Halloween in the Hole: Shadows, Spirits, and Small-Town Spooks

As October deepens in the Tetons, the days grow short and the shadows stretch long across the valley floor. The cottonwoods stand bare now, their branches like bony hands against a slate-gray sky. There’s woodsmoke on the air, frost on the sage, and just enough chill to make you glance over your shoulder. It’s Halloween in Jackson Hole — a time when the mountains seem to whisper and the town transforms into a playground for ghouls, goblins and everyone in between.

Whether you’re seeking a family-friendly fright or a late-night monster mash, there’s something for every spirit this spooky season.

“Clue: On Stage” at the Jackson Hole Playhouse

From October 9 through November 1, the historic Jackson Hole Playhouse transforms into the ultimate murder-mystery mansion with Clue: On Stage. All the familiar suspects —  Scarlet, Colonel Mustard, Professor Plum, and more — come together for a hilarious, fast-paced whodunit where the only thing certain is laughter (and a little mayhem).

With its candlelit interior and crackling energy, the Playhouse is the perfect place to lean into spooky season — no chainsaws or cheap scares, just top-notch entertainment in one of Jackson’s most charming venues. Grab dinner in town, don your finest detective attire and prepare for a delightfully devious night out.

Tickets and info: jhplayhouse.com

Trick-or-Treat on Town Square

On October 31 from 3:30 to 6 p.m., downtown Jackson transforms into a Halloween wonderland. Local businesses around Town Square hand out candy while costumed kids, parents, and pets fill the streets in a parade of creativity and sugar-fueled joy.

It’s the perfect way to celebrate before the evening chill sets in — and before the grown-ups head out for their own spooky soirées. Bundle up, bring a reusable candy bag, and get ready for some small-town magic under the glow of the elk antler arches.

Details: jacksonholechamber.com

Halloween Costume Crawl at the Million Dollar Cowboy Bar and Silver Dollar Bar

When the little trick-or-treaters head home, Jackson’s nightlife takes over. Starting around 7:30 p.m. on October 31, two of the town’s most iconic watering holes—the Million Dollar Cowboy Bar and The Silver Dollar Bar — team up for the annual Halloween Costume Crawl.

Expect live music, drink specials, costume contests and a crowd that knows how to have fun. Cowboy boots and spooky getups are highly encouraged, and the energy is electric. It’s the rowdiest night of the year in downtown Jackson, and the ghosts won’t be the only ones haunting the dance floor.

More info: worthotel.com

The Great Glorietta Halloween Party

For those who prefer their Halloween with a side of sophistication, head to The Great Glorietta Halloween Party at Glorietta Trattoria. Running from 10 p.m. to 2 a.m. on Halloween night, this 21+ bash features DJs, dancing, themed cocktails, and a crowd that takes costumes seriously.

Think gothic glamour meets Italian flair — perfect for anyone who loves a well-crafted cocktail and a little mystery after midnight. Tickets tend to disappear fast, so snag yours early and plan a late-night stroll home under the mountain moon.

Tickets: exploretock.com

Tricks, Treats, and Tetons

Whether you’re wrangling candy-crazed kids or closing down the dance floor, Jackson Hole offers plenty of ways to celebrate the season. The mountains loom like watchful sentinels, the air is crisp and the sense of mischief is alive and well.

So pull on your costume, grab your broomstick — or your barstool — and join the fun. It’s Halloween in the Hole, and the spirits are ready to play.