Chad C.
Yelp
I've always lived within the vicinity of Portland and have never been here. I knew that it was old, and expensive, and also a ski resort, so coming here in late September (the very tail end of the off season) I had no idea what to expect. I've also stayed in historic buildings before with wildly mixed results. So, when I told my mom I was going to spend the weekend at Timberline for my friends wedding...well, I just don't know how to convey the tone of her reply. "Timberline!?"
The drive here is astounding, but be prepared for the effects of the elevation change, both on your body and on your car. You really are high enough up for your car to lose a little power, not to mention your own capability to haul your luggage (or just yourself) around. But once you get past that, the lodge is truly remarkable inside and out.
It's a bit easy to get lost in the building, as it's sort of a split level design from one wing to a other. On the ground floor you'll find two media rooms, a museum (that is staffed with forestry service personnel) and the front desk for the hotel. There is an elevator for when you feel like your lungs just won't work anymore.
The rooms are relatively close to what you would have found in the '30s (1930s, that is). No air conditioning (you'll find fans, space heaters, and window screens in the closet), but the rooms all have electric light, a couple electric outlets, and a television. Some rooms are a bit odd (there are bunk style rooms that are like dorms, sharing a bathroom down the hall) or may actually have bunk beds in them, or the bathroom will be split between the toilet area and the shower, and some have fireplaces. So, you'll likely want to try to find a room on the north side of the building in order to avoid massive temperature swings through the day and night.
The bathrooms are a bit institutional, with a pressure toilet and wall sink. The beds were super comfortable with plenty of pillows and soft, not starched and scratchy, sheets. The TV is high def/flat panel, and is connected to...some kind of cable or satellite situation.
The walls are thin here. You're going to hear your neighbors a bit, and people walking up and down the halls, and when there are air pressure changes in the building, your door will rattle a bit. Quiet hours are posted everywhere and are fairly strictly enforced. Despite this, the silence at night is positively serene.
Where this place makes up for the various pitfalls of a historic building, it makes up for in spectacular surroundings and service. All the on-site restaurants are delicious (if not on the spendy side), the staff are beyond wonderful and genuinely want you to have a fantastic stay. The pool, hot tub, and sauna areas are fantastically maintained. Want to watch "The Shining"? They can set that up in a shared media room for you. Want to set foot on the PCT and brag to your friends? It's just outside your door. In the winter, you're literally footsteps from multiple ski lifts and runs, and each room includes a ski locker at the entrance.
Regardless, this is a unique resort that you'll definitely enjoy regardless of the time of year, and is all of a 1.5 hour drive from Portland. If you haven't done it before, take a room here as it's an experience you'll never forget.