Looking for the best bars in Bend, Oregon? You’re in the right place.
The short version
Bend punches way above its weight for cocktails. These are the six bars I send people to, ranked, with my top pick downtown.
- San Simón — my #1, a hidden gem tucked into Tin Pan Alley with the best cocktails in town.
- The Dogwood Cocktail Cabin — old-school charm, menu organized by spirit; now reopened at the Pine Shed.
- Velvet — speakeasy disguised as a plant shop, easy to walk right past.
- The Stihl Whiskey Bar — rare whiskey from all over the world, great for a first date.
- Waypoint — full-service bar from the Bend Brewing team, thoughtful cocktail list.
- O’Kanes — McMenamins cigar-and-whiskey bar with outdoor fire pits.
Speaking of beer, we’ve you covered in that department as well. Read: 15 Bend Breweries You Won’t Soon Forget.
Best Bars Bend, Oregon
(Click here for the table of contents)
For those asking, here’s the hotel we usually stay at while visiting Bend.
#6. O’Kanes (McMenamins Old St. Francis)
The McMenamin brothers, Brian and Mike, are nothing short of legend in Oregon. Hailing from Portland, the brothers have been transforming historic buildings at risk of demolition for four decades.
The Old St. Francis School is no exception. Built in 1936, this Catholic schoolhouse has since been repurposed as a hotel, pub, brewery, movie theater, cigar bar and secret speakeasy.
O’Kanes (which used to be the school’s garage) was transformed into one of the best bars in Bend. Part cigar bar, part whiskey bar, you’ll find a great selection of bourbon-forward cocktails.
Scan the menu for creative concoctions or stick to traditional cocktails, if that’s more your speed. The adventure is up to you! Grab your libation and park yourself at one of the outdoor fire pits with some good friends.
Local’s Recommendation: If you’re exploring town for the first time, read 20+ Memorable Things to Do in Bend.
#5. Waypoint
Waypoint is a full service bar from the folks behind Bend Brewing. There’s a thoughtfully-hand-picked cocktail menu in addition to Bend Brewing beer and a great wine list, you won’t want for much at this local spot.
If you’re overwhelmed by the exciting menu at this popular Bend cocktail bar, I suggest going with the Mezcalero (mezcal, vanilla, eucalyptus, cocoa, orange) for a unique twist on a classic. However, it’s hard to go wrong with anything on the menu.
#4. The Stihl Whiskey Bar
Contrary to popular belief, the Stihl Whiskey Bar doesn’t serve whiskey exclusively. The menu plays host to creative vodka, tequila and gin libations as well, so don’t be deterred by the name if you’re not a whiskey fan.
My husband, Will, is whiskey enthusiast (we toured 50+ whisky distilleries in Scotland last year). So, we went for the whiskey and were completely blown away by the variety on offer. They have whiskies from all over the world, including very rare (and hard to find) bottles.
But, as you can except, you’ll be paying top dollar for the rare stuff. Thankfully, the cocktails are fairly priced.
This Bend whisky 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 whiskey enthusiast to realize this is one of the best bars in Bend.
My pick — best for a first date
The Stihl Whiskey Bar.
Welcoming but sophisticated, with whiskies from all over the world (including rare, hard-to-find bottles) and cocktails that stay fairly priced. It’s the spot I’d pick to impress someone without trying too hard.
#3. Velvet Lounge
The Velvet Lounge gives off endearing speakeasy vibes. Disguised as a plant shop from outside, it’s easy to miss this popular Bend cocktail bar if you don’t know to look for it.
Once inside, head upstairs and place your order at the bar. You’ll be greeted with a fun menu featuring creative cocktails you won’t find elsewhere. The vibe is casual and relaxed and there’s always an old-school movie playing on the TV upstairs. It’s a fun time all around.
#2. The Dogwood Cocktail Cabin
Update: The Dogwood has reopened. After nine years downtown, it now lives in a renovated historic mill building (the Pine Shed) at 821 NE 2nd St in Bend’s Makers District, sometimes listed as “Dogwood at the Pine Shed.”
The Dogwood Cocktail Cabin is one of the oldest bars in Bend. From the funky mural adorning the wall, to eclectic art and aged leather sofas, it’s an irresistible old-school bar few can resist falling in love with.
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.
#1. San Simón
San Simón came highly recommended by a chatty local I ran into at 10 Barrel Brewing. I asked him about the best bars in Bend, and without batting an eye, he confidently recommended “San Simon.”
Intrigued, I asked for details. He told me it was a relaxed bar offering a great selection of exciting cocktails and whiskey. That’s all I 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 feels like a treasure hunt. Just follow the inevitable sounds of laughter and you’ll be there in no time.
The hardest part about the experience 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 opted for bourbon and I went with the wine. Between the cocktails and great spirits, this gem earned the number one spot on our list of the best bars in Bend. I bet you’ll love it too!
San Simón Happy Hour: Daily from 2-6 p.m. Select cocktails and house wine goes for $8.
My pick — best cocktail bar in Bend
San Simón, no question.
Tucked into Tin Pan Alley downtown, finding it feels like a treasure hunt. We settled in for two hours, and after visiting firsthand I can say these are some of the best cocktails in Bend. It earned the #1 spot on our list. The daily 2–6 p.m. happy hour ($8 select cocktails and house wine) is the move.
List of the best cocktail bars in Bend (Post Overview)
In sum, here’s a list of the best bars in Bend, Oregon. Cheers!
- San Simón
- The Dogwood Cocktail Cabin
- Velvet Lounge
- The Stihl Whiskey Bar
- Waypoint
- O’Kanes at McMenamins Old St. Francis School
Map of Bend’s best bars
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Cheers,
Antonina
