Looking for the best bars in Bend, Oregon? You’re in the right place!

I spent all of last summer living in Bend and learned a thing or two about the city’s best bars and the best cocktails in Bend. So if you’re set on celebrating a special occasion, or simply catching up with friends and need to take a break from the beer, this list of the best Bend bars may prove helpful.

Speaking of beer, we have you covered in that department as well. Read: 15 Bend Breweries You Won’t Soon Forget.

Best Bars Bend, Oregon

#6. O’Kanes (McMenamins Old St. Francis)

Oh man, this place is so cool. My husband and I are avid fans of the McMenamin brothers.

The McMenamin brothers — Brian and Mike — are nothing short of legend around the state. Hailing from Portland, the two brothers have been transforming historic buildings at risk of demolition for four decades (and counting).

They strive to preserve the charm of these historic places and go so far as to hire historians to ensure important details aren’t overlooked.

The Old St. Francis School was a Catholic schoolhouse built in 1936 that has since been transformed to a hotel (the classrooms were turned into hotel rooms), pub, brewery, moving theater, cigar bar and secret speakeasy.

O’Kanes (used to be a garage) was transformed into (what would later become) one of the best bars in Bend. Part cigar bar, part whisky/bourbon bar, you’ll find all the usual suspects when it comes to boozy bourbon-forward cocktails.

Peruse the menu or order your usual before parking yourself near an outdoor fire-pit or (if visiting in the winter) the age-old stove inside (I swear this thing is so old it probably voted for Eisenhower.

Further Reading: 20+ Epic Things to Do in Bend, Oregon

#5. Waypoint

Waypoint is a full service bar that’s the passion-project of the folks behind Bend Brewing. Featuring a thoughtfully curated cocktail menu, 8 taps of Bend Brewing beer and a great wine list, you won’t want for much at this popular Bend cocktail bar.

If you’re overwhelmed by the exciting cocktail menu, I suggest going with the Mezcalero (mezcal, vanilla, eucalyptus, cocoa, orange) for something unique or a classic margarita with mezcal for a fun twist on an original.

#4. The Stihl Whiskey Bar

Contrary to popular belief, the Stihl Whisky Bary doesn’t serve whisky/bourbon cocktails exclusively. The menu plays host to creative vodka, tequila and gin libations as well (among others!) so don’t be deterred by the name if you’re not a whisky fan.

My husband, Will, is whisky enthusiast (we toured 50+ whisky distilleries in Scotland). So, we went for the whisky. We were completely blown away by the selection on offer. They have whiskies from all over the world, including very rare (and hard to find) varieties.

But, as you can except, you’ll be paying top dollar for the rare stuff. Thankfully, the cocktails are fairly priced.

This Bend bar has a welcoming yet sophisticated vibe, making it a great spot to take a first date you’re keen to impress. You don’t need to be a whisky enthusiast to realize this is one of the best bars in Bend.

#3. Velvet Lounge

More-so than any other place mentioned on this list of the best bars in Bend, the Velvet Lounge exudes endearing speakeasy vibes. Dressed like a plant shop from outside, it’s easy to miss this beloved Bend cocktail bar if you don’t know to look for it.

Once inside, you’ll see a downstairs and upstairs area overflowing with plants. Head upstairs and place your order at the bar. You’ll be greeted with a fun menu featuring creating cocktails you won’t find elsewhere.

The vibe is casual and relaxed and there’s always an old-school movie playing on the sole TV upstairs. This is a great Bend bar for pre-dinner drinks, setting a fun tone for the rest of the evening.

#2. The Dogwood Cocktail Cabin

Note: After 9 years downtown, the Dogwood Cocktail Cabin is moving locations! I’ll update this post once they settle on the new locale. Stay tuned.

The Dogwood Cocktail Cabin is one of the oldest bars in Bend. From the funky murals that adorn the wall, to elective art and aged leather sofas, this Bend bar has an old-school vibe that makes it irresistible.

The menu is organized by spirit, making it easy to pick a libation of your preference. I’ve ordered from all sections of the menu and tend to lean towards the gin and tequila/mezcal drinks.

Regardless of what you order, buckle in, you won’t have reason to leave anytime soon.

#1. San Simón

San Simón came highly recommended by a local I met while sipping brews at 10 Barrel Brewing. I asked him about the best bars in Bend, and without batting an eye, he came back with a confident “San Simon.”

Intrigued, I asked for details. He told me it was a relaxed bar vibe offering a great selection of creative mixed cocktails and whisky. That’s all we needed to hear, we grabbed our checks and made a beeline for downtown.

Tucked into Tin Pan Alley, San Simon is located in the heart of downtown, but it’s slightly out of sight. Finding it for the first time feels a bit like a treasure hunt. Just following the sounds of loud laughter and you’ll be there in no time.

The hardest decision of the day is choosing between outdoor and indoor seating. The outdoor area has a very casual vibe while the indoor area is more eclectic. Since we were visiting on a hot day, we opted for indoor seating and settled in for two hours.

After visiting firsthand, I can confirm that these are some of the best cocktails in Bend and shouldn’t be missed. For round two, my husband and friend opted for bourbon (they said the prices were fair and couldn’t pass them up) and I went with the wine.

San Simón Happy Hour: Daily from 2-6 p.m. Select cocktails (the Old Fashioned, Sazerac, well and houseman tonic and) house wine goes for $8.