As I look to refresh and renew some of my older content, I knew that I wanted to transform my travels to Portland into a guide for people to create their best weekend in Portland. We had such an amazingly fun time when we visited the city. This guide to Portland will provide you with plenty of adventure to choose from. No matter what you’re looking to do in the city, or its surrounding countryside, you’ll be able to plan your best weekend in Portland after reading this guide.
While a lot of it is based on my trip, I’ve also included places I wish we would have visited and locations I didn’t even know about back then! Once you finish reading my guide to Portland, let me know how you plan on creating the best weekend in Portland in the comments!
Fabulous Food for the Best Weekend in Portland
Portland is a city packed with excellent food choices. Our trip featured a couple iconic places to eat during our weekend in Portland. Each of these were fantastic, but largely limited to the neighborhood we stayed in. So not only will you get my personal insight on my favorites, but also some places I wish we would have tried!
During our weekend in Portland, we had a couple of amazing meals along in the Alberta Street Arts district. The first of those happened to be one of the best grilled cheese sandwiches I’ve ever had. Back then the Grilled Cheese Grill was located inside a bus, but now they have a more permanent location inside of The Knock Back bar right on Alberta Street. We also really enjoyed the Radio Room, which features a heated rooftop patio!
Once you’re downtown, there is a wealth of dining options available. After visiting Powell’s City of Books (and spending a few HOURS there), we had to grab a slice of pizza from Sizzle Pie. I’m a big fan of pizza and this was definitely a couple of delicious slices. Plus, they have vegan options! One of the more unique aspects of the restaurant scene in Downtown Portland is the huge number of food trucks and carts. You can find them all across the city, usually near or in public parking lots. As we wandered downtown during our weekend in Portland, we stopped at Frida’s Kitchen and it was delicious!
There were definitely a couple of places I wish we had gotten a chance to eat at on our trip. One of those is the famous Screen Door. Being from the south, I always enjoy a good southern meal and Screen Door serves a mighty fine assortment of southern cooking. It’s honestly hard to go wrong with starting the day off with some delicious chicken and waffles, or even a heaping helping of biscuits and gravy. The other option recommend to me by friends that we missed was DarSalam. It’s an Iraqi/Middle Eastern cuisine, which is highly rated and one of their favorite stops when they’re craving something different.
Spend Some Time in The Great Outdoors
For a major city, Portland has a surprising number of ways to spend time outside. To me, some of the best weekend activities in Portland don’t have a roof. There are options for pretty much everyone and you can access a lot of these without needing a car!
You can start your weekend in Portland at one of the great parks in the city. Forest Park is one of the best urban “wilderness” parks in America. This well preserved space spans over 5,200 acres and features over 80 miles of rugged trails for use. That includes one of the few National Recreation Trails located in a major US city, the 30 mile Wildwood Trail. There are many different access points across the park, though the amount of parking available varies quite a bit. However, Portland’s wonderful public transportation network is connected to most of the more popular trail heads. For more information on Forest Park and all it offers, check out it’s official city website.
Outdoor weekend activities in Portland extend way beyond the city limits. The Columbia River valley is chock full of awesome hikes. I’d suggest starting your exploration of the valley with a visit to Multnomah Falls. Easily accessible by car or bus, the view of the falls from the bottom is amazing. However, you can also venture much closer to falls by hiking up to the iconic Benson Bridge. The truly adventurous could even tackle the challenging hike on the Larch Mountain Trail. There is so much to do in the Columbia River Gorge, you could practically spend a whole weekend just there!
For those who prefer guided tours of the great outdoors, then you’re in luck as well. It’s quite easy to book a guided tour that can help you maximize your fun during a weekend in Portland. For a full day of hiking, scenic views, and wineries then check out this Columbia Gorge Hike, Wine, and Discover tour by Terran Travels. If you’ve only got a few hours to spend, then I’d recommend a Gorge Waterfalls Tour hosted by Wildwood Adventures.
Museums and Other Cultural Offerings in Portland
Museums are often the centerpiece of what many tourists plan their city vacations around. I absolutely love a good museum, especially when they are connected to the city they’re in. They are also an awesome way to explore the culture of the city you’re in. That’s the whole point of heading to an awesome city like Portland!
One of the #1 museums to see while enjoying the best weekend in Portland is the Portland Art Museum. It is the oldest art museum on the West Coast and boasts an impressive array of art from around the world. Among the highlights of the Portland Art Museum is the extensive collection of art from Japan, China, and Korea. This includes more than 800 Japanese wood block prints. As of 2023, the Portland Art Museum is undergoing an extensive renovation. However, they have a series of rotating exhibits still available to view which definitely makes it worth stopping by during your weekend in Portland.
