Go wine + spirit tasting with Bend’s Drinkable Diversions

Let’s be honest, beer in Bend is amazing, world-class even, but there’s more to drinking in Bend than just beer. So, if you’re not into beer or just curious about the world beyond, we’ve carved out a path next to the Bend Ale Trail just for you. We call it Drinkable Diversions, an adventure for equal-opportunity consumers whose palates light up with any well-crafted beverage.

The trail begins at the Bend Visitor Center to obtain a physical passport. Next, begin the self-guided and self-paced journey to collect stamps at each location. We encourage you to collect flavor memories from each spot, too, but for all you treasure hunters, it is not required. Once you visit three or more locations, come back to the Visitor Center to claim up to two prizes. You must be 21 or older and you don’t have to buy anything to get your stamp. (We do encourage you to support our local makers in other ways, if you can.)

Here are the Drinkable Diversion’s stops. Have fun! And please don’t drink and drive. 

A trail for wine tasting rooms, cideries, and distilleries near Bend

Oregon Spirit Distillers

Oregon Spirit Distillers is that rare gem that combines an obsession with great spirits like whiskey, a family-run business, the use of local ingredients to create a sense of place, and a location right in the middle of everything. OSD sits in the middle of Bend, surrounded by great beer, great coffee, and not far from The Last Blockbuster. They often have tasting festivals where you can meet distillers from all over Oregon, too.

Bend Cider Co

For those of you who may not know, Tumalo is the blip on the map between Sisters and Bend with several reasons to stop, all of which sit within the distance of a respectable disc throw. Bend Cider Co. is one of them. Keep it simple with the Dry Apple Cider, go tropical with the Guava Hibiscus, or celebrate the diversity of flavors with the Blackberry Ancho. 

Tumalo Cider Co.

Tumalo Cider Co., now a part of the Oregon Beverage Collective, built its reputation on making craft, nuanced, artisanal, small-batch cider. Bend Cider and Tumalo Cider sit around the corner from each other. Across the street you’ll find a cool outdoor food truck lot called The Bite Tumalo. That’s three great places to visit in fewer steps than pacing the sideline of your kids’ soccer game. 

Broken Top Mountain Whiskey

When you stop in Sisters, I hope you love gorgeous views, beer, coffee, art, quilts, folk music, and some tasty marionberry scones. But, let’s add one more: American Whiskey. Stop at Broken Top Mountain Whiskey to taste Oregon in a glass with whiskeys aged in American oak barrels and cut to proof with crisp Cascade water. Think bourbons, ryes, and Central Oregon skies.  

Bendistillery

While Bendistillery also has some amazing gin and infused vodkas, it’s their whiskey that keeps me coming back. I urge you to try the Black Butte Whiskey, a collaboration with Deschutes Brewery. But if you love an Old Fashioned, the Rock and Rye is a staple. Confused over the name? In April, 2026, Hood River Distillers, one of the largest and oldest importer, distiller, producer, and marketer of distilled spirits in the Pacific Northwest, announced that it was taking over the Crater Lake Spirits line from Bendistillery. 

Faith, Hope & Charity Vineyards

Faith, Hope & Charity Vineyards may seem like a ways out of town between Sisters and Redmond, but the 30-mile drive is worth it. When you finally step out of your car and see the view of its namesake (Old maps sometimes show the Three Sisters as Hope, Faith, and Charity), the only thing left to do is to pick your jaw and have delicious wine. Think of it as your private mountain enclave, but with a cellar full of spectacular wine. You might want to call ahead; this is a popular place to get married. 

Gompers Distillery

There’s a saying: that which grows together goes together. In Central Oregon, we love our juniper trees, juniper berries, and the true taste of the region, gin. Gompers Distillery in Redmond serves up its own gin and vodka cocktails in a speakeasy, filled with jazz, stories, and secrets. Feel free to show up in a flapper dress, which goes together like a drink and a smile. 

Lazy Z Ranch Wines

Lazy Z Ranch Wines is a working ranch close to Sisters that goes big on regenerative practices, where bees, animals, and people all play a role in keeping the land healthy. You can taste that in every glass. Lazy Z specializes in unforgettable meads made with honey from bees kept on the property and “ranch wines,” which are meads flavored with local fruits like blueberries and raspberries or even fireweed blossoms. You’ll also find ciders, beers, and kombucha, as well as charcuterie, food trucks, and of course, honey.