Outside the racetrack, Sarai led us to our ride—a red Mustang convertible—and suggested we track our first likely suspect using our tablet’s map feature. The Gamble’s tiered pricing structure includes a basic bring-your-own-car option at a lower price point ($825 per person), but we opted for the all-inclusive package ($1,225 each), which includes meals and a flashy ride. A top-tier “Perfecta” package ($3,250 for two) goes further, tailoring specific elements to each traveler. (Too rich? A just-announced “Double Date” option brings the price as low as $560 per person for a group of four.)
Soon we were driving through the wooded byways of the North Bay. Though rainy weather kept the convertible’s top up, the misty landscape added a layer of atmosphere to the experience as we headed toward Nicasio, a charming postage stamp of a town 30 miles north of the Golden Gate Bridge.
I’d driven through Nicasio many times and admired its landmark, a quaint white church, but I’d never stopped to take a closer look. This time, with an iPad-issued audio tour and directive to explore the town for clues, we found ourselves scrutinizing details—the numbered boxes in the tiny post office, a birdhouse hidden in a tree, the creek bed beneath a rustic bridge where, legend had it, an ornery local had tossed the bodies of trespassers. In a juxtaposition of quotidian life and the story’s sometimes sinister underpinnings, we discovered a macabre clue hidden yards from a T-ball game in progress. Carrying the blood-stained evidence back to our car, we wondered what stories people might tell about us, should they be looking closely.
To reveal the rest of our stops could be to spoil the fun of the experience. The story led us through some of Marin’s most charismatic locales and included ample opportunity to cover, slowly and deliberately, ground that we might hurry through had we been visiting on our own. With stretches of time to explore between specific assignments—such as driving to a new destination or meeting with a character—we perused a bookstore, tried on cowboy hats at a tack shop, and lunched on local oysters and champagne. And, of course, we encountered the rest of our story’s main characters in person.
We took a walk with Herb, Talisman’s aw-shucks owner, who unspooled parts of his story under our admittedly amateur cross-examination. Dustin, another character, chatted us up after hitching a ride. Both gamely responded to every question we threw at them, never breaking character, but some queries were quite obviously deflected. Neither seemed entirely trustworthy; both left behind perplexing clues.
“We want to balance giving the travelers agency in terms of how they absorb the narrative and maintaining the integrity of these complex, conflicted characters, all of whom have a little something to hide,” said Bhabha of the actors’ role in unraveling the storyline.
Bhabha likens participation in the Headlands Gamble to being a detective in David Lynch’s Twin Peaks, with its web of small-town eccentrics and intrigues. "Our greatest resource is the environment we're in. We get incredibly high production values for free, just by virtue of being there."
It helps that Marin, known for its monied, liberal residents, is populated with its share of outlandish characters. At times, it was easy to forget who was an actor in our story and who was a civilian playing an extra without their knowledge. In one diminutive church, we met an elderly parishioner who seemed amused, but oddly unsurprised, by our quixotic mission. Local patrons of a local dive bar, the prime gathering place of an insular coastal community, squinted dubiously at us over their beers. A cheerful waitress seemed to know more than she was letting on. How much did these “townspeople” know about us and our adventure, we wondered?
At times, this heightened awareness bordered on paranoia. In town, a man seemed to be watching us from a discreet distance but slipped off when we tried to double back. Once we were convinced we were being tailed. (Bhabha told us of one couple who inquired after Talisman so energetically that one local offered to call the authorities to report the stolen horse.)
We weren’t entirely wrong. Smedresman’s custom technology allowed the stage manager to keep track of our whereabouts as well as that of each actor. They in turn could use their own apps to let the logistics system know that, for example, their scene with us was concluded. The stage manager could also text us from the persona of different characters to check on our progress, and actors shared notes with each other on how we were responding to the experience. If someone wandered way off course, which Smedresman says hasn’t happened yet, the tablet could allow a narrative way to guide them back on track.