Why We Keep Returning to Epically Gay Portland, Oregon Again and Again

There’s lots of beautiful things to see in Portland, Oregon

A city that keeps growing on me every time I visit is Portland, Oregon. This past March, I was able to visit the city for an extended period and took that opportunity to explore more than I had ever done before.

The city itself is a great hub of the Pacific Northwest, allowing you to go east into the picturesque nature of Oregon along the Columbia River and through the Columbia River Gorge, north into Washington State, south to wonderful wine country in the Willamette Valley, and West to the Pacific Coast. But… if you want to see Oregon’s nature, wine country, and the city life, there’s no need to rent a car and leave the city, it’s all right there without leaving the city.

The Nature –

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It was early March when I visited Portland this year, holding over in this west coast city just after Hood River Pride. For that time of year I was experiencing a warm spell in the 50s and 60s. One of the first things that comes to mind when I think of Oregon is GREEN. They have so many shades of natural greens, blue-greens, grey-greens, green greens, and fluorescent green.

My previous Portland visits had kept me to the flat downtown areas, but little did I know, there was so much vibrance in the near hills to the west. It was the wrong time of year to visit the International Rose Test Garden which will be on my list for my next visit. Right next to the Rose Test Garden is the Portland Japanese Garden. The rideshare from downtown to the gardens and then to the zoo brought you through some amazing hills, twists and turns, over abandoned rail trails, and from Arlington Heights and Washington Park, you could see across the city and for miles beyond.

 
 
 
 
 
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Hours more could have been spent soaking in the beauty, simplicity, elegance, intricacies, sounds, and emotions seen and experienced while spiritually flowing through the Portland Japanese Garden. Definitely place this gem of a destination on your must-see list when you visit.

The Oregon Zoo was next on my list to visit while up in the hills. Once again, the ride there was half of the pleasure. The zoo was well maintained, well designed, and well respected by the visitors. I did have a hard time se4eing the elephants in captivity after seeing them in the wild in Thailand, but it was a beautiful day to see all the animals enjoying the weather, even though the bears seem to be still slightly hibernating.

Wine Country –

There are many wineries and cider houses just on the outskirts of the city. Without a car, I used a rideshare app, selecting the comfort option to make sure they would travel the distance to drop me off and pick me up.

Ponzi Vineyards was my destination for a wine lunch or was it for lunch with wine? It was a 3-course lunch with epic views, full-bodied potations, and a curated menu that was saddling winter and spring offerings. We had a chance to talk with the chef about his experiences and his drive to prepare such a menu that paired oh so well with the Ponzi wine offerings. 

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19 Acres Cider – I was pretty full and feeling fine from the Ponzi wines and 3-course meal, but looking at the map, I pondered, when will I be out in this area again, and I found a nearby cider house – 19 Acres Cider. It was a quiet place until one of the owners came in with some friends and gave them a tour of the property.  I folded myself into the comfy couches, watched the amazingly cute boy prepare me a pretzel, beer cheese dip, and gherkins to ingest while I sipped the ciders they had to offer. It was a beyond comfortable environment, very tasty food and ciders, overall, a great relaxing experience part 2 for the day. Yes, I fell asleep in the rideshare back to town.

Portland ‘s Gay and City Life –

Portland has been one of my more fun cities to visit, especially the night life. Yes, I like to dance and go to clubs, but the nightclubs in Portland charge covers so I usually don’t go (Badlands, CC Slaughters). I’d rather go to one of the handful of strip clubs and give that cover charge to a dancer to uncover. Yes, those clubs also do charge covers but not always and I find that cover worth it. The Stag PDX is my first choice, but I also did go to Silverado. I much liked the old Silverado location better as the dancers were more front and center and not down in the basement performing on a stage where if they did a great maneuver on the pole, they may slam their head into a fixed table.

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The variety of dancers at both clubs was nice but has changed recently. The Stag PDX used to have transgender female, but within the past year, something happened and they are now dancing at the gentleman’s bar for “straight” men go. The Silverado had some beefy guys, some soft guys, and one pairing of tall sleek muscular black flamboyant men.  All of it was entertaining, chatting with them all was great, no lap dances were had, but some good strong drinks and some great eye candy.

Darcelle’s – Darcelle XV Showplace – It’s always fun to go here, too. The entertainers have a great deal more clothes that the places mentioned above as this is THE drag spot to go to in Portland. We did the drag brunch for this visit which had some old and new talent, and new owners since our last visit.

 
 
 
 
 
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I did go to Scandals, like I do during every visit. It’s a downtown bar with a local neighborhood bar feel, but I still have not had an amazing time there. It seems more of a great place to catch up with friends, not to make them, maybe it’s just me. The tap beer selection is small but solid, the gambling / slot machine corner is a little confusing for this out of towner, and the seating is fine, but presents itself more restaurant style and not “come in, sit down, and socialize”.  I’ll keep coming back here and giving Scandals a try as it is one of if not the only remaining gay bar on the very historically gay Stark Street, now called Harvey Milk Street.

Any Bar / Brewery – Downtown Portland, especially the Pearl District, has many several spots to stop in and have a beer, a flight, or both or many of each. And you will never know who you will meet. Nick, thanks for the chat, probably one of the best chat’s I’ve had out in years. Over beer, good food, and some basketball on tv.

My own private terrace at teh Sentinel Hotel

Lodging – Sentinel Hotel – 

The choice to stay at the Sentinel Hotel downtown was the perfect choice. Sentinel was named one of 2024’s Top 10 Best Hotels in the Pacific Northwest by readers of Condé Nast Traveler. Visiting the hotel’s website, I picked out the luxurious and spacious Terrace Studio Suite. The workspace table was massive, chairs comfy, bed cloud-like, and private terrace with 2 couches, gas fire pit/table, and string lights overlooking the city. 

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Just blocks from Harvey Milk Street, one more block from Burnside Street and then the Pearl District, the Sentinel Hotel’s location was perfect for me to easily walk to everything, even the always fulfilling Portland Saturday Market. 

And if one doesn’t want to leave the hotel, there was an attached restaurant, happy hour in the lobby with free wine, a special snack and beverage lounge for just people on the top floor, and the hotel bar that was THE place to be downtown for a nightlife.

How Is The City of Roses Doing?

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While I was downtown and was visiting businesses, hotels, shops, touristy spots, I asked the question, “How is Portland doing?” We all saw some of the events during the pandemic and Black Lives Matter that really affected Portland and put Portland in the spotlight for one of the cities of our nation that had gone through some changes and hardships because of those two very historic events /time frames.

The hotels were doing well, getting back up to speed but not to the levels of pre pandemic and pre black lives matter. Some of the stores downtown were still recovering, most of them were looking good and looking great very clean spaces windows repaired, but some of the larger stores, some of the jewelry stores, they had commented that they were not up to the pre levels yet. They had restocked as much as they could, mainly the basics, and have not looked at anything more than that at this time.

But one thing I did do was I looked up more this trip. I had always had my mind that Portland was a grey city may it be because of the weather, but I’ve also loved the greenery of Oregon as a whole period but staying downtown where I did I did notice that the architecture was not plain, it was vibrant, there were murals around town. People were taking responsibility for their spaces and showing pride in their spaces so that was nice to see. But I think as a whole talking to most people they were happy to be at the spot they were at this time but they were looking forward to doing bigger and better as time went on, they were happy for the recovery but looking forward to what is yet to be.

And knowing that Portland is getting better and is at a good even keel point as a city, things should be on the mend, have mended, and then some, it just makes me happy to revisit the city in the future to see that it has returned to the vibrant and pleasing city that I experienced on my first visit.

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