By Mo Sherifdeen

The ad was intriguing. The premise was simple: one night, eight bars, one bus. No, this was hardly your typical Friday night frat party. Instead, “Cocktails for a Cause” was Portland’s only bar crawl benefit event.

When I figured out that the event was a benefit for Live Wire! (read about them here) and took participants through some of the best watering holes in Portland (as featured in the February 2007 issue of Portland Monthly), I was sooo there!

While Oregon’s craft brewers and wine makers have garnered an international reputation for their libations, savvy mixologists and intrepid craft distillers such as SakéOne, Bendistillery (Crater Lake vodka), House Spirits Distillery (Medoyeff vodka, Aviation gin) and New Deal Distilled Spirits (New Deal vodka) have quietly transformed Oregon into one of the hidden gems of the cocktail world. Borrowing a page from local chefs, mixologists are creating seductive cocktails infused with local ingredients and fresh fruit such as berries, watermelons, pumpkins and yes—even avocados—while perfecting classics such as sazeracs and negronis. And so with the intoxicating spirit of liquid adventure in mind, my wife and I eagerly signed up to be part of the bar crawl.

4.00 pm: The Crawl Begins. After checking in for the weekend at the elegant Hotel Monaco, a luxurious boutique hotel near Pioneer Square, we headed to meet our fellow crawl cohorts at the first stop on the tour, El Gaucho on Broadway. This upscale dining establishment features dark wood furnishings and is a throwback to the classic steakhouses of a bygone era. Renowned for exceptional entrees, unparalleled tableside service, and a wicked drink menu, we were greeted here by our hosts for the evening, Nicole Vogel, the highly effervescent publisher of Portland Monthly, Connie Apa, the the magazine’s event organizer, our friends at Live Wire! Robyn (producer) and Pat Janoski (siren of sound) and our crawl emcee, the outrageous Miss. Poison Waters, Portland’s favorite man-in-dress.

No bar crawl can get underway without drinks and true to tradition, the friendly mixologists started to pour their salacious mixers. I was immediately drawn to the luxurious P-town Side Car, a delicious cocktail featuring cranberry infused Tuaca with blood Orange juice and topped with champagne while my wife went wild over what she swears is the best drink she’s ever had – the Ruby. The Ruby is named in honor of chief mixologist Mark Joseph’s daughter and is essentially a lemon drop with a hint of grenadine served on a sugar rimmed glass (in case you’re wondering, there’s another drink on the menu named for his son).

The night was just starting and we were already perfectly happy to hang out ‘til closing time and taste sipping Mark’s other creations…but the bus arrived and the crawl was on!

5:15 pm: Shaken n’ stirred….Next up was the Marble Bar at the Heathman Hotel. The Heathman is a famed Portland landmark and was recently named one of the “World’s Best Places to Stay” by Condé Nast Traveler and one of the “500 Best Hotels in the World” by Travel + Leisure magazine. Local imbibers also hit the Heathman’s all-marble bar for old-world ambiance and a chance to sample the earliest cocktails ever created such as the Old Fashioned Whiskey cocktail and the Manhattan 1874 that’s stirred exactly 30 times. The bar-hoppers were greeted here with classic gin martinis – Oregon’s Aviation gin, vermouth, and of course the stuffed olive. Bottoms up!

5.55 pm: The Wall. After a brief sojourn at the Heathman, it was on to my favorite stop of the night. Paddy’s Bar & Grill is located in an old historic building, just one block from the Waterfront Park on Yamhill and is the kind of place where you would expect everyone to know your name. This high-ceilinged bar is cozy, unpretentious and a perfect spot to chill out with a group of old friends, reminiscing about life, college or work. Paddy’s claims to have the biggest and most well stocked liquor shelves in the state, boasting a multi-tiered, 20-foot shelf behind the bar containing more than 400 bottles of liquor.

As we stared at the wall with a mesmerized glaze over our eyes—thinking about the endless possibilities that lay before us—the mixologists made life easier by serving up the Pama Peacock, a zesty concoction of Ketel One, triple sec and pomegranate liqueur and the Fedora, a brawny drink that packed punch so powerful that I don’t recall what was in it (seriously).

Paddy’s was also the location of our first local “celebrity” sighting. Marc Acito, author of the critically acclaimed coming of age novel, How I Paid for College: A Novel of Sex, Theft, Friendship & Musical Theater, joined us to promote his new book and talk about why he loves Portland so much (he moved here from the east coast) over a round of Peacocks followed by delicious crab cakes and jalapeno poppers.

