There's a version of the first weekend in October that most visitors get: drive up for the aspens, take a photo from a pullout, drive home. And there's the version we push our guests toward, which involves a closed main street at 9,500 feet, a pie-eating contest, and a burro getting scratched behind the ears by four hundred strangers. Cripple Creek's Fall Fest lands on Bennett Avenue October 3–4, 2026, according to the city's 2026 event calendar — and it falls in the last stretch of the year that the town's free-roaming donkeys are still out on the street.
That second detail is the one nobody tells you, and it's why we'd pick this weekend over the ones on either side of it.
The donkey clock is real, and it runs out in mid-October
Cripple Creek's donkeys aren't a tourist installation. They're descendants of the burros that worked these gold mines, turned loose when the mines wound down, and looked after ever since by the Two Mile High Club — an all-volunteer outfit that's been at it since 1931 and runs entirely on donations. The herd sits around fifteen animals, a mix of the original line and rescues folded in over the years.
Here's the part that governs your calendar: the donkeys roam free from about mid-May through mid-October, then move to a winter pasture off C Street and Thurlow until spring. Show up on a July afternoon and you'll find one asleep in an intersection. Show up in November and you'll find an empty street and a plaque. Fall Fest on October 3–4 sits just inside that window, and it's the last event of the season built around them — including a donkey braying competition in which humans of all ages attempt their best impression and mostly embarrass themselves.
Local tip: If you want to feed them, buy the approved donkey biscuits sold at the Heritage Center, the jail museum, and shops up and down Bennett — a couple of dollars, and the money goes back into the herd's vet care. Don't bring carrots, apples, granola bars, or anything out of your cooler. The club has run a "Healthy Herd" campaign for years precisely because well-meaning visitors were making the animals sick. And keep small kids in front of you rather than behind: these are stock animals, not petting-zoo props, and a startled donkey moves fast.
What actually happens on Bennett Avenue
Fall Fest is young — this is its third year — but it's grown into a real street festival rather than a card table and a banner. The program on the Two Mile High Club's Fall Fest page lists live music across three stages, pumpkin carving and painting, pumpkin bowling, gold panning, wood carving, a hay treasure hunt, a pet parade, a free kids' zone, hayrides, beer gardens, food vendors, a fall photo booth, and an outdoor movie on Saturday evening.
Last year's edition ran Saturday 10 a.m. to 9 p.m. and Sunday 10 a.m. to 5 p.m., and we'd plan on something close to that shape. The city's calendar carries a blanket "all dates are subject to change" note, so confirm the final schedule a week out rather than driving up on faith.
A practical read on timing: come Saturday if you want the whole thing, bands and evening movie included. Come Sunday if you have young kids or you'd rather not shoulder through a crowd — the street is noticeably calmer, the vendors are all still there, and you're back at the cabin by dinner.
Make it a weekend, not an afternoon
- The Autumn Art Show, September 24 – October 4. Eleven days of regional work at the Cripple Creek Heritage Center, which in recent years has run daily 10 a.m. to 5 p.m. with free admission. Its final weekend is Fall Fest weekend, so you can do both without moving the car.
- The tail end of aspen season. Teller County's aspens usually peak mid-to-late September, which makes the first weekend of October the last of it — thinner canopy, more gold on the ground, far fewer cars on the good roads. Our fall color guide has the drives worth taking on the way up.
- Elk, still. The rut runs into mid-October, and the meadows between Divide and Cripple Creek are the same ones you'll pass on the way to Fall Fest. Go at dusk on the way home — here's where we send people.
- Underground, if the weather turns. The Mollie Kathleen Gold Mine drops you a thousand feet into a real vein and holds about 50°F no matter what's happening on the surface. Best bad-weather backup in the county.
The drive, and two things people get wrong
From our Florissant cabins it's roughly 25 minutes down Highway 67; from Woodland Park, closer to 45. Both routes run through Divide, and there's no gas between Divide and Cripple Creek — fill up before you drop toward town, because the only thing worse than missing the pet parade is hunting for a pump that doesn't exist.
The other one: October at 9,500 feet is not October at home. We've seen 70 and sunny on Bennett Avenue and we've seen four inches of wet snow on the same date. Bring a real jacket and pack it even if Thursday's forecast looks perfect. Street parking fills by late morning on Saturday; the lots at the east end of Bennett turn over faster than people expect, and it's a five-minute walk either way.
Where we'd put you for that weekend
If Fall Fest is the anchor, stay on the Florissant side and keep the drive short. The Surrey Cabin and Highland House both sit inside half an hour of Bennett Avenue, and Highland sleeps eleven, which makes it the one we recommend when two families split a weekend. Our newest place, the Lion House, is on the same side of the county and still flying under most people's radar. And if you're the type to drive home at dusk and then sit outside anyway, the Kingston Stargazing Cabin is built for exactly that — early October brings dark, cold, unusually steady skies.
Woodland Park works too if you want restaurants and a grocery store within walking distance; the Coyote A-Frame trades twenty extra minutes of driving for that convenience.
One honest note on timing: the first weekend of October used to be quiet up here. It isn't anymore. Between the last of the color, the elk, and Fall Fest, it now books about as early as the last two weekends of September do — so if it's on your list, don't wait for the leaves to turn to decide.
Fall Fest weekend, October 3–4
Six cabins, all within 45 minutes of Bennett Avenue. Book direct and save up to 15% vs Airbnb — same cabins, same hosts, no platform fees.
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