"Old Bill's captures the best of who we are as a community." That's how Laurie Andrews, president of the Community Foundation of Jackson Hole, describes a fun run that turns thirty this September. It's a fair line, and also an easy one to say about a town that agrees on almost nothing else. What Andrews doesn't mention is that this year, the run lands on the same Saturday morning as the town's weekly farmers market, and that a week later, the valley's biggest art event will unfold on the exact same six blocks of Town Square where that market sets up its tents.
If you live here, the practical question this September isn't whether to go. It's which Saturday, because the calendar isn't spreading things out. It's stacking two of them directly on top of each other and leaving the third alone.
September 12: The Square and the School Field, Same Morning
Old Bill's Fun Run starts at 8:30am on September 12 at the Jackson Elementary School fields on Willow Street, with staggered starts by category: adaptive 5K and 10K, timed 5K and 10K for adults and youth, and the untimed Fun Run that closes the morning with the Diaper Derby. This is the 30th year of an event that has raised more than $306 million for Teton County nonprofits since its founding in 1997, all of it processed through the Community Foundation of Jackson Hole rather than any single charity, which is part of why the whole town treats it as a shared occasion rather than someone else's fundraiser.
A few blocks away, the Jackson Hole Farmers Market runs its normal Saturday slot on the Town Square, 8am to noon, the same window Old Bill's occupies. Neither event moved to make room for the other. They simply share a morning, and downtown Jackson absorbs both. If you're driving in, free parking for Old Bill's is available at the Home Ranch Welcome Center lot at Cache Street and Gill Avenue, two blocks from the start line, which is worth knowing before you circle the block looking for something closer.
September 19: The Square Does Double Duty
The bigger overlap comes a week later. The 42nd Annual Fall Arts Festival runs September 18 through 20, and its centerpiece, the Jackson Hole QuickDraw & Auction, is scheduled for September 19 from 8am to 1pm on the Jackson Town Square. Thirty artists will create original work in ninety minutes in full view of whoever happens to be standing there, then the completed pieces go straight to a live auction on the spot.
The Farmers Market runs its usual Saturday hours that same morning, on the same square. For a few hours, the space that normally holds tomato stands and cut flowers also holds thirty easels and a running auction. It's the one weekend all year when picking up your produce means walking past a painting being finished in real time.
The timing isn't an accident of scheduling so much as a reflection of how much weight the festival now carries. Jackson Hole was named the number one arts community in the country by Southern Methodist University's Arts Vibrancy Index, released in January 2026 after evaluating more than 900 communities nationwide. That ranking is part of why the auction draws collectors from well outside the valley, and part of why the Saturday before it, September 18, includes a Home Tour of architecturally significant residences from 10am to 4pm, something a smaller arts scene wouldn't attempt. The festival closes Sunday, September 20, with an Art Brunch from 11am to 3pm around town, a lower-key bookend to a weekend that starts loud on the square.
September 26: The Square Alone
Then the compression stops. September 26 is the Farmers Market's last Saturday of the 2026 season, and this time nothing else is scheduled on top of it. No run, no auction, just the market as it's been most Saturdays since June: produce tables, cut flowers, and the crowd that shows up because the food is good, not because something else is happening nearby.
The rest of the valley's outdoor market season closes in the same narrow window. Slow Food in the Tetons wraps its Wednesday People's Market at the Center for the Arts on September 23, and its Farm Stand closes two days after that, on September 25. By the time the Town Square market takes its final Saturday on the 26th, every other outdoor market in town has already gone quiet for the year. It's less a single closing than the whole outdoor food calendar folding up within the same seven days.
Where To Eat Between All Of It
If you're stringing these Saturdays together with dinners in between, two additions to the food scene are worth knowing about, one that's been open long enough to be reliable and one that's brand new this year.
Aurora, the restaurant at the 7,800-foot summit of Snow King Mountain, opened in early 2025 and has settled into being the valley's only dinner reservation that requires a gondola ride instead of a parking spot. General manager Ryan Stanley runs it Thursday through Monday for dinner starting at 4:30pm, with a coffee shop below open 10am to 2pm. Executive Chef Brandon Hicks, whose résumé includes New York's Picholine and San Francisco's The Battery, built a menu around Jackson's foraging traditions, elk tenderloin and buffalo carpaccio alongside yellowfin tuna and swordfish. It's a reasonable answer if you want a view with dinner after a long day on the square.
Newer still is the overhaul at the Jackson Hole Airport. Fine Dining Restaurant Group, the local hospitality company behind Il Villaggio Osteria, launched three new concepts there this past May: Café Bistro, Bar Osta, and Bodega Gourmet Market. Bar Osta draws directly from Il Villaggio's Italian menu, serving breakfast through dinner with both dine-in and grab-and-go options, limoncello berry pancakes in the morning and a diavola grilled cheese by afternoon. If you're picking up out-of-town guests for the Home Tour or the QuickDraw weekend, it's now a genuinely good meal before they've even left the terminal, which wasn't true a year ago.
Picking Your Saturday
None of this is really about doing everything in September. It's about knowing that this year, unlike most, the town's three biggest Saturday rituals aren't evenly spaced. Two of them land on top of the weekly market by coincidence of the calendar, and the third stands alone because everything else has already wrapped for the season.
If you want the run and the market together, that's September 12. If you want to watch an auction next to your produce haul, September 19 is the one weekend all year that happens. And if you'd rather have the square to yourself, one last time before the tents come down for winter, mark September 26 and skip the rest.
Living here means knowing which Saturday is which. If you're thinking about what comes next for your own place in Jackson, whether that's buying, selling, or just understanding what a property near all this activity is actually worth, the Grand Teton Team is a good place to start that conversation.
