Best ways to spend your Gaycation in Portland

March 25, 2019

by Cory Kenoyer

Portland may not top the list when it comes to Gaycations in the United States of America, but it should be somewhere on there. PDX is a fine little city, where we love our visitors and tourists and all your fresh, beautiful faces. For those new to traveling Oregon or the Pacific Northwest in general, we have the pleasure of experience all four seasons around here so come at a time that best fits yours (and hers/his) preferred kind of climate. Maybe you’re just here for a little while or maybe a longer stay, either way here are some LGBT+ places around Portland, and other spots worth a visit depending on when you come.


Boy howdy do we start missing the sun during winter, fall, and spring. Portland does deserve the stereotype of a cloudy, rain-drenched city, but when summer hits you can expect temperatures to sit well within the 90s and 100s. When the sun starts blazing, we gays start emerging from our nests, our gyms, and start working on our tans, and adding “hiking” and “outdoors” to our Grindr profiles. All sass aside, one of the best times to see some natural splendor, is during the months of June, July, August.

Rooster Rock

A state park with clothing-optional and clothing-required beaches along the Columbia River, Rooster’s is the best beach to give those places where the sun don’t shine their due diligence. Right off the parking lot is a short walk to the riverbank designated for swimwear, and a bit father (quite a bit farther) of a walk is for a more casual look. Make sure to show up early so you can claim a spot, it can get pretty crowded as the day grows long.


Pride month in Portland! A time when a notoriously accepting city gets even more accepting. Along the Waterfront Park, there will be booths, concerts, and activities celebrating pride. The Gay Mans Chorus takes to the Arlene Schnitzer concert hall, and a Gaylabration at the renowned music venue at the Crystal Ballroom. June is also home to the Naked Bike Ride for those who want to bike around the city in the buff, maybe after rooster rock!


The Big Float is a giant flotilla of river-goers marching through the city with innertubes, cleaning up the beach, watching synchronized swimmers, and watching live music on a giant barge. Prizes are awarded to those with the weirdest, wildest, watercraft and costumes, and it’s a hilarious way to beat the heat in the month of July.

Experience those Autumn Colors

Summer is too hot for most hikes (except for Oneonta Falls, where you ford through a stream) but come Autumn when the temperature drops from the 90s to the 60s and all you need some light outerwear for the sweater-weather—Magic. No joke when I say Fall is my favorite season once the colors start to change and all the hikes in Portland open up. This one has an all-year-round tip too: Ramen Ciro.

Washington Park

First thing’s first, get some ramen to-go from Ramen Ciro, either the PSU location or the one on 3rd and Washington. Easily some of the best noodles and broth in Portland, this downtown food carts worth a visit and will warm you up. Next thing’s next, head to Washington Park. A rather large park, it’s home to the Hoyt Arboretum, the Portland Rose and Japanese Gardens, and the Pittock Mansion. During the summer you can also catch the free and family-friendly variety show Peacock in the Park: Portland’s gay equivalent of the Super Bowl. The botanical variety is romantic for those looking for a cute walk, and you can def get some IG photos at the many, many views spread around the park.

Spending time indoors during wintertime!

My friend recently explained to me what “cuffing” was and that Winter is “cuffing season”. You and a friend, or beau, or whichever label you two ascribe to partner up during the winter and do all the loving stuffBFs/GFsdo during those long frigged months. Never had I felt so estranged from my queer, millennial cohort. Like what happens when one partner wants to continue while the other is ready to say “see ya!”? Well, that’s for another article, but for those of who are cuffed or single one of the best ways to spend winter is indoors, so come inside and sit a spell or dance at…


The newest all-genders welcome dance club in town routinely hosts drag shows, and other queer-centric events, as well as great DJs, two dance floors, and tall AF ceilings giving it a warehouse aesthetic. Second Sundays are dedicated to Women-loving women.


A nice bar to visit any time of the year, but on Tuesdays and Sundays especially you have some of the greatest Karaoke singers in town belting out ballads and hits. Nice outdoor, sidewalk-facing seating area you can bring your drinks out to all-year-round.


A laid-back corner bar on the east-side, Crush has friendly bartenders, great food with vegetarian options, and I’m a personal fan of the music rotation. You could say it has a hipster vibe, but what Portland bar doesn’t.


An E-Sports bar for all those Gamers out there. It opened up in October 2018 with gaming PCs, Nintendo and Sony game systems completely open for use after the purchase of a drink or food. I come here by myself or with friends after work and can always find a group for Smash Bros. at a TV, or find a PC for HoTS. A large up-to-date game library is available to accommodate everyone.

And finally, that fresh spring air!

Dining Month

The month of March is Portland Dining Month here in PDX, where over 100 restaurants serve special three-course meals for only $33. We’re a city of foodies, and this is a particular spring activity for fellow culinary tourists to try some of the greatest dishes we have to offer without breaking the bank. Try a new restaurant every night your here, from Ethiopian to Cuban to Italian.

POWfest (Portland Oregon’s Women film festival)

Also in the month of March is a festival showcasing films by honoring the true pioneers and recognizing the next generation of leading women, and non-binary filmmakers. There are workshops for girls, and non-binary youths to help inspire and strengthen the Portland Community.

Red Dress Party

Held in early May, Red Dress is an event that brings in almost 2,000 LGBT+ people all dressed in red dresses for a huge underground party. Last year the organization (run entirely by volunteers) raised over $30,000 for the LGBTQ community here in Portland. If you are planning your trip around the month of May, buy a ticket, bring your pumps and red gowns, and enjoy a truly memorable event.

In finality,

Portland, Oregon has a lot of great activities to offer for the gaycationers. Way more than I could write about in this article, to be fair. Hopefully, something in this travel piece persuaded you to come to my fair little city— at any time of the year. Please feel free to contact me directly if you need any more suggestions down the road as your trip draws nearer. And for any straight allies reading this article, these are activities and suggestions you are more than encouraged to join in as well. Portland is a welcoming place, and we would love to have everyone.

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