As my kid’s 21st birthday approached, I asked about his plans. Beer with buddies? A party at his place?

“What I really want,” he said, “is for you and dad to show me Bend’s best cocktail bars.”

Wait, what? My stepson wants to spend his milestone birthday with…parents?

“You always talk about these really cool cocktail spots and I’ve seen drinks you order and I want to know what it’s all about,” he explained. “Can you take me out to do the ultimate cocktail crawl?”

My child…I’ve trained for this my whole adult life. 

Here’s how we planned the kiddo’s 21st birthday quest for Bend’s best cocktails.

Blogger Tawna with the kiddo on a Wanderlust Tours cave adventure 10+ years ago.

First, some disclaimers…

The goal of this adventure was not to get hammered. It’s to expose a brand-new adult not just to Bend’s cool, creative cocktail scene, but also to educate him on responsible drinking.

We Ubered or walked everywhere. We brought refillable water bottles and made it a point to hydrate. We paced ourselves. We filled our bellies with food to counter the effects of alcohol. 

Most of all, we set out to teach the kid that there’s a real art to Bend’s best cocktails. We discussed flavor profiles, quality spirits, and the importance of savoring it all.

Also, um…how did this kid get to be 21? Pretty sure he was nine when we met yesterday.

The first stop on the ultimate 21st birthday cocktail crawl is Rapa Nui Tiki Bar in Bend’s beautiful Old Mill District.

Stop #1: Rapa Nui Tiki Lounge

We start with Rapa Nui for a few reasons. This cool tiki lounge in Bend’s Old Mill District opens earlier than most spots on Saturdays. They also set a fun, funky tone with their tropical decor, unique drinkware, and a vibe that recalls our family’s trips to Hawaii. The upstairs balcony is a bonus on sunny afternoons.

The kiddo’s first pick was the Zombie: A fruity concoction of lime, grapefruit, cinnamon, velvet falernum, and dark rum topped with 151 and grenadine. He loved it wholeheartedly before tasting my favorite drink. 

Duke’s Pearl combines passionfruit, honey, lime, silver, and Jamaican rum, and when my kid stopped swooning, I suggested a birthday rule wherein he could taste each drink at the table and claim the best one as his own. 

We studied the food menu closely, explaining the pitfalls of drinking on an empty stomach. Rapa Nui’s Asian-inspired offerings present some challenges for a kid allergic to both peanut and sesame, so we opted for some shared bao buns. The carnitas one comes with chipotle aioli, slaw, cotija, and cilantro, while the fried tofu bun has vegan tofu mayo, miso vin, greens, and pickled red onion.

The verdict: Of all our stops, this one proved to be the kid’s favorite. Parenting win!

When weather allows it, the alley outside San Simon lends a cool European street cafe vibe to your Bend cocktail experience.

Stop #2: San Simon

Bend’s San Simon in historic Tin Pan Alley was one of our top picks once we reached Downtown Bend. Funky art, creative cocktail offerings, and their promise of “sophisticated debauchery” has made this one of our favorite stops since they opened in 2019.

The interior feels hip and cool, but the outdoor tables leave you feeling like you’re sipping at a European street cafe. That’s the vibe we wanted, and we knew the kid would get a kick out of learning new ingredients.

“What’s yellow Chartreuse?” he asked as he studied the menu. “Or how about Peychaud’s aperitivo?” 

It was a good chance to show him how we often end up googling ingredients when something’s unfamiliar. Who knew parents don’t have all the answers?

Once we’d explained the smoky qualities of mezcal, he was all in on the Thomas Edison’s Penultimate Dying Breath. It’s a mix of mezcal, pineapple, fresh lemon, and green Chartreuse. My order of Gin & Juice & Juice & Treusse (Wild Roots cucumber and grapefruit gin, yellow Chartreuse, Chinola passionfruit liqueur, fresh orange, and fresh lime) went down easy and gave the kid a chance to compare gin-based beverages versus mezcal-based ones.

Since we’re all fans of charcuterie, we passed around San Simon’s menu of meats, cheeses, and nibbly bites to pick what might pair best with the drinks. On a busy Saturday night, the arrival of drinks and eats didn’t time out great, but instead of ordering another round of booze, we pointed out San Simon’s awesome mocktail menu.

“We’re pacing ourselves,” we informed the man-child as we ordered one Calm the F**k Down (lavender, chamomile, ginger, soda, CBD), one Hibiscus Spirits (hibiscus, lemon, soda), and one Virgin Mama (ginger, rosemary lime, cucumber, soda). 

Mocktails for the win!

The newly-minted 21-year-old admires the art at the entrance of Dogwood Cocktail Cabin.

