The Jack Daniel’s tasting is one of those rally traditions that pulls the same faces back every August. Jed Lirette, the brand’s ambassador, runs the whole thing, and by now he’s as much a fixture of Sturgis as the bikes parked down on Main. I usually introduce and host the event myself, and this year I also grabbed a microphone and worked a few tables.

The Regulars Who Never Miss It

Some of these folks have been coming back longer than I have been drinking Jack.

Chris was on his fourth year at the tasting with his group, and when I asked what keeps pulling him back, he kept it simple. “Great music, great food, great company.” His drink of the moment was Jack Blackberry mixed into lemonade, and by the time we talked, his glass was nearly empty. “It’s almost gone,” he said. “As it should be.”

A group from Wisconsin has made it nineteen years straight, no breaks. “It’s a lot of great people getting together and enjoying all the things we love,” one of them told me. “Motorcycles. The riding is amazing out here.” When I pushed back and asked if Wisconsin had good riding too, he agreed, then made his case for South Dakota anyway. “We have great riding, but you have the elevation. A lot of great twisty roads.”

Their favorite pour is a discontinued, maple-finished release called Gold No. 27, and they still have a little tucked away that they savor instead of pour freely.

Then there’s a crew from Gillette, Wyoming, on their twenty-fifth rally in a row. That outlasts a lot of marriages. “Every year we come out here, we meet somebody new, and they feel like they’re our best friends,” one of them said. Their rule for the week is simple: no politics, no arguing, bikes, whiskey, and good company. Most of them are members of the Tennessee Squire Association too, the loyalty club Jack Daniel’s runs for its biggest fans, though not everyone in the group qualifies. One of the Squires has the logo tattooed on. Their current favorite is the Heritage Barrel Proof with the toasted barrel finish. “Ended up being one of the biggest surprises,” he said. “I’m thinking it’s probably my favorite.”

The First-Timers Still Figuring It Out

Not everybody at the table has decades in. Jeremy moved to Rapid City from Aberdeen not long ago and was working his first tasting, one age statement at a time. He’s hunting a bottle of Coy Hill, one of Jack’s rarest releases. “I can’t find one,” he said. “It’s really hard to do.”

Matt has come for five or six years and swears by Gentleman Jack, “so smooth and easy to drink.” When he mentioned trying the Jack Blackberry lemonade, I joked that you could be six drinks into that stuff before you realized you weren’t making it to work the next day. He laughed and agreed. “That’s exactly it,” he said.

What’s Actually in the Glass

Ask a room full of Jack Daniel’s fans what they’re drinking and the answers split about three ways. The old guard sticks with Old No. 7, straight up on ice, because it mixes with anything and never lets them down. The middle crowd leans Gentleman Jack so often it stops being a surprise.

Then there’s the crowd chasing single barrel and barrel proof releases, the ten, twelve, and fourteen year expressions that don’t sit on every shelf. Justin Henrichsen owns The Windsor Block Bar in Rapid City, stocked with more than a thousand bottles, and he says that’s where his regulars land now. “It’s not the Old No. 7 that we’re selling anymore,” he told me. “It’s the single barrel stuff, the barrel proof.” What keeps pulling him back to the brand is the Lincoln County Process, the charcoal mellowing step that shapes the whole flavor. “It knows what it is, and it does it well.”

A Seat Cushion Worth Signing

Tiffany’s been riding to Sturgis since 2014, the year she bought her first bike and rode it out from Omaha herself, no trailer involved. That first ride has turned into a full group trip, gaining new riders every year. “It’s become a whole friendship vacation,” she told me. She and her husband play in a cover band called Grunge Pop that performs at the Loud American. Turns out I work for the same company that books them, Homeslice, and when I mentioned it, Tiffany asked, “Wait, you didn’t recognize me?” I did not. 

Her friend across the table has gotten his biker seat cushion signed by Jack Daniel’s master distillers over the years, current and former. One signature dates back to 2015, when current master distiller Chris Fletcher was still the assistant. “This is my Super Bowl football,” he said.

Every Dime of It

Every penny from the ticket to the tasting funds Sturgis Charities. This year raised $12,500, well over the usual $10,000. Even though tasting through the best Jack Daniel’s has to offer is the reason why the bikers come up the hill, helping the Sturgis community is what makes them feel good heading back down.