertains at a comedy show after a screening of his FILM@Vail Comedy Festival selection “BEFORE WE GET STARTED”.
Beers and laughs at Vail Comedy Festival are a perfect combination.
Another intimate comedy show full of smiles at Vail Comedy Festival.
Nathan Loe from Atlanta, GA has the crowd rolling during a show.
Magician Travis Nye astonishes an audience member during a comedy and magic show on stage.
Street magic is a fun tradition that gets guests of Vail who may not even be attending the festival delighted, all the same.
Big laughs at another packed out comedy show during Vail Comedy Festival.
The festival can not happen without an incredible staff, who celebrate the last show of the fest with a quick picture. Thank you 2026 Vail Comedy Festival staff!