Rustic, but not rugged. Offbeat, but not off the beaten path. Self-aware, but also self-deprecating. The best coffee and craft beer, a mighty music scene, restaurants both trendy and traditional, and incredible natural scenery. Sound like somewhere you want to be? That’s Portland, Oregon, and chances are your friends want to be there, too.

For a pre-wedding celebration that will keep you entertained for days (and keep your friends talking for years), plan a Portland bachelor party and get to know one of America’s most fascinating cities.

For Getting Crafty (with Brews)

Let’s dive right into the reason you chose Portland for your bachelor party: it’s the breweries, right? Bar hopping in Portland is fun and easy, since there are so many hometown pubs serving small-batch craft beers. Whether you like a bright IPA made with flavorful Willamette Valley hops or a deep dark stout, your Portland, Oregon bachelor party runs no risk of running dry.

“But where can I bar hop in Portland?” you may be wondering. Glad you asked! One of the easiest, most entertaining ways to drink your way through this famed brewers’ town is by bicycle. On an Oregon Brewery Trail Bike Tour, you’ll taste a little of everything that makes Portland great at several beloved local breweries while cycling through the city.

For Wheels Along the Willamette

One of Portland’s nicknames is Bridgetown, and that comes from the 12 bridges that span the Willamette River to connect East and West Portland. (Fun fact: the Willamette is one of the few rivers in the Pacific Northwest that flows south to north.) The best way to experience Portland’s bridges and scenic waterfront is by bicycle. And luckily, Portland is a city with a deeply embedded cycling culture, where bike lanes and cycling trails abound. Rent a set of wheels at Cycle Portland and wheel your way around town to experience Portland like a local.

For Culture Kings

Portland is a big city for a small town. Though it’s easily navigable and fairly compact, Portland boasts some pretty impressive museums and exhibits. OMSI, the Oregon Museum of Science and Industry, is a deeply absorbing, interactive museum of both permanent and changing exhibits. There’s a planetarium, a big-screen theater showing a rotating selection of films, and—just outside the museum, in the river—the USS Blueback, a decommissioned Navy submarine from the 1950s. OMSI is a fantastic place to blow off steam with your favorite dudes and learn a few things along the way.

A more traditional, but equally enjoyable, museum in Stumptown is the Portland Art Museum. Highlights include the Native American Art collection, which features artwork both ancient and modern from Pacific Northwestern tribes. There are also global art collections and rotating exhibits, so there’s always something new to see.

For Part-Time Hipsters

Portland is known as a hipster haven, but you don’t have to be tragically hip and deeply ironic to enjoy the best of Portland’s offbeat culture. Powell’s City of Books is several stories high, takes up a whole block, and is one of the most legendary independent bookstores in the USA.

You can get lost easily in its labyrinthine bookstacks (not that we think that’s a bad thing!). Used and new books are sold side-by-side, making it simple to find a price that suits you. The rare book room is a treasure trove of first editions, out-of-print works, and historical leather-bound tomes. And of course there’s a café inside Powell’s—this is Portland, after all! Grab the guys and meander the awe-inspiring halls of Powell’s, and don’t be surprised if you emerge several hours later than anticipated.

Another important part of Portland culture is record collecting. If you’ve got a vinyl fetish, or just want to dig what the locals are into, walk a few blocks west of Powell’s and find Everyday Music. It’s a mecca for new and used music of all kinds, with vinyl in heavy rotation. You and the crew can browse your old favorites or check out some local artists.

For Cool Kids

One of Stumptown’s most beloved local venues is the Crystal Ballroom. You can hear live music of all sorts in this upstairs concert hall year-round. While many eclectic genres have rocked the stage of the Crystal Ballroom, the vibe skews toward indie rock and hometown heroes, with bands like the Shins, the Dandy Warhols, the Decemberists, and Sleater-Kinney among the roster of acts booked at the Ballroom.

For an epic night of partying like a true Portlander, check out the Crystal Ballroom’s calendar of events and find out who will be playing while you’re in town—there are usually shows several nights a week. And it’s one of the best last-minute bachelor party ideas you could wish for.

