We traveled to Oregon for a wedding and didn’t have the highest expectations, but were absolutely blown away by the state. Portland has a cool, hipster vibe but also is within an easy drive’s distance to mountains, so it offers the best of both worlds.
Read on for the ultimate travel guide, and don’t forget to check out our write ups of Oregon’s wine valley and where to stay in Willamette Valley.
Day 1:
Hike Mount Hood: Before driving to Portland from Willamette, we took a little detour to Mount Hood for some mountain air and a hike. This was truly one of the (many) highlights of our trip, and something we can’t recommend enough.
This scenic mountain range has hikes of every length and intensity level. We wanted to get to Portland, so we did a shorter hike at around 1.5 hours, but it still offered stunning views and built up a bit of a sweat.
Added bonus — there is a lodge at Mount Hood called Timberline Lodge that is a great place to get a drink at the mountain. Fun fact: it is where the shining was filmed, so be sure to sneak upstairs to the rooms to walk the hall where those infamous creepy twins were filmed!
Biketown: The best way to see Portland is by bike. So, sign yourself up for a Biketown bike pass, similar to New York’s Citibikes, and get going. These ones are run by Nike, which is based in Oregon.
Pearl District: Ride your bike over to the Pearl District, which is a hipster/yuppy part of town with great shops, restaurants and bars. We loved Tanner Springs park. It’s also a great area to get a view of one of Portland’s many bridges.
Powell’s City of Books: This bookstore is the world’s largest independent bookstore and it instantly became my happy place. You can spend hours here perusing their books which range from mainstream to super niche and antique. They also have a killer children’s section where I got my nephew a picture book he hasn’t put down. If you are a book lover, this truly is paradise. Can’t recommend Powell’s enough!
Cartlandia: Next, head to “Cartlandia” for a casual lunch. This parking lot in downtown is converted into an open-air food court of sorts with tons of great food carts. You can get everything from triple-decker grilled cheeses to Korean bbq for a quick bite at a reasonable price. We had a grilled cheese burger at a cart called Grilled Cheese Grill, but if you go, we highly recommend it. The “bun” is two grilled cheese sandwiches with a hamburger in between!
Dinner and Drinks at Basecamp: Head to this brewery for some beers and eats for a quintessentially Portland experience. We sat in the outdoor area which had strung edison bulbs sampling their various beers and local rose.
Day 2:
International Rose Test Garden: Get up nice and early and check those Biketown bikes out again for a day hitting the pavement in Portland. Start with their International Rose Test Garden in Washington Park. A heads up: the end of this bike trip will be an uphill climb, so be prepared to burn out your thighs!
Portland has a long love affair with roses, with their Rose Society dating back to 1889 and one of its nicknames being “The City of Roses.” This free park boasts more than 7,000 rose bushes of tons of varieties and colors in a beautiful, very Instagrammable setting. It was such a relaxing and beautiful way to start the day.
Saturday Market: Portland has some great open air markets, especially on Saturdays. There is the farmer’s market and the crafts market, to name two of the most popular. We did the crafts market where local designers and artists displayed their wears, such as handmade jewelry, clothing and paintings. It’s a great spot to pick up some unique souvenirs to bring home.
Brunch at Fireside: Make a reservation for brunch at Fireside in Portland’s Alphabet District. This small gastropub works with local farms to turn out delicious and fresh dishes. We had a lovely, leisurely lunch outside sipping on dry rose and great cocktails (get the In-Law, trust us on this.)
For brunch, I had a delicious, buttery omelette with mushrooms and gruyere cheese and my fiancé had the meat and eggs, which consisted of sausage, hash browns, toast and sunny side up eggs. We also had two cold brew iced coffees which were incredible.
The ambiance and food was impeccable, and a bonus point that it is located in an amazing part of town where we did some walking around after and found great shops and bars.
Salt & Straw: This ice cream shop is a Portland institution that has now spread to other cities on the West Coast. There are a few throughout Portland but at each you should be prepared for a long line. Having suffered through that line I can definitively say that it is worth the wait. If you go to brunch at Fireside, there is a Salt & Straw directly across the street, so save room for dessert.
There are loads of flavors to choose from, which made decision-making a bit of a struggle. In the end, we went with the sea salt with caramel ribbons which was out of this world good, and chocolate brownie, also great.
Day 3:
Cannon Beach: Dedicate a full day to Cannon Beach, just an hour and a half from Portland. We got up early and drove out to Cannon Beach for some amazing hikes with cliff views and some beach time.
Ecola Point Trail: For a scenic hike that will burn out your thighs and offer scenic cliff views of the turquoise waters at the beach, head to Ecola State Park for one of their many hikes. We did two great hikes from Ecola State Park, but there are dozens you can do based on your experience and amount of time you have.
Haystack Hill: One of the most iconic and recognizable parts of Oregon is Haystack Hill, a giant rock formation on the beach that was popularized in the 80s movie, Goonies. A beach walk alongside Haystack Hill is super peaceful and scenic and a great way to take in the views.
Schwieterts Cones & Candy: If you have been reading this blog, you know I can’t resist a good ice cream or gummy. Schwieterts is the quintessential beach-town candy shop, complete with childhood favorites such as gummy bears, nerd ropes, airheads and other favorites. They have TONS of gummies to choose from and amazing ice cream flavors. We stocked up on bags of candy for our redeye home, completely disobeying our wedding diet.
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