The Oregon Trail Part 1: Portland & Bend

August 4th - 9th, 2021

We flew back to Portland on August 4th to retrieve Destiny and Phoenix from storage, and begin part 2 of the Great American Summer Road Trip! This second half is focused on some of the bigger parks that we plan to spend longer stays in, including Glacier, Yellowstone, The Grand Tetons, The Rockies, and Acadia. We are quite excited for the second half, both to tackle some more big mountains and to be able to relax a bit more. Although I’m sure I will keep Ian busy with all the activities I plan. ;) Returning to Portland and Destiny felt as if we were going back “home,” which was strange, because home is in New Hampshire. However, after 3 weeks of essentially living out of a suitcase, and spending about 5 nights total in our apartment, we were ready for some stability. 

Our three weeks at home (July 15 - August 4) were filled with lots of quality time spent primarily with family, and a few friends. We wish we could have seen more people, but our schedule was jam packed with a wedding, a bachelor party for Ian’s stepbrother - the groom, some hiking on our home turf - the White Mountains, a family vacation with my parents to North Conway, NH, visits to both of Ian’s folks in VT, and two concerts (Chris Stapleton & Billy Strings). I am exhausted just writing out all of that. Lol. Needless to say, coming home to Destiny and all of our belongings felt grounding after such a busy time on the road back home.

We had scheduled Destiny in for some maintenance for her wheel bearings on August 5th, just outside Portland, so decided we’d spend two nights at Hotel Deluxe downtown while she was being serviced. This ended up being a great call, as we were able to explore Portland on foot, and take advantage of some incredible breweries and dining! More on that in the minute… 

We arrived at Curt’s RV Storage on the morning of the 5th to find Destiny and Phoenix looking just like how we’d left them, with the exception of one thing… a disgusting, moldy, fridge and freezer! We had left a few food items, mostly in the freezer, thinking that we had enough propane to keep it running for the time we were gone. We shall never know, as our trailer battery died prior to all the propane being used. With the fridge not functional for goodness knows how long in a heat wave, the smell was absurd and the clean up was one of the nastiest tasks I’ve had to deal with in a while. I know I’ve said this a lot, but life on the road is never boring! 

After cleaning up the mold situation, and getting everything back to working order, we towed Destiny to a local RV shop, about 20 minutes outside Portland, and dropped her off for the night. We continued on to Multnomah Falls, the tallest waterfall in Oregon at roughly 620 feet, for an afternoon hike. The falls were incredibly busy with tourists. Once we got through the main viewing areas, the crowds thinned out, and we enjoyed a lovely forested loop which included several more waterfalls, raw and beautiful. I am loving exploring more of Oregon already! 

After our hike, we refilled our near empty propane tanks at a nearby UHaul, and then headed back into Portland for the later part of the afternoon and evening. It was both of our first times in this city, and we had fun walking around the downtown and Pearl district areas. We realized how long it had been since we wandered aimlessly around a new-to-us city. Definitely pre-covid. Probably in Europe. 

We stopped at a cool brewery for a beer and a snack, and then wandered to the waterfront, with a plan to end up at the well reviewed Farmhouse Kitchen Thai for dinner later that evening. On our way there, we heard house music bumping, followed it, and serendipitously happened upon a Big Lebowski themed bar appropriately named The Big Legrowlski. This is one of Ian’s favorite movies, so that plus a live DJ enticed us to stick around for a few. Ian got a couple brews and I enjoyed a kombucha and a CBD seltzer (so Portland! hehe). This was also the first establishment we’ve come across that has requested our covid vax cards to enter. Signs of what’s to come? We shall see. We’re certainly not against it. 

We hung out at the outdoor bar for an hour or so, and then moved on towards dinner. There was a wait at Farmhouse Kitchen Thai, so we decided to explore the infamous Powell’s City of Books. Portland has a bunch of these used and new bookstores, pretty neat! It was one of the biggest bookshops I’ve ever been in, and we got lost amongst all the isles until we were informed our table was ready. Our dinner was INCREDIBLE. Seriously, the best Thai food we’ve probably ever had! Unique flavors. Fresh, local ingredients. Serious yum! We hadn’t enjoyed a nice dinner out since pre-covid so this felt good, and normal. Post dinner, we headed back to our hotel and crashed, anticipating we would be spending most of the afternoon in Portland the next day. We had found out earlier in the day that Destiny would require more involved maintenance on her wheel bearings than originally anticipated (read: more $$$ and time), so we weren’t sure when she’d be ready.

We had a leisurely morning the next day, and were surprised to get a call from the RV shop as we were preparing to check out of our hotel that Destiny was ready! We picked up some lunch to go from a food truck (more yum!), loaded up the truck, and headed to pick up our “home” and head on to Bend, about a 3.5 hour drive southeast of Portland. 