Portland also features another fantastic way to explore Japanese culture by visiting the Portland Japanese Garden. On my trip to Portland, this was one of my favorite experiences. These gardens are designed to fill their visitors with a sense of serenity or peace. Even on the busiest weekend in Portland, it’s good to find time to relax. It is a vacation after all! The Portland Japanese Garden is also a place where you can immerse yourself in other parts of Japanese culture. For me, it was a must visit place and honestly no guide to Portland is complete if it doesn’t recommend a stop here.
If you want to get your culture in smaller does across the city, then consider exploring the amazing street art around Portland. The city is full of street art and you could make a full day of it. In fact, if that’s how you want to spend one of your days creating the best weekend in Portland, then following this guide to Portland Street Art!
Neighborhoods to Stay in for the Weekend
There are two schools of thought when picking what part of town to stay in. The first is getting as central as possible, helping to minimize distances you might have to go to see all the sights. The second is choosing a neighborhood that fits your personal vibes or is closest to the one or two places at the top of your list. I fall into group number two and Portland is a great place for trip planners like me!
Our trip centered on the eclectic Alberta Arts District. While our beloved Caravan – The Tiny House Hotel, is no longer open (a casualty of the pandemic), there are still a number of excellent places to stay in the area. The most “hotel-like” location in the Alberta Arts District is the Kennedy School just a few blocks from Alberta Street. It’s part of a collection of hotels owned by local company McMenamins. If you’re seeking to rent a whole home to create the best weekend in Portland, consider this awesome spot right on Alberta Street.
If you’re wanting to create the best weekend in Portland by staying closer to downtown, then you’ve got plenty of options available. My first suggestion would be McMenamin’s Crystal Hotel. It’s located right on Burnside, just a short walk from the world famous Powell’s City of Books and a delicious slice of pizza at Sizzle Pie. The best hotel with views of the Willamette River would be the Kimpton RiverPlace. Part of the IHG family of hotels, it offers a high-class experience for with which to create your best weekend in Portland.
Finally, I’d be remiss if I didn’t add in a couple more “Portland” like places to stay in this guide to Portland. While the original tiny house hotel might be gone, you can still get a similar experience when visiting Portland. Tiny Digs Hotel of Tiny Houses features a number of beautiful tiny homes available to stay in. Tiny Home hotels are a really neat experience, so if you’ve never stayed in one before I suggest doing it at least once. For a more laidback experience that’s a bit out of town, checkout St. Johns Inn. Located along the Willamette River, this inn has been greeting guests for over 100 years. It’ll definitely provide you with a different experience than anywhere else in the heart of the city.
Revisiting My Weekend In Portland
It’s hard to think that my weekend in Portland was over five years ago. Part of our massive Pacific Coast trip that included our drive along the Redwood Highway, Portland was the culmination of that adventure. The end of a long road trip is exciting and at the most energy drained point of the whole adventure. The couple of days we spent in Portland were laid back and an awesome way to have wrapped up that trip.
Being honest with myself, there wasn’t anything I feel we missed out on when visiting. A weekend in Portland truly seemed like the perfect amount of time. Obviously we could have seen and experienced more, but I don’t think that was down to a lack of time. It was a choice to just enjoy the city. With all that said, there’s still ways I’d change our trip.
The biggest aspect would be visiting later in the year. We didn’t get to see the rose garden in bloom or the surrounding area in warmer weather. Having lived in Florida my whole life, late April and early May was the best time of year. That isn’t necessarily the case in the cooler climate of the Pacific Northwest. I think to absolutely maximize the chance of having the best weekend in Portland, I’d have visited closer to the end of May instead.
Another thing I’d consider changing would be making Portland the focus on my trip. While this sounds obvious, it really wasn’t part of the original plan. Portland originally was the best city to fly home from, so we decided to end the trip there. That meant I didn’t put as much effort into planning what we were going to be doing in the city. This is a similar problem I ran into with our trip down the Great River Road when we ended in New Orleans. We also were tired and drained from the long road trip up, so the city served as a cap to our adventure rather than being the adventure itself. I obviously haven’t yet learned my lesson, so hopefully you will!
Final Thoughts on Planning Your Weekend Trip to Portland
When creating the best weekend in Portland, it’s going to be all about what fits your tastes. This guide to Portland is honestly just scratching the surface of what this fabulous and funky city has to offer. However, I 110% recommend taking advantage of spending time outside while you’re in the city. There are a number of easily walkable parts of town, many of which are full of neat shops or other hidden experiences. The Pacific Northwest is known for it’s occasionally unpredictable weather, but don’t let that rain on your parade or time in the city. Portland is extremely high on my list of cities to make a return visit to so that I can have another great weekend in Portland!
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