For Hungry Lads

Portland’s culinary scene is second only to its booze scene (okay, and its coffee scene, and its music scene…Portland has a lot of top-notch scenes). Restaurants range from gastropubs to global eateries to vegan cafés. Your Portland, OR bachelor party will never go hungry in a city as gastronomically diverse as P-town:

  • Nicholas Restaurant, a Mediterranean and Lebanese restaurant on Portland’s east side, serves bring-a-tear-to-your-eye good Middle Eastern food in a relaxed atmosphere that’s ideal for big groups. Freshly baked pita is served family-style, the food is colorful and flavorful, and there are even numerous gluten-free menu items for the food-allergic fellows in your group.
  • A true taste of Ireland in the Pacific Northwest, Kells Irish Pub is warm, boisterous, and perfectly suited for a gang of guys. The pub grub is great—try the Irish nachos—and there’s live music nightly. Of course, there’s also a great selection of draught beers, from the ubiquitous Guinness to a range of local brews.
  • If you’re looking for an excuse to slip into a suit and tie and have an ultra-classy stag night, look no further than RingSide Steakhouse. It’s a joint that doesn’t just look old-school…it’s actually been in business for 75 years. On the menu, you’ll find tender aged steaks, hundreds of wines, and a Sour Cream Vanilla Cheesecake that might change your life.

For Party Animals

Portland by day is beautiful, but Portland by night is unforgettable. You might assume that a city with such a well-established music and cabaret culture has some great nightclubs—and you’d be right.

  • Dante’s is a burlesque, cabaret, and rock bar where you can see live shows of all colorful kinds. You’ll find Sinferno Cabaret, the house burlesque troupe, performing every Sunday night. They were voted one of the top 10 burlesque shows in the USA by Burlesque Magazine, so head to Dante’s on a Sunday night to sneak a peek at this sexy and creative show. Tickets start at just $10, so there’s no excuse for missing the sultry circus.
  • “Watching other people dance is great. But where can I go dancing in Portland?” you may wonder. At Dixie Tavern, everyone dances. It’s a dive bar…kind of. It’s a dance club…sort of. It’s a freewheeling, unpretentious hangout where canned beer is king, the cocktails are original, the music is loud, and the bartenders are known to get up and dance, too.
  • It’s not all cabarets and indie bands in Portland—there are traditional dance and hip-hop night clubs in Portland, Oregon, too. Shake is a classic club, with mood lighting, bottle service, and hip-hop and Top 40 hits bumping all night.

Where Should I Stay When Visiting Portland?

Hotels in Portland range from twee boutique spaces to grand old established lodgings, but all of them give you easy access to Portland’s one-of-a-kind neighborhoods:

  • The Pearl District – A neighborhood of converted warehouses, revamped industrial buildings, and refurbished hundred-year-old structures, the Pearl is one of Portland’s hippest and most artsy areas.
  • Hawthorne – Vinyl records, vintage clothes, funky bistros, and a colorful, walkable neighborhood reside in the area around Southeast Hawthorne Boulevard, where la vie boheme is a way of life for locals and visitors alike.
  • Downtown – Bright lights, good food, historic buildings, plentiful shopping, and the always-bustling Pioneer Courthouse Square are the hallmarks of Downtown Portland, where a day of wandering around with a coffee in hand or a night admiring the lights over a glass of pinot noir are equally enjoyable.

Portland’s home-brewed blend of charm, eclecticism, authenticity, and eccentricity makes it a prime spot for a guys’ trip. Gather the troops, book your flights to Portland, and get ready for a bachelor party so unforgettable it might rival the wedding itself.

Visiting Portland Internationally?

Q: What documents does a Canadian need to enter the USA?

A: All you need to bring the party stateside is a passport. Make sure yours is current and valid, and you’ll be all set to enter the USA by car, boat, or plane.

Q: What is the exchange rate of Canadian currency to USD?

A: The exchange rate fluctuates, but the American dollar has held strong for some time. When you convert Canadian money into American currency, you can expect to get about $0.75 American for every Canadian dollar.

Q: What is the legal drinking age in the US?

A: As long as you’re 21 or older, you can partake in as many craft brews and Oregon pinots as you wish—it’s the legal drinking age throughout the United States.

Header image attribution: Via Africa Studio/Shutterstock.com