We had gone back and forth about whether to tack on Bend, as it added about 7 hours of driving to our itinerary. We originally planned to head to the Oregon coast from Portland, as I had a strong desire to experience it and see the infamous Cannon Beach. I also wanted to connect with my good friend from Carlisle, Ashley Bennett, and her wonderful family, who was on vacation there that same week. However, I’d heard lots of good things about Bend, a mountain town with a population of about 90K people. Unfortunately, it was in the total opposite direction of the coast. Dilemma, dilemma, what to do? Ironically enough, a new hiking buddy of mine, who I met while home in NH in July, raved about Bend. Particularly about one of the mountains there that she hiked, South Sister, the third highest peak in Oregon. I looked the hike up on AllTrails (a hiking app we often use to find trails), saw a few pictures of this epic volcano hike. The deal was sealed. We were going to Bend. 

Bend is gorgeous. Full of tall pine trees, the most outdoorsy people you will ever meet, and a super cute downtown that sits perched upon the Deschutes River. We stayed about 5 minutes from downtown Bend, within the city limits, at the no-frills, long-time family owned Scandia RV park. This was probably my least favorite campsite of the trip, as our site looked directly into a Wendy’s parking lot. Talk about nature. But it was super close to Bend which was nice, as we ended up taking advantage of, you guessed it, the delicious food and beer scene there. We pretty much ate our way through Oregon. It’s the most we’ve eaten out this entire trip, but so worth it! After settling into our campsite, we did some more fridge / freezer sanitizing, a shop to restock our food supplies at Fred Meyers, and then grilled some dinner. 

Day 2 in Bend was one for exploring the great outdoors! We had a leisurely morning and decided to head to nearby Newberry National Volcanic Monument to hike Paulina Peak. We chose this hike because it looked unique and also had a good amount of shade, which was a plus given it was a warm, sunny day. At roughly 7 miles and 1600 feet of elevation gain, Paulina was a terrific warm up hike for South Sister, which we badly wanted to climb the next day. The only issue was that this particular trail head was requiring a wilderness permit to complete the hike. Not realizing this, we had missed the boat on getting one. We even tried posting in a Bend Facebook group and contacting local guide companies with no such luck. 

Back to Paulina… the hike was lovely and had some exceptional views of the surrounding mountains. We tried to guess which ones they were. The hike also featured a volcanic caldera and huge lava field, amidst two alpine crater lakes. We learned a lot about the volcanic activity of the region, and noted that we weren’t too far from Crater Lake, where we spent time earlier in July. We could even spot nearby Mt Thielsen, the lightening rod of the cascades. We enjoyed a hummus wrap at the top, and then made our way down, sitting lakeside for a snack and a rinse post hike. 

That evening, we decided to explore downtown Bend and see what all the hype was about. We parked by Deschutes Brewery, our first stop of the evening, for a beer, before taking a 20 minute stroll down the river, eventually landing at Spork for dinner. Everything about that meal was perfection, and we loved how the food was influenced by the owner's international travels.  We walked backed to Phoenix, stuffed, and drove home, deciding we would get up early the next morning and attempt to do South Sister without a permit. We figured we’d try our luck and if we were turned away, we would do another nearby smaller peak instead that didn’t require one. I find when we travel, if something is meant to be, it has a way of working out for us, so we were willing to try. 

We were boots on trail at 7:20am the next day. No ranger in sight checking passes, so we cruised onwards and began our hike. It would take us about 8 hours over 12.5 miles and 5,000 feet of vertical, but it was one of the most magical hikes I’ve ever been on. A top 5 of this trip (so far) for me for sure. The trail wove through huge mossy pine forests, alpine lakes and meadows, and finally, a challenging climb that switchbacked steeply through scree (a new hiking element for us) up to the volcano’s rim. We would meet another young couple at the top, Haley and Michael, who we leapfrogged with over the course of the climb. They were fellow east coasters who were also out road tripping around Oregon for the week, currently staying in Bend and heading to the coast next, just like us. We hiked down with them and exchanged info before departing ways. Ian and Michael had discovered they both shared a love of surfing, and hoped to do such while on the Oregon coast. Would we cross paths again on the coast? Only time would tell. 

We headed back to Destiny, beat from a long day of hiking, but decided to clean up and take advantage of one last night in Bend. We grabbed beers at Bend Brewing Company, which had a nice outdoor area on the river, and then decided to grab Detroit style pan pizza at a local food truck. While there, we met an older gentleman named Brooks, who was passing through Bend on his way to northern Idaho where he owns a property. Brooks raved about Sandpoint, his quaint lakeside town. Coincidentally, or maybe not so, I was looking for a good stopping point in Idaho between Olympic National Park in WA and Glacier National Park in MT, to break up the long drive. I researched RV parks the next day, and ended up booking one right outside Sandpoint for 2 nights. I feel like every person we’ve met on this journey has been for a reason. Many have shared very helpful information with us that has influenced future stops on our trip. This is one of my favorite parts of traveling and I have certainly missed it over the last 18 months. 

After dinner, we headed home and prepared for our departure the following day to the Oregon coast. We were sad to leave Bend. It’s a place we could certainly see ourselves spending more time at some point in the future, as there is so much to explore. I’m very grateful that we ended up taking the time to go out of our way to this special town, and look forward to spending 5 nights exploring the mystical Oregon coast. To be continued… 

For more photos of our time in Portland and Bend, click here.