A lot has changed along America’s most famous cinematic drinking route.
I was at the Fess Parker Winery in Los Olivos, California, and I had the urge to drink from a spit bucket. I was hoping to pay tribute to Miles and Jack, the protagonists in the classic 2004 wine-country road trip film Sideways.
In a climactic scene, Miles, played by Paul Giamatti, has just learned that his novel won’t be published. Thwarted when a wine pourer in the tasting room of Fess Parker (disguised in the film under the name Frass Canyon) refuses to over-serve him, he grabs the spit bucket and chugs from it, pouring the whole thing down the front of his shirt.
But I didn’t see any such vessel, which is probably a good thing. And that wasn’t the only difference between the Fess Parker Winery of 2024 and the 2004 version.
Twenty years ago, the tasting room was depicted as an overwrought, hectic tourist trap. Nowadays, it has been transformed into a generous, elegant space made of dark stone and burnished wood. A floating staircase bisects the area. Most tastings take place on a gracious patio beneath gently sinuous fabric canopies. In short, Jack and Miles wouldn’t recognize the place.
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After Sideways was nominated for five Academy Awards and won one, waves of travelers swept across Santa Ynez Valley wine country, located about two hours north of Los Angeles, many determined to follow in Miles and Jack’s footsteps. Twenty years later, they still do, and not long ago, my wife Pam and I joined them. Our mission: to find out what’s changed and what’s stayed the same along America’s most famous cinematic wine tour.
The Sideways Inn, Then and Now
One place that neatly straddles the gap between same and different over the last 20 years is the Sideways Inn in Buellton, where Miles and Jack stayed during their road trip. It’s a shrewd rebranding of the gloriously dumpy Windmill Inn depicted in the film–a two-story, three-star roadside motel that’s tucked between a Shell station, an RV park, and a Highway 101 on-ramp. A faux windmill still looms over the lobby entrance. The place has been renewed from the studs up. The modest rooms now feature walk-in showers, updated furniture, and comfortable beds. Our room even had a wet bar.
If you want to come close to the true Sideways experience, book room 234, where the interior scenes were filmed. In the parking lot just below that room’s balcony, Jack (Thomas Haden Church) is walloped with a motorcycle helmet by his temporary paramour, Stephanie (played by actress Sandra Oh). It’s payback for not telling her that he’s on his bachelor trip and due to get married in a few days.
The Hitching Post
As Pam and I discovered, you can still walk from the motel along Route 246, as Jack and Miles did both sober and sideways, getting buzzed by traffic and passing the iconic Chevy and Ford dealerships whose signs illuminate the way in the film. Within about half a mile, you reach The Hitching Post 2, the restaurant where movie viewers first lay eyes on the luminous Maya, played by actress Virginia Madsen.
“I was working the grill, and they wanted the flames to come up behind Maya when she first says hello to Miles,” recalled Frank Ostini, Jr., owner of the restaurant both then and now. “They must have done 11 takes. I had to keep running my hands underwater; they were getting so burned.”
Like the proprietors of many businesses we spoke with on our visit, Ostini said they were overwhelmed by Sideways pilgrims after the movie’s Oscar buzz pulled the quiet Santa Ynez Valley into the spotlight.
“We were packed every night for a few years running,” said Ostini, 72, who, in addition to running the restaurant, makes estimable wines. He was standing in his new tasting room in front of a wall of photos and mementos from the filming. The photos depicted Madsen and Oh gleefully punching down wine in big plastic vats and the cast and crew, including director Alexander Payne, posing for a group shot around a dinner table.
Co-Starring Pinot Noir
Ah, Pinot. The movie is a paean to that lovely, finicky grape. Due to a geological anomaly, a set of mountain ridges runs east and west between the Pacific and the Santa Ynez Valley, ushering in cool ocean breezes and creating perfect corridors to grow Pinot Noir and its sister cool-weather grape, Chardonnay. Average temperatures rise one degree per mile as you move inland, limiting the growing range for the varietals.
