Vail Valley Charitable Fund Unveils Undressed Calendar at 30th Anniversary

Aspen —The air in Vail Village usually hums with the low, steady thrum of luxury and commerce, but on September 19, that frequency shifts. It gets louder, warmer, a little more chaotic. You can feel it before you even see the venue, Chasing Rabbits, where the Vail Valley Charitable Fund is pulling back the curtain on its 30th anniversary. If you’ve been wondering how a nonprofit that quietly pays medical bills for neighbors in crisis celebrates three decades of existence, the answer is simple: they take their clothes off. Or rather, they ask others to do it for them.

The Vail Valley Charitable Fund is unveiling its Undressed Calendar at a celebration that promises food, drinks, music, and the first public look at this year’s models. The suspense is real. Since the last calendar was produced in 2016, the community has been left guessing about who might appear on its pages. The identities of participants have always been kept secret until reveal night, a tradition that keeps the mystery alive. Past editions featured names like Trista and Ryan Sutter, Helmut Fricker, Josiah Middaugh, and the 10th Mountain Roller Derby Girls. You never know who is going to be in it, which makes the September 19 reveal worth the drive if you haven’t already made your plans.

Rohn Robbins, the fund’s chairperson and founder, framed the event not as a spectacle for its own sake, but as a community ritual. “We will present the calendar as we have in previous years in good taste, in the spirit of fun and community, and to help lift up our neighbors in their time of need,” Robbins said. He hopes the evening will put a smile on faces while supporting what he calls the “good and meaningful work” the fund has performed over three decades.

That work is substantial. Since 1996, the fund has distributed more than $10 million to over 2,400 community members facing illness or injury. The money helps ease the burden of medical bills and essential living expenses, allowing families to focus on healing rather than financial survival. Brooke Skjonsby, the fund’s executive director, emphasized that this impact isn’t a solo act. “Community support for our events and programs has defined the Vail Valley Charitable Fund for 30 years,” Skjonsby said. She noted that the generosity of businesses, individuals, and grant funders allows the organization to reach more neighbors through its direct aid, dental, physical therapy, and breast cancer programs. For Skjonsby, thirty years of impact is a reflection of an entire community choosing to take care of one another.

The anniversary also marks a deepening of cultural ties in the valley. In 2026, the fund was honored as the inaugural featured community partner of the Bravo! Vail Music Festival. Grant recipients, donors, and partners were welcomed to a shared musical experience, a pairing that feels natural given music’s well-known power to heal. The fund is also announcing an exciting town of Vail mural project, a collaboration with Discover Vail that brings art into the public square.

The Town of Vail’s Art in Public Places program expressed its enthusiasm for this collaboration, noting that local artist Tara Novak created a truly uplifting and vibrant mural for the community to enjoy. If you look closely at the new public art, you can see the same spirit that drives the calendar: a commitment to visibility, to joy, and to the quiet, steady work of showing up for one another.

The calendar reveal happens on Sept. 19 at Chasing Rabbits. The models are still a secret, the music is already planned, and the community is ready to celebrate three decades of showing up.