The Benson was an absolute win on my first ever trip to Portland.
From the second I pulled up, the experience was easy. Valet was smooth, there was plenty of room to arrive without feeling like you were trying to find a place to squeez in, and the valet team was consistently kind, accommodating, and quick both on arrival and whenever I needed my car.
The hotel itself is gorgeous. Not fake-luxury gorgeous. Real, classic, old-school gorgeous. The kind of place that makes you stop for a second when you walk into the lobby and think, "Wow!" The architecture and design have that turn-of-the-century grandeur that feels rich and elegant without being stuffy. The lobby in particular is one of the most impressive I have seen anywhere - dramatic ceilings, beautiful woodwork, and a mirror fit for a French King.
Check-in was simple and painless. My room was spacious, comfortable, and had one of those beds where you lie down and immediately question what the heck kind of mattress is this, and where can I get one. I also had a large executive desk, which made it a genuinely cozy and functional place to get some work done.
The gym was another pleasant surprise - and not one of those “fitness center” situations where they give you a treadmill, two dumbbells, and a broken water mater. This was a real gym. Big, well-equipped, lots of room, and even two Pelotons.
But the real highlight of the stay was the staff, especially Tara at the bar.
On my first night, I was still running on East Coast time and had some time to kill before dinner with friends, so I grabbed a seat at the beautiful bar and just wanted a quick bite. Instead, I got a genuinely memorable experience. Tara was warm, funny, welcoming, and one of those people who instantly makes a place feel better. We ended up chatting about Portland, Irish dancing, and the history of the hotel. Another night, she recommended dinner for me and every single suggestion landed - appetizer, entree, bread pudding, all of it. Easy 'clean plate club' FTW.
Breakfast also deserves a mention. Try the yogurt and fruit. That sounds like an aggressively boring recommendation until you eat it and realize the fruit is somehow perfect.
The neighborhood was great too. Easy walking distance to all kinds of excellent spots, including Maurice (Small hole-in-the-wall French place you'll be blown away by) and Powell’s, the world's largest bookstore, is basically right there too.
All in, I loved my stay at The Benson. Beautiful hotel, great location, excellent amenities, and a staff that knows how to make a place feel special. I would happily stay there again.
