What's the single best use of a spare hundred dollars in Jackson right now, if the goal is to make it go as far as possible for the community?
It isn't a tip left at Bin22 or a raffle ticket at the farmers market. Between August 14 and 5 p.m. on September 18, 2026, a designated gift to a local nonprofit through Old Bill's Fun Run gets multiplied by a matching pool before it ever reaches the organization. Give that same hundred dollars in October, or in December during the usual end-of-year giving rush, and it arrives as exactly a hundred dollars. The mechanism is the story here, not the 5K.
The math nobody explains at the starting line
Old Bill's gets talked about as a race because a race is the easy part to picture: a start line on Willow Street, a Diaper Derby, a few hundred people in costumes. But the actual leverage event is financial, and it happens whether or not you own running shoes.
Here's how it worked in 2025, the most recent full season on record. The Community Foundation of Jackson Hole built a match pool of $6,566,744 from Mr. and Mrs. Old Bill, a group of major donors called CoChallengers, and additional contributors known as Friends of the Match. Once the season closed, participating nonprofits received a 74.4 percent matching grant on every designated dollar raised, up to $30,000. That means an organization that brought in $30,000 in direct gifts from its own supporters walked away with an additional $22,310 it would not have seen at any other time of year.
That 74.4 percent isn't a lottery or a first-come, first-served scramble. It's a rate applied evenly once the season's totals are tallied, which means the incentive isn't to rush, it's simply to give inside the window rather than outside it. A resident who waits until Giving Tuesday in December to write the same check is leaving that rate on the table entirely.
As Laurie Andrews, president of the Community Foundation of Jackson Hole, put it:
"Old Bill's captures the best of who we are as a community."
The sentiment is true, but the sentence that actually changes behavior is the one about the 74.4 percent.
What that scale looks like in a town this size
Old Bill's raised $26.1 million in September 2025, a record, up from $23.4 million in 2024. That total came from 25,060 individual gifts made by 4,246 donors, which works out to each donor designating roughly six separate gifts in a single sitting. The platform is built for that: donors pick multiple nonprofits and pay for the whole batch in one transaction, so a household supporting the food pantry, the wildlife foundation, and the search and rescue team ends up counted as three gifts under one name.
Run the other direction and the average designated gift lands just over $1,000. That's not a statement about typical household giving in Jackson so much as a reminder that the total includes everything from a $25 gift at a nonprofit's booth to five-figure commitments from major donors, all funneled through the same matching structure.
The bigger number is participation. One in three households in Jackson give through Old Bill's each year. In a county of roughly 23,000 people, that's not a niche charity event. It functions closer to an annual referendum on which local organizations the valley considers worth funding, and the Chronicle of Philanthropy has noted that the model works because matching grants only apply to nonprofits that already have direct support from their own donors, which is what drives so many organizations to campaign hard during these six weeks rather than waiting.
The two events that aren't the run
Before anyone laces up, there's a Friday morning in mid-August that sets the tone. The 2026 season opened on August 14 with the Old Bill's Giving Season Launch Party and Rubber Ducky Regatta at Russ Garaman Park, where more than 200 rubber ducks, each representing a participating nonprofit, dropped into Flat Creek at 10 a.m. and raced to the finish line with help from Teton County Search and Rescue's Swiftwater Rescue Team. The nonprofits behind the winning ducks receive grant prizes, which makes the event a genuine fundraising mechanism dressed up as a photo opportunity.
Run Day itself falls on Saturday, September 12, starting at 8:30 a.m. at Jackson Elementary School fields on Willow Street. Willow Street and East Deloney Street close to traffic for the morning. The schedule runs in stages: timed adaptive racers go first, then timed adult racers, then timed youth racers, then the untimed Fun Run and walk. The Diaper Derby happens at 10 a.m. on the stage near the start and finish line, race winners are announced at 10:30, and the event wraps by noon.
Free parking is available at the Home Ranch Welcome Center lot at Cache Street and Gill Avenue, two blocks northwest of the field. Handicapped parking is reserved at the Jackson Elementary School lot itself. Timed racers can pick up bibs at the Community Foundation's office at 145 East Snow King Avenue between September 8 and 11, or race morning between 7:30 and 8:30 at the start line arch. Registration is free and stays open until 5 p.m. on September 11. Dogs are welcome if they're leash-trained and comfortable in a crowd, but bikes, skateboards, and other wheeled transport beyond strollers and mobility devices aren't permitted on the course.
Who actually shows up at the Nonprofit Village
Last year's Nonprofit Village on the elementary school field held more than 100 booths, and the mix says something about how the matching structure treats every organization the same regardless of size. The Teton County Search and Rescue Foundation raises about a third of its $1.5 million annual budget through this single event, according to its executive director. Smaller direct-service groups like Climb Wyoming, which helps single mothers find jobs, and One22 Resource Center, which runs rental assistance and a food pantry, set up alongside larger, better-funded organizations such as the Jackson Hole Land Trust and the National Museum of Wildlife Art. The Jackson Hole Wildlife Foundation typically hosts a booth with hands-on conservation activities for kids.
The same 74.4 percent match applies to all of them. A dollar designated to a small food pantry gets exactly the same multiplier as a dollar designated to an institution with tens of millions in assets. That's a deliberate design choice, not an accident of scale.
Thirty years in, and the shirt still matters
2026 marks the 30th anniversary of Old Bill's, and the Community Foundation ran a t-shirt design contest earlier this year to mark it, with submissions open from January 21 through February 20. One winning design became the official 2026 shirt, and a separate winning design from a contest for entrants age 12 and under became the youth shirt. Winning artists received a $500 donation made in their name to a participating nonprofit, and finalists received $100 donations. Shirts have been available since August 14 at the Community Foundation's Snow King Avenue office and will be handed out again on Run Day while supplies last.
It's worth keeping the Community Foundation's own finances separate from the annual Old Bill's pool. The Foundation manages more than $205 million in assets across its long-term funds, which is a different figure entirely from the roughly $6.5 million match pool it assembles each year specifically for this campaign. One is an endowment. The other is a seasonal multiplier that exists for six weeks and then resets.
What this actually means if you live here
If you're the kind of resident who gives to local causes anyway, the only decision that changes anything is timing. A gift made between now and 5 p.m. on September 18 gets the 2026 match rate applied to it. The same gift made in November doesn't. Given that the event has generated $306 million for Teton County nonprofits since 1997, and that a third of local households already participate, the smarter move for anyone still deciding when to give this year is simple: do it now, or plan to be at Jackson Elementary School fields on September 12 to see where it goes.
At Budge Kelley Realty Group, we've watched Old Bill's shape this valley's nonprofit landscape for longer than most of our clients have owned homes here. It's one of the clearest windows into how Jackson actually takes care of itself. Whether you're settled in or still getting to know the community, it's worth seeing firsthand. Browse Homes with us anytime, and we'll be at the finish line cheering everyone on.
