3 Days Portland Itinerary: A Guide For An Epic Weekend in Portland

Do you like donuts? How about craft coffee? Biking? Stunning fall foliage? Walking around in the rain without an umbrella, you badass you? Welcome to Portland, Oregon – you’re gonna love it here.

My weekend in Portland was so much fun. I left feeling like I thoroughly got a crash course on the city. Grab your organic fair trade brew, in this post I’ll be sharing my 3 Days Portland Itinerary aka A Guide For An Epic Weekend in Portland.

I’ll be sharing my recommended hotels, fun hidden gems, my favorite restaurants, which donut shop is the best (this is legit a feud locals have!) and tons of handy travel tips for having the best 3 days in Portland!

3 Days Portland Itinerary: A Guide For An Epic Weekend in Portland

I flew up to Portland with a friend for a girls trip weekend! Full disclosure, we live in San Francisco and caught a very late flight from California to Portland. We landed close to 10 pm and didn’t get to our hotel until almost midnight. We wanted to wake up in Oregon to maximize our trip! If you have that option, I recommend it.

Is A 3 Days Trip to Portland Enough Time?

On that note, 3 days is totally enough time. Based on how media talks about Portland and it is a major west coast hub, I expected it to be much larger – like, the size of Seattle. In reality, Portland has more of a small-town feel where it takes 10 minutes or less to drive anywhere you want to.

Being totally honest here, by the middle of the first day, I had the downtown area memorized. Not a bad thing, but not what I expected. Good thing we planned a whole day outside of the city in the woods, or I would have gotten a little stir crazy as there is only so much food and drinks you can pack into your body in one weekend!

Cute Portland Hotels You’ll Love

Oh my gee, Portland has a ton of hotels! Leave it hipsters to make sure hotels are trendy and charming. When you are figuring out where to stay in Portland, I recommend that you stay downtown or as close to downtown as possible. This will make it easier for you to explore and most likely you’ll be able to walk for most of the trip! Save that Uber money.

• Hotel Monaco: We stayed at Hotel Monaco in downtown Portland.  This place is so freaking cute! Think fun wallpaper, bright colors, classy decor and dogs to make friends with because it’s a pet-friendly hotel. They also have a free happy hour each night in the lobby, bites included! Plus, they have bikes available for guests so you can explore the city on wheels. Score! Book best deal here. 
• The Society Hotel: Looking for a hotel with a rooftop? On a clear day when it’s not raining, I have a feeling the Society Hotel’s rooftop is popping. This hotel is more of a hostel, has a chic warehouse feel and is a cute budget option, usually ranging at about $50 a night (but you get shared bathrooms, FYI!) Book best deal here. 
• Airbnb: We love using Airbnb when traveling, especially with groups! There are SO MANY cute Portland Airbnbs, the locals really know how to rock vacation rentals. I actually rounded up my favorite Airbnbs in this post. PS use THIS link for $40 off your stay!

What To Pack For Portland (HANDY! USE THIS!)

Portland can be a challenging city to pack for. It rains a lot – but not the kind of rain you may be used to. It’s lighter here, more like a steady mist when Mother Nature really gets going. Locals also hardly ever use umbrellas and instead opt for waterproof jackets and rain boots. 

It gets hot in the summer but winters are mild – I visited Oregon in January a couple of years ago and didn’t need more than jacket (aka no heavy winter coats needed unless you’re spending a day on Mount Hood!)

Here’s the important things to pack:

• Waterproof purse to keep your phone, camera, etc dry! This one is my go-to, been using it for years. 
• Rain jacket (this is my favorite one of all time, so cute!)
• Cute waterproof boots like these
• Sweater
• Hand lotion (my hands always get dry after being wet all day!)
• Waterbottle
• External Phone Charger (I never travel without this one!)

Alright, let’s dive into my Portland weekend itinerary! Time to fall in love with the Pacific Northwest! 

Friday in Portland

If you haven’t arrived yet, check-into your hotel (again, I love Hotel Monaco!) grab a free bike rental and time to go get breakfast! We borrowed uber-cute vintage-style bikes from Hotel Monaco and opted to explore the city that way for the morning. They have about 7ish bikes and it’s first-come, first-serve, so make sure you claim one early if you want it. If you’re staying in an Airbnb, use Biketown, the Portland city bike-share program. If you plan on biking more than one day, I recommend signing up for the monthly pass for $12. 

Head over to Blue Star Donuts. There’s a few of them in Portland. If you’re staying downtown, head to the one on Washington Street. I’ve been hearing about Blue Star’s Bourbon Blueberry Basil donut for months now and I must say, the flavor lived up to the hype.

They have outstanding donuts and frostings. I also tried the passion fruit with cocoa nips and holy cow! I’ve never tasted a more flavorful donut in my entire life. Voodoo Doughnuts is that famous place you always hear about. It’s a big local feud over which has better donuts. I’m team Blue Star! 

After, we biked to the base of Washington Park, looped down through the Pearl District to the riverfront, weaved through Chinatown and Downtown back to Hotel Monaco around Noon. The city is very peaceful and there weren’t as many cars downtown as I thought there would be. It’s not the bike capital of the world, but it is really bike-friendly! You can, of course, do a walking tour instead of biking. 

