Jeepin' Through Oregon!


When you read this story, always keep in mind that I have a tendency to break off into tangents.. so forgive me now!

I'll keep this part simple. This all started back in November 2017 when Southwest Airlines was having their $54 one-way fares to locations around the US. I saw the Ad several times, and continued to scroll. But then there was that one time... that one time you get a quick idea in your head, like "what if... I went to Denver." Or, "what if I went to San Diego.." (since I’ve never been). I tend to do this often. I love to look up destinations, map out fun journeys, and check out unique restaurants and hole-in-the-wall eateries. Maybe one day I could become a food blogger and run around cities inhaling the tacos from food trucks -- Calm yourself, Megan, you're getting ahead of yourself already. Alright so it all started with the 'what if' moment. I clicked the Ad, went to the drop down menu and scrolled to see what options I had. I mean, let's be real, there's maybe a good 3 to 4 cities on there that caught my attention. But for some reason, I was attracted to the idea of going into Portland.

I want to say it was the combo of wanting to get-away (see what I did there Southwest, wink) and the fact my youngest sister just started college at OSU - so why not, right?

Checked my calendar. Winter season for me lasts until end of February... so boom. February 8-12th it was. I booked my flight with Conrad (the bf) for $107 total (each) round-trip, and put it in the calendar. It was set. 

Two months pass..... and I barely had plans laid out. Confession: A good two weeks before we flew out, I started to actually get my butt in gear and started planning out our trip. Now, let me tell you: BEFORE we got to Portland, I had mapped out several AirBnB locations, hotels, and VRBO options for us to stay at nightly. However, this completely shifted upon arrival to Portland Airport (PDX).  

Courtesy of  MapQuest

Courtesy of MapQuest

So there it is. Our five day, four night travel route through the western side of Oregon. I started Yelp'ing food options, breweries, places to see. I checked other bloggers pages, looked at people's recommendations for low-key spots. I did some hardcore researching, let me tell ya. 



We landed in Portland around 1:00pm on Thursday. Pilot was generous enough to let us know that it was cloudy and 44, so it was apparently nice day. Let's be realistic, in California, as most of us know - 44 degrees is a chilly night in the winter. So it was a different type of cold outside here in Portland!

Conrad and I, mid-flight

Conrad and I, mid-flight

We grabbed our bags and head over to Enterprise where I had reserved us a "Standard" vehicle for the drive. After jumping through a couple hoops, I gave the attendant my card for payment, and he says "USAA, huh? Did you book us through them?" 

"....No, actually I booked you through your site." 

"Oh honey, I'm going to cancel this reservation for you, trust me, go take a seat and reserve us again through USAA. I promise it will be worth it," he was so confident, so of course I did it. 

Around 10 minutes later I finished and went back to him with my card for payment and a new reservation number. He pulls up the account and sure enough, we saved over $60 and upgraded to a larger "Full Size" vehicle. He processes our paperwork and sends us upstairs where the cars are. We got lucky enough to meet someone who showed us to our nice Cadillac.. something. It looked like a nice car! But then she asked us what we were doing in Portland, and I told her about our fun half-planned full circle that we're about to do. She informs us that "if we're going to be hitting the National Forests and Crater Lake, we should consider a 4x4 vehicle" and points to a gorgeous new(er) charcoal gray Jeep Grand Cherokee Laredo. I was so sold. We upgraded again (for only $80 more the whole weekend), jumped in the car and took off. As we hit the road to Tillamook, Conrad and I fell in love with the car, and quickly realized the size of this beast. We could definitely camp out of it if we wanted.... 

So we pondered and thought about it - within seconds we agreed it would be so worth it! 

The road to nowhere...

The road to nowhere...

I started as driver of the journey for the first leg of the trip. We followed our map and went straight for Tillamook to make sure we get to the Cheese Factory before they close (which was actually not until 6pm, we had plenty of time). 

About halfway into the trip, we came across this nice pull-over area in the Tillamook National Forest where people could stop and stretch, take pictures, whatever. I chose to pull off because it looked like there was this road on the side of the parking area that could maybe lead us to some cool viewpoint. I started driving up the road, further and further into the clouds, and smaller the road. First off, the potholes in this road were craters. MASSIVE holes - I should have just turned back then. But nope, that's not very normal of me. I kept driving further and further.. and the road got smaller and smaller..


Fortunately nothing crazy happened. Unfortunately, this road was super slick from the mud, so I had to do a 6-point turn to make sure we didn't slide off the side of the hill. Obviously I didn't (because I'm a damn good driver) so we went back down the path and got back on the main road. Come to find out it was in fact not a road, it's a hiking path that I just drove up. So no cool viewpoint this time.

<--- Oops. 

Hey what's a good adventure without a little detour, huh!? ;) We carried on and finally landed at our destination. 


The Tillamook Cheese Factory


My recommendation: TRY THE GRILLED CHEESE and dip that amazingness into their tomato soup. Ohhhhh-em-gee #noregrets people! BEST I've had yet! We ate at their cafe, then went over and shopped at their cheese store. We learned how cows make milk.. and a little bit about how cheese is created. We left there with a bag of Colby Jack Tillamoo's and a block of medium cheddar. Yum yum yum.

Oh and before we hit the road to our next stop... I got me a picture in the Tillamook Cheese Bus... 



The next stop on the itinerary was a Brewery just minutes from the cheese factory: Pelican Brewery. We stopped in for a couple of their beers, and an awesome chat with the bartender who gave us a great tips on places to see while we're in Oregon! 

After that, we cruised down highway 101 until the sun was no longer visible. It was already a cloudy day, so it was a quick sunset on day one! 

