First of all, congratulations! When I opened this email, I got goosebumps and butterflies and my heart started racing and I immediately had a million ideas in my mind of where you should go.
But first. I’m going to give you my top 5 favorite places in each of those three locations. And then I’m going to give you a list of wineries to look at, too.
Here is an ambitious itinerary that is also doable without feeling like you’re constantly on the go:
Day 1: Crater Lake
Campground: Lost Creek Campground
You can stay here without feeling like you’re in a box of sardines. It’s my favorite campsite in the area and doesn’t have a lot of people. Also, the Pacific Crest Trail is accessible here and you can take a short walk/hike to the Pinnacles in the area. It’s not far from the rim of the lake, but it’s not overlooking the lake. It’s also a first-come, first-serve campground, so if you can snag a spot, this would be an ideal place to pop the question.
Another option for a campsite would be Diamond Lake. It’s just 12 miles north of the rim and there are significantly LESS people there. So after a day of exploring Crater Lake it might be nice to settle down near another ridiculously beautiful lake with an epic view of Mt. Thielsen.
One thing to keep in mind: Sometimes the rim road is closed to cars and only accessible by bike. Keep that in mind and maybe double check the weekend you’re planning on coming out.
Day 2: Hot Springs
A must-see attraction is the Umpqua Hot Springs. You’ve gotta do it.
You can still get your hike to Tokatee Falls in, and you should, because it’s awesome. But make sure you spare an hour or two to check out these natural hot springs! This wouldn’t be the worst place to propose.
Day 3: Bend
I love Bend. Everyone loves Bend. It’s true. You’ll love it, too, I promise.
By then, a shower and fireplace will probably be welcomed and there’s also so much more to do there! If you haven’t proposed yet, check out Tumalo Falls, it might be what you’re looking for. Crux Fermentation Project, McMenimans, and Rogue Brewery are all really great places to celebrate as well. Honestly, Bend has more beer than anywhere else you’ll ever go in your life. Except maybe Germany. But that’s up for debate. You could rent bikes and ride along the Deschutes River Trail or go for a run along it. You could also hike Pilot Butte, take a scenic drive along the Cascade Lakes Scenic byway (it’ll drop your jaw), there are lava lands outside of the Newberry National Volcanic Monument, Mt. Bachelor is pretty incredible, too.
Day 4: Smith Rock
Mmmm, Smith Rock. One of my all-time favorite places.
So, you can’t actually ‘hike’ Monkey Face. But you CAN see it from the hike called ‘Misery Ridge.’ It’s not that bad of a hike. I was able to do it two weeks after having ACL surgery last spring. This hike offers the best views, the best elevation gain and the best bang for your buck in the area if you’re going to hike. You get to experience everything Smith Rock has to offer.
If you decide that you want to climb, I’d suggest Five Gallon Buckets. It’s a popular route but it’s easy and is the best route for gym-climbers to get comfortable climbing outside. If you want to climb Monkey Face, I’d suggest getting here early an expecting a bit of a wait before roping in for this multi-pitch. It takes awhile, but it’s worth it.
If you’re looking for campsites in this area, there’s the climber’s bivvy. But it might be filled with loud climbers scrounging for leftovers. Skulls Hollow is another site that’s not too far from Smith Rock but I would highly, highly recommend camping at Haystack Reservoir. If you can get a spot by the water, you get an excellent view of Mt. Jefferson and sometimes, when the sky is clear enough, the stars reflect onto the water and it is the most amazing thing.
Day 5: Hood River
Alright, Hood River is cool. I wish I could tell you it was worth skipping but if you did skip it, I’d be offended I think. And I think you’d regret it. On your way from Bend to Hood River, there’s a hike called Tamanawas Falls. The pull-off is on the left-hand side of the road. It’s four miles round trip and is easy, fun and the payoff is totally worth it. When you’re done doing that… there’s an awesome little coffee shop in Hood River called Doppio’s. There are sandwiches, soup and some of the best coffee, ever.
If you’re still thinking about mountain biking, check out Discover Bicycles. They rent bikes for $60/day and give you helmets, maps, directions, etc. Everything you could ever need or hope for. Check out Surveyor’s Ridge for the mountain bike ride. It’s relatively easy and follows a ribbon of single track through the trees, down valleys and opens up to incredible views of both Mt. Hood and Mt. Adams.
But if you don’t want to mountain bike… take a drive along the Fruit Loop! Depending on the time of year, there are U-pick flower fields, u-pick fruit and vegetable fields and (!) wineries. Mt. Hood Winery is a great place to stop with a great view of the north side of Hood. You should be able to see Mt. Adams from here, as well.
At this point, you’ll probably be exhausted. You’ll probably be love drunk. And you’ll probably be looking for houses to rent or buy and planning on moving to Oregon.
But you should actually start driving toward Portland. Because you’re almost out of time. Get some more coffee.
You’re going to pass the Columbia River Gorge, on your left. Once you hit Cascade Locks, take the exit to get onto the Columbia Gorge Scenic Highway. This road will pull you past handfuls of waterfalls and lush, natural rainforest. There will be plenty of places to pull over, get out, hike up to and take a ton of pictures in front of some really awesome falls. My favorite is Elowah Falls. It’s a short hike in, but whoah. It’s worth it.
Multnomah Falls is by far the busiest area of the Gorge, but once you see it, you’ll know why. (It’s also the waterfall from Twilight, just a heads up). This waterfall comes with it’s own parking area and lodge. There are a handful of other falls to see along the way, too, so save your neck muscles and don’t spend too much time looking up.
I’d suggest staying somewhere in Portland this night. Especially if you’re going to fly back the next day. But if not, take your time! There are plenty of places to see and things to do and you might want to try stopping at every waterfall. Who knows?!
I hope you guys have the best trip. I’m so excited for you!