Overview:
The Old Fashioned cocktail is classy without trying too hard- perfect for a laid-back town like Bend.
Ordering a martini — shaken, not stirred — can make anyone feel like James Bond. But in a laid-back town like Bend, that classic line might come off a bit too polished. For a drink that nods to timeless style without trying too hard, consider an Old Fashioned. It’s vintage, it’s classy and it fits right in.
Although the Old Fashioned cocktail is rarely seen in Bond’s film appearances, it appears far more often in Ian Fleming’s original novels, where the literary Bond often prefers it alongside his Scotch and soda.
The Old Fashioned traces its roots to the early 1800s, when the term “cocktail” was defined as a mix of spirit, sugar, water and bitters. By the 1860s, this formula was so well known that bartenders began calling it an “old-fashioned” to set it apart from newer, more elaborate drinks.
During Prohibition, bartenders added oranges, cherries and other fruits to mask the harsh flavors of low-quality spirits. But after Prohibition ended and spirit quality improved, the original, stripped-down Old Fashioned recipe made a comeback.
The Old Fashioned’s continued popularity is a testament to its simple formula and lasting appeal. It’s a classic that never tries too hard, making it perfect for channeling your inner Bond at your next local Happy Hour.
Whiskey Wednesdays at McMenamins Old St. Francis School
Feeling rebellious? Order your Old Fashioned in a Catholic schoolhouse—well, a former one. This unique 1936 Catholic schoolhouse has been transformed into the distinctive Old St. Francis School hotel in downtown Bend.
Here, guests can explore secret hallways and hidden bars, soak in a mosaic-lined pool or catch live music and movies onsite. Enjoy an Old Fashioned at the Fireside Bar, where you can sip the classic cocktail made with Kentucky Straight Bourbon, Angostura bitters and sugar for just $8.25 on Whiskey Wednesdays. The bar also offers all-day Happy Hour pricing on Service Industry Mondays for those with valid food handler or liquor permits, and Take Care Tuesdays for health care workers with ID.
Happy Hour
Sun-Thu, 3-6pm
700 NW Bond St., Bend
Sophistication at San Simón
For those seeking Bond-level sophistication, San Simón is your destination. Tucked away in Tin Pan Alley, San Simón exudes an air of mystery. Outside, cozy firepit tables invite you to relax; inside, soft lighting, vintage decor and intimate seating create a romantic ambiance.
San Simón’s website captures it perfectly: “delicious drinks, simple food, exceptional service in a bohemian candle-lit room, down a dark romantic alley, overseen by a paper maché replica of a Mayan demigod with a penchant for bad behavior.”
Happy Hour
Daily, 3-6pm
845 Tin Pan Alley, Bend
This article appears in Happy Hour Guide 2025 and the Source September 18, 2025.
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