We then cut across Siskiyou National Forest to close out our night in Salem, Oregon - the state's capital. We got into town around 7 or 8pm, so we drove around to see what we could do in a big city up here. Thanks to my handy Yelp App, I came across this little place called The Victory Club in downtown. It took us a good 10 minutes to even find it, and we were very close to letting that one go to find something easier! But luckily the security guy on duty that night took the long route to the bathrooms and ran into us. He asked if we were lost (because I clearly probably looked it) and then guide us to the Victory Club. Yayyy success! I ordered whatever beer the bartender recommended (which btw: I couldn't tell you a single beer that I drank on this trip - sorry) and also 2 chicken tacos to settle my hungry belly! Delicious! Nothing short of satisfied! We also happened to hit this place on Thursday night Karaoke - so we had some awesome entertainment as well! 

After filling up on yummies, we head out to a local 24 hour fitness to clean up and prep for our first night on the road. If ever a time that my gym membership came in handy - it was this time. 


We woke up in Salem around 7 am to start the next leg of the journey. Today was the day I get to see my youngest sister at Oregon State University, and then we planned on driving up to Crater Lake around sunset. So we hit the road after grabbing that morning coffee. The distance from Salem to Corvallis is actually quite short - 45 minutes-ish. Though I believe it would be shorter if the speed limit on the freeway was 65.. or 70 mph (it was always fluctuating between 50 - 65 mph). It's a much slower lifestyle outside of the Bay Area, and it's funny how surprised we all get when we're forced to slowwww downnn a bit. 

Anyways, we got into Corvallis around 10:45 am and toured ourselves through the town and school to see what it was all about. It was a very cute town with a lot of brick housing (which I LOVE!). We met my sister, Melly, around noon, after her class was out. Touring her dorm room was awesome, but the Chi Omega sorority she's in, was WAY cool! The girls have such a beautiful house with so much space! Really made me reminisce on the good days... not really, but it reminded me of those days I used to party at SJSU! Good times, friends, good times! After walking the school, we went and ate at this common spot (which we saw in basically every city) called McMenamin's


After grubbing and relaxing a bit, we hit the road for our next adventure: Crater Lake. I was SO excited to get there. It honestly took us somewhere between 3-4 hours to get into the mountain that the lake is on. But this is also where things got a little… unexpected!

Sun had just set and the roads were very dark. Not paying attention to the road closures - we head straight for the North Gate entrance in hopes we could make it to Rim Village for our overnight stay. I had this whole idea in my head that we could camp overnight at Rim Village, then wake up and hike the Lake at sunrise. Nope. Not tonight at least! As we turned left at the road leading to Rim Village (the Northern gate entrance), we slammed on our breaks as we noticed.. the gate was closed, and the snow had not been plowed AT ALL on this road. There was absolutely no way we were getting to the Lake this way.


With NO service, I looked at my handy paper map and calculated it would take us maybe another hour and half to get allll the way around the lake to the South entrance. At this point, it was super late and we were completely unsure with what to do. However… I was not leaving without seeing Crater Lake!

We drove around 10 miles backwards and slept overnight at a small rest stop that we had seen on the road.


Even though it was maybe 12 degrees outside when we woke up - we still made our trek up to the Lake.


We drove the hour and a half around the Lake to the Southern entrance and made it to the top of Crater Lake before they opened the property up to tourists. It was unreal. The air was so cold and made it extremely hard to breath. Wind was a whopping 30 mph up there, and winter was definitely in full swing! But we still did it (taking breaks to go back to the car to avoid freezing).

Conrad even resort to some socks as gloves because it was too cold to look for his other gloves. (see below!)


After taking a handful of photos and freezing while stomping through the snow, we finally head out to get to our next destination: Bend, Oregon. It honestly took a good 15 minutes for my fingers to gain some feeling again. But that’s okay :) Worth itttt!

This was when we started making random stops at random locations along the road, just so we can get a feel for the nature out there! We stopped at this little view that overlooked a river, which was really neat!


Once in the town of Bend, we hit up the first food spot that caught our attention on Yelp, called Bangers & Brews. We were so hungry!

What did I have? You got it - an total Banger… and a local Brew. :)


We cruised through Bend for a little bit, hitting up some local spots and enjoying the gorgeous (much warmer) weather after being at Crater Lake all day. Then when the time was right, we hit the road again, and hoped to make it to Mt. Hood National Forest around sunset. Which… we almost did!

We instead got to see the sun set behind Mt. Hood as we got closer, and boyyyy was that a sight to see! Instead, we pulled over and watched this insane orange and pink sunset behind the snow-covered Mt Hood, and then continued the journey after.


After a climbing through the Mt. Hood National Forest, we decided to stop at a little lodge in the mountain and sleep overnight in the parking lot till morning. Another longgg chilly night!


We woke up and head straight through the other side of the hill so we could go chase waterfalls down the Columbia River Gorge. This.. was.. SO FUN! We looked up all the biggest waterfalls, then hiked to each of them - making sure to capture a polaroid and a backpack pin to show our successes!

We then crossed over the Bridge of the Gods into Washington so we could cruise along the Gorge into Vancouver.

With one night left on this trip, we ended up going into Portland for our last night, and basically stalked every block for the taco trucks, and local favorites. We agreed to spend our remaining fund (from the trip) on tons of small bites and brews that Portland had to offer. I was so stuffed!



Well.. after all that food, we literally slept as if we were comatose. But I have to admit again.. it was totally worth it! We ordered small portions of different foods that way we could try more and more! But as you can see in several of my selfies, I was exhausted and happy to be heading home.

Before our flight at 1pm, we took a drive through Portland to check out the beautiful housing, structures, and parks. We ended up at the view that overlook the entire city. Then we head over to the Airport.. dropped off my favorite rental car, and flew back to San Jose.

Total trip miles driven: 1,081

I highly recommend this trip to anyone!