Oregon Road Trip: Central Oregon

In October 2017 John and I took a road trip across Oregon (our fourth!). We spent a week traveling throughout Portland, the coast, southern Oregon, the Willamette Valley, and central Oregon. These trip recap posts will be organized by region for guidance, in case you want to replicate anything we did on our trip. The map reflects the days traveled, and I will reference what day the pictures/information corresponds to.

OR Map 1

On Day 4 we got up nice and early and hit the road from Medford to our favorite place in Oregon: Sisters!


The drive is about 4 hours and we knew what was on the other side was completely worth it. We’d been to Sisters once before in 2013 and we fell in love with it. We’ve been waiting almost 5 years to go back so this was a real highlight of the trip for us.


We arrived at Five Pine Lodge, our respite for the next two days. Five Pine has little luxury cottages that are absolute perfection.


You’re in the woods and they are rustic looking, but the inside has a spa bathroom with a big huge jacuzzi tub, there are comfy kind-sized beds, robes, a huge flat screen tv, a fireplace, and a back patio. It’s my favorite place to stay in the entire world.


The Five Pine complex is huge and is full of awesome stuff. The main building houses the front desk, bike rentals, movie collection, huge sitting area around a big fireplace, etc.


Also on the grounds is an outdoor pool and deck.


There’s also a brewery, restaurant, and movie house!


Last but not least, Five Pine has their own spa as well, which we went to on Day 5 for a couples massage. It was so relaxing and I never wanted to leave.


We had dinner on Day 4 at the Sisters Saloon & Ranch Grill.


Nachos and burgers – what could be better? But truly, the food was great.


Sisters is nestled in the Deschutes National Forest so you can see mountains from every angle. This is exactly what I think of when I think about Central Oregon: adorable towns, snow capped mountains, lush evergreens and pines. Just perfect.


On Day 5 we took a morning walk from Five Pine to downtown Sisters, which was about a mile.




Downtown Sisters is so quaint and full of cute shops, little bakeries, and small places to eat.


We stumbled upon the Sisters’ Food Truck Garden for lunch. There was only one truck up and running – New Public Cafe – since we were a little late in the season. I got this delicious and healthy bowl full of veggies, tempeh, and beans. It was so good.


To me, Sisters is this tiny little oasis of rest and relaxation, surrounded by beauty. I love Oregon, but there’s so much to see and do, that even on a road trip like this it’s easy to go, go, go without stopping. Sisters is the place where I can pause and be present, and I love that about this town.


On Day 6 we, begrudgingly, left Sisters, vowing to return as soon as humanly possible. We stopped in Suttle Tea on the way out of town and I got this tasty pumpkin chai latte. Perfect for October and very delicious.



About an hour north of Sisters, we stopped in the Detroit Ranger Station in the Willamette National Forest, and checked out the Detroit Dam!


Another hour north we arrived at our touristy stop for the day – Frank Lloyd Wright’s Gordon House in Silverton, Oregon.


The Gordon House is the only Frank Lloyd Wright house in Oregon. It was originally designed in 1957, completed in 1963, and first located 25 miles north of this location in Silverton.


In early 2001 the house was dismantled in pieces and moved to the Oregon Garden, about 20 miles southeast of its original location in Wilsonville.


The Gordon House is part of Wright’s Usonian designs, which were a category of modest, low-cost houses that Wright developed in 1936. The concept was a versatile, standardized house plan that could be adapted to the requirements of Americans of moderate means.


The house features Wright’s classic horizontal designs and a distinct connection between the outdoor and indoor spaces that is amplified by the floor to ceiling windows in almost every single room.


The original kitchen is maintained in its retro style, which I loved. Also kind of obsessed with the dusty rose bathroom.


The living quarters are all on the second floor and were quite modest. This aligns with Wright’s typical design of having bedrooms small in size and on the periphery of his homes, to encourage gathering in the main areas.


We’d only been to one Frank Lloyd Wright house before – the Zimmerman House in New Hampshire – so this was a real treat. I can’t wait to go to more!

We ended Day 6 in Portland so that completed our loop of Oregon on this trip. Click here for my Portland and Greater Portland blog to read all about what we did there!

Author: Domestocrat

I'm a lady who enjoys photography, football, cooking, long drives with the windows down, This American Life, kettlecorn, hot yoga, pop punk, my nephews, my cat Reggie, and my home: Boston.

4 thoughts

  1. This is bringing back memories of Bend, Oregon and Deschutes Brewery (literally the best beer I’ve ever had). I love Oregon!

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