Portland, Oregon is a fantastic town that combines city life with outdoor living. Whether you’re a lover of arts and music, food and drinks, or nature and physical activity, Portland really has it all! Keep reading for the perfect 3-day Portland itinerary.
This site contains affiliate links to products. I may receive a commission for purchases made through these links at no extra cost to you. There are only products included that I truly love. I APPRECIATE your support!
Table of Contents
How do I get to Portland?
Portland is home to Portland International Airport, making it an easy destination for a 3-day trip. Bicycling and walking are very popular ways to get around the city of Portland, but there are also plenty of other transportation options. Portland offers the MAX Light Rail, Portland Streetcar, and TriMet bus system as ways to travel throughout the city and surrounding neighborhoods. Uber, Lyft, and other rideshare services are also plentiful in the city, making it very easy to find transportation.
Hint! Use the DiscoverCars Search Engine to find the best deal on rental cars in Portland!
What is the best time to visit?
Summer is the best time to visit Portland if you want warm, sunny weather. November through January tends to be the rainy season in Portland, so avoid visiting in winter if possible. Visiting over the summer will also allow you to enjoy some of Portland’s iconic annual festivals, such as the Waterfront Blues Festival and the Oregon Brewers Festival.
Where should I stay in Portland?
Booking.comThere are a number of distinct neighborhoods within Portland that each has its own unique offerings and styles. Downtown Portland is a great place to stay because you’ll be near a lot of public transportation, and the area is very walkable. The Society Hotel offers comfortable accommodations in a historic setting, while The Duniway Portland is a refined hotel in the heart of downtown.
Another great area to consider staying in is the neighborhood of Buckman, located just across the river from downtown. Buckman is a bit trendier with lots of laidback shops and cafes, as well as some great activities along the Willamette River that divides the city. Hotels in Buckman include the Hotel Grand Stark, a stylish and chic hotel, and Lolo Pass which offers dorm-style and private rooms for a great price.
Full Disclosure!! This site does use ads. I use the money I earn from them to keep creating these free travel itineraries for you to use! My hope is that these weekend getaways and travel itineraries make your life easier AND inspire you to get out and see the world using your limited PTO.
If you would like to downloadable PDF (with no ads) AND a day-by-day interactive map of this trip, you can purchase that download here for just 5 dollars!
Sample 3-Day Portland Itinerary
Day 1 in Portland
Morning
Start your morning off the right way by grabbing breakfast at Voodoo Doughnuts. Voodoo Doughnuts is an iconic Portland establishment, known for their deliciously quirky flavors. There are two locations in Portland and both are open 24 hours. Be prepared to wait in line to try the sweet treats as Voodoo is a popular spot for locals and tourists alike!
Afternoon
It’s time to work off some of that sugar with a stroll through the Portland Japanese Garden. The gardens are considered some of the best Japanese Gardens in the world outside of Japan itself, so take your time enjoying the beautiful landscaping. The gardens are open from 10 am-3:30 pm (closed Tuesdays) and ticket prices range from $13.50 for kids 6-17 up to $18.95 for adults under 64.
After your relaxing mid-morning stroll, head to the iconic Multnomah Falls for some hiking and amazing views. (Tip! You will need timed reservation tickets if visiting June-September). These epic falls are located just 30 miles outside of the city.
Evening
Portland is well-known as a hub for food trucks, with numerous food truck “pods” located throughout the city. You can find virtually any kind of cuisine at one of the countless food trucks located in Portland, ensuring everyone in your group will be happy with their dinner options. Pods can be found downtown, on the grounds of Portland State University, and there’s even one located in a former mental asylum.
After your food truck stop, burn off some calories with a self-guided Portland Ghost Tour. With the help of the Let’s Roam app, you will visit some of Portland’s spookiest sites!
Day 2 in Portland:
Morning:
Begin day 2 of your trip with a visit to Powell’s City of Books, the largest used and new bookstore in the world! Powell’s is simply massive, occupying a full city block, and is home to hundreds of thousands of books. Even if you’re not a big reader, it’s worth a visit just to see the sheer size of the store which is divided into nine unique rooms. Powell’s Books also features a rare book room that is open for limited hours on the weekends.
Afternoon:
Portland is home to a lot of impressive street art and murals, so spend the afternoon using one of Portland Street Art’s free maps to explore some of the best art in the city. Portland Street Art offers a walking, bicycling, and “highlights” map depending on what kind of experience you’re looking for. The best part is, enjoying all of this amazing artwork is completely free and a great way to explore different areas of the city you may not visit otherwise!