Miles waxes poetic about Pinots throughout Sideways, including one scene where he describes it as a “thin-skinned, temperamental” grape that “needs time and attention” to thrive–characteristics that, sadly, apply to him as well.
“We barely had enough Pinot to meet demand,” said Ostini. “We sold almost everything we had.”
The restaurant, specializing in regionally renowned barbecued steaks and other rustic fare, carefully sourced and prepared, has remained busy over the two intervening decades. Unlike some Santa Barbara County business operators, Ostini didn’t let his Sideways bounce go flat. His restaurant is still busy nearly every night, and his new tasting room is a testament to his operations’ continuing popularity.
“You’re only as good as the last meal you served,” added Ostini, 20 years after a moment of celluloid fame rocketed him to prominence.
What Miles and Jack Missed
Since Sideways has come and gone, some land in the Santa Ynez Valley has changed hands, and new money has moved in. This has altered the vibe, sometimes for the better.
For instance, the first place Miles and Jack visit in the film, Sanford Winery, is now Peake Ranch Winery. The new owner, hedge fund operator John Wagner, has restored the name of the property to honor its original owner, Channing Peake, a rancher and accomplished abstract artist who was a friend of Pablo Picasso.
The property now features a contemporary tasting room worthy of Napa Valley, an immaculate, high-science production facility, and 50 acres of pinot and chardonnay on slices of geography, offering varied exposures, each allowing different expressions of their grapes. Tastings take place on a terrace and deck overlooking gorgeous hills rolling with vines. The aromas that rise from the rosé are nearly ethereal.
But Sideways followers can still get their taste of nostalgia.
To get to Peake Ranch, they follow one of the country roads that unfurls in the background as the two buddies drive along. Upon arriving, fans can snap a selfie in front of a deserted ramshackle shed. It’s the place where Miles gives Jack an insufferable first lesson on how to taste wine. It ends with an exasperated Miles asking, “Are you chewing gum?”
Just Don’t Say Merlot
Perhaps the most memorable moment in Sideways is when Jack and Miles have an urgent conversation outside a restaurant in the town of Los Olivos. Jack is trying to convince Miles to keep things light during a double date with Maya and Stephanie.
“Do not sabotage me,” urges Jack, directing Miles not to spill the beans that in two days, he’s due to take his wedding vows. “And if they want to drink Merlot, we’re drinking Merlot.” Miles reluctantly agrees to conceal Jack’s deceit but draws a red line at Merlot. “If anyone orders merlot, I am leaving. I am not drinking any fucking merlot!” Some say that this throwaway line tanked Merlot sales.
In any event, the memorable double date scene was filmed inside the Los Olivos Wine Merchant & Cafe. The restaurant serves creative California cuisine, much of it grown on owners Sam and Shondra Marmorstein’s organic farm, just a mile away. The alley outside remains a Sideways touchstone; my wife and I saw a couple taking selfies on the spot one afternoon.
The inside of the restaurant remains quite recognizable, though there are no tables along the long wall of wine bottles where the dinner scene was shot. Sam Marmorstein says director Payne wanted tables moved there so wine bottles would be in the background. In the sequence, Miles drunk-dials his ex-wife from a payphone located in a fake hallway that was constructed only for the shooting.
My wife and I completed our Sideways tour by having dinner at the very site where Miles so famously sneers away Merlot. As we perused the wine list, I couldn’t resist asking the sommelier: “So, do you have any Merlot?”
Wine director Jonathan Lynn smiled, and retreated to the wine wall. He brought over a bottle from Paradise Springs Winery in Santa Barbara County. In brash gold letters, the label read “F’ing Merlot.” Twenty years after the release of the movie that so indelibly disparaged an otherwise worthy grape, rest assured you can now visit Sideways country and get yourself a fine bottle of f’ing Merlot.