6.45 pm: Gin in the Pearl. After a short jaunt along the waterfront on Front Avenue, our next stop was the cleverly named Olive or Twist. Located adjacent to Jamison Square in the trendy Pearl District, this watering hole pays homage to the all-mighty martini. Much like the classic martini, everything about this Dickens inspired bar is understated and sleek. The minimalist interior décor consists of sparsely decorated grey walls, intimate lighting, and a frosted glass wall that provides patrons privacy from passersby. Top selections here are the aptly named Rose City Martini, a fragrant bouquet of cucumber-infused gin, rose water and lime and the sugar-rimmed Peruvian, a blend of pepper vodka, mango and lime and garnished with chilies. The crawlers were served Stoli Elite martini’s and glazed chicken skewers.

7.35 pm: Southern Comfort. By the time we boarded the bus for the eight minute ride across the 405 bridge, we were all feeling warm and friendly and the conversation was loud and free flowing. The congenial mood spurred impromptu standup routines by Miss. Poison Waters and Nicole – an impressive feat given the number of stops on the tour so far. But I digress…

Our next stop was Roux, a Louisiana inspired bistro offering great favorites such as shrimp Creole and grilled oysters. This was my first time at Roux and I was really impressed with the comfortable vibes of the dining room and the intimate arrangement of the bar area. We experienced true southern hospitality here with a pair of Creole cocktails, the bold and bracing Sazerac (one of the oldest known cocktails), made with cognac, bitters and absinte, along with the more genteel Acadiana made with vodka, lemon juice and lavender. Laissez Les Bons Temps Rouler!

8.20 pm: 820 Lounge. The night was fleeting by and we were already at our sixth stop! We were now further up the North East side of Portland at made our stop at 820. Owner Lucy Brennan was recently named among Food + Wine magazine’s top five mixologists and the drink menu filled with more than 40 unique cocktails—such the zesty avocado daiquiri and dragon milk, SakeOne, muddled coconut, lemon-lime juice and half & half—is a testament to her ingenuity and creativity.

The music was pumping and the cool cats were soaking up Brennan’s elixirs as we undulated our way through the 18-foot bar that winds through this lofty old warehouse building to the dimly-lit plush “sunken living room” in the back. We were soon swooned with two of 820’s signature drinks, the Ruby (my favorite here), a beet infused vodka with just a splash of lemon-lime juice and the 816, citrus vodka with lemon-lime juice and passion fruit puree.

We spotted our second local “celebrity” here. April Baer, host of OPB’s Morning Edition along with her fiancé (a sports reporter at the Oregonian) joined us to chat about life, basketball (The Oregon Ducks were in the Sweet Sixteen!) and Live Wire!

9:10 pm: Gilt Club. We headed over the Broadway Bridge back to the west side of town. The penultimate stop on this rolling party was the elegantly chic Gilt Club. With posh red booths, relaxing brown curtains, dimly-lit “urchin” like lighting, and the sultry sounds of the ‘60’s in the background, the Gilt Club is a great place for both a first date or romantic evening with a longtime lover. While the menu looked exotic (spaghetti with North African spiced lamb sausage for example), the club is famous for its classic drinks such as the Moscow Mule, a legendary drink that kicked off the thirst for vodka in the U.S. back in the 1950s. The “mule” is traditionally served in a copper cup and is made with vodka, ginger beer, and lime. Also not to miss on the menu is the Idillic – a quixotic combination of serrano peppers, tangerine vodka and muddled dill…potent yet delicious!

9:50 pm: Saucebox. Six hours, seven bars and many drinks later, the party caravan finally ground to a screeching halt a few blocks from our starting point at the uber cool Saucebox, arguably one of the places that launched Portland’s cocktail craze (Lucy Brenan worked here). This swanky party spot has a knack for dishing some of the best Pan-Asian and Pacific Island cuisine in the city along with a dizzying array cutting-edge drink choices. And with 68 varieties of vodka, 33 tequilas, 26 rums and 20 bourbons, you’ll never be at a loss for what to order. The minimalist interior of this high-ceilinged spot consists of black-grey walls, large mirrors and votive candles conducive for secret glances and people watching. On top of that, DJ spun techno/house grooves adds a distinctive cosmopolitan flare to your experience.

The exhausted but upbeat partiers were provided the most popular drink in the house….the “Best Drink” – gin muddled with mint, ice and lemon-lime, topped with ginger brew along with a second round of ginger cosmos and an exotic array of delicious sushi and satay.

Tired but still buzzing with the excitement of having sampled the cream of Portland’s growing list of swankiest party spots, we headed back for good nights rest at the Monaco. So whether you’re hankering for a classic martini, a sazerac, an exotic avocado daiquiri, or just some foo-foo drink, there’s a watering hole with your name in it in Oregon!

~ Cheers!

about author Mo Sherifdeen

Mo is Travel Oregon's content publisher and loves to hike the forests and mountain trails of Oregon with his wife, daughter and dog. He is also known for getting lost inside a maze of books at Powell’s, sipping an IPA (or two) and seeking the best fish 'n chips along the Oregon Coast.

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