Evening:
Go out on the town by enjoying some live music, a comedy show, or bar-hopping between the plentiful breweries and themed bars Portland has to offer. McMenamins Crystal Ballroom is an amazing venue for live music, set in a historic building, and Helium Comedy Club is one of the best spots to catch a comedy show in the city. Portland is also a well-known city for producing beer, and there are a ton of breweries to explore. If you’re feeling overwhelmed with options, book a brewery tour to hit some of the best that the city has to offer.
Day 3 in Portland:
Morning
To enjoy views of the Willamette River, take a walk through Governor Tom McCall’s Waterfront Park. The park is almost 31 acres and offers great opportunities to walk or jog along the river. You’ll get great views of Portland and if you visit in spring, you’ll be able to enjoy some beautiful cherry blossoms in the Japanese American Historical Plaza, located towards the park’s north end.
Afternoon
The Mississippi neighborhood of Portland is home to lots of shops and restaurants, making it a great destination for the afternoon. The neighborhood has a lot of history and is a great place to shop local businesses and enjoy a variety of delicious foods. Mississippi is considered one of the quirkier, or more “hippie” neighborhoods in Portland, so you’re sure to be entertained as you stroll around.
Evening
To close out your trip to Portland, catch a movie at the historic Hollywood Theatre. The theater has been in operation for almost 100 years and plays new releases, classics, and quirky B-movies. The building is listed on the National Register of Historic Places and truly encapsulates the unique spirit of Portland.
Make it a road trip! Check out One Weekend in Seattle! (just 3 hours away!)
Other Things to do in Portland:
- Dinner Cruise- Enjoy a delicious dinner, sights of the city, live entertainment onboard.
- Go thrift-shopping at one of Portland’s many vintage stores
- Visit Mill Ends Park, aka the smallest park in the world
Other tips to know before visiting Portland
Always bring a rain jacket and be prepared for some rain – this is the Pacific Northwest after all! Also, Oregon is one of only two states in the U.S. (the other being New Jersey) where it’s actually illegal to pump your own gas, so don’t be surprised when an attendant comes over to help you.
One Weekend in Portland Packing List
Even though you are only in Portland for one weekend, it is best to arrive prepared to avoid having to waste time by running to the store for forgotten items. Below you will find everything (okay…maybe not everything) you will need for 3 days in Portland!
- Comfy walking shoes (for your walking tours and explorign the city). I wear my keens EVERYWHERE. Not only are they great hiking shoes, they are great for keeping your feet cool if visiting during the summer months. No socks needed 🙂
- Travel sized toiletries (shampoo, conditioner, lotion, face wash, deoderant…you know all your daily essentials). This is a perfect travel case that meets TSA regulations!
- All the clothes (this one is going to be a personal choice as to how much to bring). I am typically good with three nice dinner outfits, my favorite joggers, a comfy shirt, some atheltic shorts, and a rain jacket.
- Makeup and hair supplies
- ID and any other travel documents or itineraries needed.
- Phone charger
- Kindle or current reading book
- Any needed medications
- Airplane snacks and water bottle (bring an empty bottle along to save plastic and money at the airport and on your daily adventures)
- Sunglasses! (I always forget this one)
- Andddd of course your camera! A gopro would be fun for these adventures!
3-day Portland Itinerary Recap:
- Day 1: Voodoo Doughnuts, Portland Japanese Gardens, Multunmah Falls, Food Truck Pods, Ghost Tour
- Day 2: Powell’s City of Books, Mural Tour, Brewery tour (or comedy show).
- Day 3: Tom McCall’s Waterfront Park, Mississippi Neighborhood, Hollywood Theater.
One Weekend In Portland Isn’t Enough
As you can see, there’s SO much to do in Portland that one weekend would never be enough to see it all. You can customize your 3-day Portland itinerary based on what interests you. No matter what you’re looking for, you’ll find plenty of entertaining activities to create your own fun-filled, jam-packed adventure weekend in Portland! Andddd if you are lucky, you will be able to extend your time!
What else would you add to this “One Weekend in Portland” Itinerary?
Tip! Make sure to follow me on Instagram for more USA weekend getaways and dog-friendly adventures!
Want to take this Itinerary with you? Click below for a complete itinerary and interactive map to use during your Weekend Getaway!
Recent Posts
Austin, Texas is quickly becoming the number one destination for those looking to plan an unforgettable bachelorette party. With such an expansive area to cover, it can be challenging trying to...
Celebrating Mom's special day calls for a gift that goes beyond the ordinary—a gift that creates lasting memories and cherished moments. From indulgent spa days to thrilling adventures,...