Sightseeing Sideways: Reliving the movie makes for a great weekend

BUELLTON, Calif. – The rolling hills of the Santa Ynez Valley are the perfect backdrop for some college friends to reunite and enjoy some fine dining and the region’s wine.

Nestled in these hills are dozens of wineries, each has its own distinctive and charming feel. Located about an hour north of Los Angeles, the Santa Ynez Valley wine region is often overlooked with Napa Valley and Sonoma garnering most of the attention. But the wine produced in the valley is nothing short of spectacular.

With the box office success of “Sideways” in 2004, the region’s prominence has increased, attracting thousands of visitors to the area who want to experience the movie. “Sideways” tells the story of college roommates Miles and Jack during the week leading up to Jack’s wedding.

In addition to putting the Santa Ynez Valley on the map in many people’s minds, the movie is said to have helped grow sales of pinot noir while leading to a decrease in merlot consumption. Of pinot, Miles said, “its flavors, they’re just the most haunting and brilliant and thrilling and subtle and … ancient on the planet.”

Sightseeing “Sideways” and visiting the many places that served as the setting for Miles and Jack makes for a simple and enjoyable getaway. The movie was filmed at a number of local establishments and wineries, including Firestone Winery, Sanford Winery and Fess Parker Winery (known as Frass canyon in the movie). Traversing the winding roads that connect the dozens of wineries offers beautiful vistas.

Just off Highway 101 sits a Days Inn motel, a relatively non-descript building with the exception of a large windmill over the hotel’s lobby and the fact that this motel played a starring role in the movie adaptation of Sideways.

An affordable lodging option, the motel – referred to as The Windmill Inn in the movie – is the perfect starting off point for anyone looking to relive the Sideways experience on a Sideways tour of the Santa Ynez Valley. As Rex Pickett, the author of the book wrote, “not exactly the Four Seasons, but serviceable.”

The Hitching Post II on E. Highway 246 in Buellton is featured in the movie. While it’s a must-see to complete the Sideways experience, it’s also can’t miss destination because of its food and wine.

The restaurant boasts having the “Best BBQ steaks” and one taste of their filet mignon seasoned with the restaurant’s signature Magic Dust makes a compelling argument. While at the restaurant, complete the experience by ordering a bottle of the restaurant’s Highliner pinot noir wine – the same wine that Miles and his friends drink in the movie.

One last restaurant that is a must for fans of the movie is the Los Olivos Café & Wine Merchant, located in nearby Los Olivos. The restaurant is known for its distinctive California-Mediterranean cuisine and features an extensive wine collection. The restaurant offers Sideways menu selections featuring actual dishes served in the movie.

Of course, outside the restaurant is the alley where Miles exclaimed that he would not drink any Merlot at dinner – “I am not drinking any (expletive) merlot,” to be exact. A reenactment of the exchange is a must. And judging by the reaction my friend and I received as we exchanged lines – “say the lines,” a passerby shouted – it’s not an uncommon occurrence.

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About Todd DeFeo 1647 Articles
Todd DeFeo loves to travel anywhere, anytime, taking pictures and notes. An award-winning reporter, Todd revels in the experience and the fact that every place has a story to tell. He is the owner of The DeFeo Groupe and also edits Express Telegraph and Railfanning.org.