When the snow begins to blanket Central Oregon, there’s no better way to embrace the chill than with a cocktail designed for the season. Whether you’re cozying up indoors or gathered around an outdoor firepit, these winter drinks blend local flavors, bold spirits and a touch of creativity to keep you warm. From spiked hot chocolates to inventive takes on the classic hot toddy, here are the best places to sip your way through the season.
Bar Rio – Naughty & Nice Holiday Cocktails Series
“We’re having some fun with the holiday spirit,” says Amy Draheim of Bar Rio’s holiday menu. The team is rolling out a “Naughty & Nice” cocktail series all December long. On the Nice List, expect comforting flavors and local ingredients, like Thump Coffee, Holm Made Toffee and Glacier Gourmet, perfect for pairing with some falling snow.
The Naughty List, on the other hand, pushes the holiday boundaries with creative mocktails and richer cocktails. Imagine hot cocoa topped with an entire dessert garnish or a bold espresso Negroni designed to power you through the season’s long nights. Pop in all Demember long to see what the team at Bar Rio is mixing up behind the bar.
McMenamins Old St. Francis School – Hot Chocolate Orange
“This drink combines the best of winter’s classic flavors—rich chocolate, bright citrus and a warming spirit,”* says McMenamins’ Justine Goodiel. The Hot Chocolate Orange takes the traditional hot cocoa and gives it a luxurious twist with Cheshire orange liqueur, your choice of High Council Brandy or Hogshead Whiskey and a dollop of whipped cream. “The inspiration came from those oranges we used to find in our Christmas stockings,” Goodiele shares.
The result? A drink that feels nostalgic and indulgent in all the right ways. Whether you’re sharing stories around McMenamins’ fireplaces or relaxing after a holiday shopping spree, this is the kind of drink that makes winter feel magical.
San Simón – Hot Toddy
“Since we opened five years ago, I’ve been proud to say we have the best hot toddy I’ve ever had anywhere,”* says Brian Trottier, the owner of San Simón. It’s not just talk—this hot toddy has a cult following, thanks to its fresh, thoughtful ingredients. The base is a ginger-rosemary simple syrup, made in-house by juicing fresh ginger and steeping rosemary in hot water.
Add freshly squeezed lemon juice, hot water and your choice of spirit (rum is the house favorite), and you’ve got a drink that’s both invigorating and soothing. “For mezcal lovers, we add a dash of hibiscus simple syrup, which gives it this subtle floral note that’s really special,”* Trottier explains. And yes, the toddy is reason enough to visit, but the real magic is sipping it outside in one of San Simón’s heated cabins, watching snowflakes fall around you.
Jackalope Grill – Bourbon Fireside
At Jackalope Grill, the Bourbon Fireside cocktail is as comforting as its name suggests. Made with fresh hot apple cider, Basil Hayden Bourbon, a spritz of orange zest and a cinnamon stick, it invites you to slow down and savor the season. “There’s something magical about wrapping your hands around a warm glass and letting the steam rise on a chilly day,” says Laura Bliss of Jackalope Grill.
The bourbon adds depth and warmth, while the orange zest and cinnamon stick give it just enough brightness to feel festive. It’s the kind of drink that doesn’t need any bells and whistles—it’s simple, perfectly executed and best enjoyed with friends after a day in the snow.
Currents at the Riverhouse Lodge – Avalanche
Currents at the Riverhouse Lodge in Bend, Oregon, is offering a signature cocktail called the Avalanche, which combines the boldness of an espresso martini with the creaminess of a White Russian, and adds a local twist with Crater Lake Hazelnut Espresso Vodka. The cocktail is ideal for festive gatherings or a quiet evening by the fire, and can be paired with chair massages to melt away any slope-induced tension. The Avalanche is available starting in January. Read our full feature on this cocktail, here.
Hungry for More? Check out more of what Central Oregon’s dining scene has to offer all year long with our dining guide.
Next up, read: Cozy Cafes and Bars in Central Oregon: Where to Warm Up This Winter