Stop #3: Dogwood Cocktail Cabin

From the cool art on the walls to the comfy sofas and funky wood tables, the vibe at Dogwood makes it one of our favorite cocktail stops. We always knew our artistic offspring would love this aspect of it Dogwood, and we weren’t wrong. 

The artsy vibe is enhanced by Dogwood’s expansive menu grouping cocktails by spirit. From vodka to gin to whiskey to tequila, we took our time telling the kiddo about each of the options while enjoying an order of Dog Food (popcorn, duck fat, bacon, parmesan, sea salt).

We’re well aware this young man didn’t spend his college dorm months drinking soda, and we’ve also shared tastes of wine, beer, and mixed drinks at home. But this is our first time really digging into the details of what makes a good cocktail (and for the record, Dogwood makes a darn good cocktail). 

Wanting to grasp the difference between tequila and the mezcal he had at our last stop, he ordered the Dogwood Margarita made with reposado, citrus, salted plum, and a red wine float. I went with my old standby, the Beatnik (beet infused vodka, ginger, and lemon), while the kiddo’s father got the Absinthe Minded (rye, cbd infused absinthe, pomegranate, and lemon). One taste of that and the birthday boy was hooked. “I like my margarita, but can I invoke the birthday rule and have that one instead?” 

But of course, young lad.

Stop #4: Dinnertime

Full-disclosure: We’d planned to take a break here and hit either Drake or 900 Wall for a meal and a chance to let our livers rest. 

But we may have been a little too exuberant in demonstrating the importance of filling our bellies at the previous three stops. None of us felt much like a full meal at this point.

Though we scrapped our dinner plans on this particular night, I highly recommend both these stops for a terrific meal and an excellent cocktail selection.

Moving on…

Blogger Tawna and the fam at Stihl Whiskey Bar with one of the ever-present HydroFlash water bottles they carried for the cocktail crawl.

Stop #5: Stihl Whiskey Bar

We had three potential picks for this next stop, and decided to let our mood set the course.

Astro Lounge makes terrific drinks and has live music most Saturday nights, and Velvet has a hip, younger vibe we knew the kid would dig.

But with Oktoberfest packing the Downtown Bend streets, we opted to stroll to the outskirts of downtown and another favorite spot, Stihl Whiskey Bar. They’ve got a mellower setting and a “locals’ favorite” rep that brings us here on bustling nights when we want a place with great drinks where we can still hear each other talk.

Despite the name, they’ve got plenty of options with no whiskey at all. That’s what the grown boy chose, selecting a vodka concoction dubbed Call Me Knight Hawk (360 Vodka, elderflower liqueur, fresh pressed grapefruit). I went with the Aztec Banana Old Fashioned (rye whiskey in a traditional old fashioned with a dash of Aztec chocolate bitters and a splash of banana simple syrup) and was not disappointed.

For something to nibble, we ordered a small plate of shishito peppers lightly fried and served with lemon garlic dressing. We took our time here, discussing the difference between drinks you sip slowly and those meant for heartier swilling.

Stop #5: O’Kanes

Here’s where I confess I’m too old to stay out late.

Wait, no. I mean I wanted the gents to have some father/son bonding time, so I summoned myself an Uber and bid the boys farewell for the evening.

They continued on to O’Kanes, which holds sentimental value for our fam. It’s one of the first watering holes the hubby and I hit together more than 11 years ago, and it’s also where I met the kids’ mother for the first time when it became clear we’d be doing the co-parenting dance.

This tucked-away bar on the McMenamin’s campus is adorned with church doors, stained glass windows, and an 1896 Round Oak potbellied stove. It’s unbelievably cool, and the fire pits outside make it even more awesome.

The best part for the boys? Sharing cigars around the fire as they chatted up locals and visitors and slowly enjoyed a pint of beer. While I don’t normally recommend mixing distilled spirits and suds, this is probably the way to do it (how does it go? “Liquor to beer, never fear; beer to liquor, never sicker.” Something like that).

This was also a chance for my spousal unit to chat with his son about learning when you’ve hit your limit and keeping track of friends who don’t want to keep going. They texted to make sure I got home safely in my Uber, and took their time deciding whether to continue.

The gents finish off the night with a stop at The D in Downtown Bend.

Extra credit: The D

Every good 21st birthday celebration should end in a dive bar, and The D&D Bar and Grill is a favorite for Bend locals. Cheap food like tots and chicken strips give the tummy some nice padding, and old standbys like the basic gin & tonic or a classic Jack & Coke offer a taste of what he’s most able to afford on his new-adult budget.

The boys gobbled up their fried goodness and ended the night feeling full and happy, and yep…pretty tipsy. 

But thanks to the Uber driver who got them home safely, and a healthy respect for Bend’s boozy scene, it was a 21st birthday to (mostly) remember.