We stopped for coffee at Heart coffee shop. We actually came here more than once as it’s a small coffee shop chain in Portland with the best spicy chia I’ve ever tasted. Another local favorite is Stumptown Coffee Roasters, so if you pass by one of those, know they’ll serve a great cup of coffee! 

For lunch, beeline to Tasty n Alder, a restaurant on Alder and 12th street. For some reason, at 1pm on a normal Friday afternoon, the waitlist was over an hour, so I recommend making reservations. While waiting for our table, we walked around the local shops, there are a few really cute boutique stores in this area.

At Tasty n Alder, we just grabbed food, but looked like they had a great tap menu and wonderful sides to try as well. It has a fun modern vibe with wood, concrete and cool light fixtures. It’s a fun place to hang out! 

For happy,  Portland City Bar Grill has stunning views and a great happy hour deal! It’s on like, the 30th floor of a downtown building. As someone who loves drinking on tall places, this was a favorite of mind. 

I recommend heading there closer to 4pm when happy hour starts so you can grab a seat next to a window, watch the sunset over the city and stay for the evening. They have jazzy piano music and a very classy, romantic vibe. Happy hour beers were under $5 and I got Mac n Cheese for $6. Have dinner here to go pick up something yummy from one of the many food carts in the city! 

• No Portland weekend getaway is complete without trying a food cart. It’s like a whole movement here. I have a friend who used to live in Portland and his blogged solely about all the food carts in the city. Check it out here! 

For a late night drink, go to the Whisky Library to try and sample some fabulous whiskey in a fabulous spot. It has an old-world library feel, almost makes you feel like you walked into a Scottish library. Make sure to make reservations for here, the wait can be up to 2 hours if you don’t.

We couldn’t get in that evening, so we hit up another cocktail bar, which was full of old people, then moved onto Kelly’s, a dive with motorcycles hanging from the ceiling. This was more my scene-  cheap but good beer, tasty bar food, cozy booths and people watching. We ended the night at around midnight.

Saturday in Portland

Set your alarms early, today you’ll be taking a short day trip from the city! First, breakfast. Check out Pine State Biscuits for breakfast (they have really good biscuits to fuel your day of adventure!) 

Strap on your hiking boots and go explore the outdoors around the Portland area today! Start at the Witch’s Castle, a small hike within the city of Portland. Park on the road, walk down the surrounded by green trees to find an old stone “house” hidden in the woods!

If it’s pouring rain, swap the Witch’s Castle hike for a visit to Pittock Mansion, a famous French Renaissance-style château built in 1914. It houses tons of interesting history from Portland’s early days and has a stunning garden with great views! 

After exploring the hills of Portland, get ready for one of my favorite sites in the whole state: Multnomah Falls!! A short drive from the city is this beautiful waterfall. To get there you’ll drive along the Columbia River Gorge. As you can see from all the colorful photos, we visited Portland in October and this drive was just jaw-dropping. Hello fall foliage!

Multnomah Falls is 620 feet tall and just commands attention. You can walk at the base from the safety of the trail and that classic bridge. Heads up, you’re going to get wet on that bridge because the mist is so strong! If you want you can hike 2.5 miles up to the top of the waterfall. It can get busy on the weekends and parking can be tough, but wait it out, it’s so worth it!

On our visit, we kept driving and circled around Mount Hood, but that’s optional and will take the rest of your afternoon.  If you have more than a 3-day weekend, I highly recommend spending a night in the Mount Hood Territory. We had so much fun on our return visit the next winter! 

• Looking for other day trips? Cannon Beach is about 1.5 hours from Portland and is the state’s most popular beach due to the large Haystack Rock in the ocean. If it’s a hot day out, a beach day may be more fun than a waterfall visit! 

Depending on when you get back to the city, you may be able to visit the Portland Saturday Market, an arts and crafts market. It’s the largest continuously operated outdoor market in the United States! Come for flea market items, local boutique crafts and food. 

For happy hour tonight, hop over to the East Side of the river on Burnside Street to Rontom’s, a local favorite watering hole. The inside is wide open with lounge seating, but the outside patio is the best. It’s covered and has fires going, so it was cozy-chic place to sip on drinks.

For dinner, pop over either to the pizza by the slice joint next door to Rontoms, or The Fireside. The later focus on organic, local farm foods and offer a patio to sit on during warm evenings.

Sunday in Portland

We were craving a good brunch on Sunday morning and ate at Screen Door on the East Side. There’s indoor and outdoor seating, though I recommend the outdoor for fresh air! I got the Garden Grits which were perfectly cheesy and savory. My friend had the oyster sandwich and it tasted so fresh.

Screen Door is famous for their huge fried chicken and waffles!

People around us were having fried chicken and waffles. Be warned, this dish is meant to serve two people because it’s stacked with 3 HUGE pieces of chicken on top. Everything on the menu looked so great and is a place to go for southern food in the city.

If you can still eat, while you’re on this side of the city, visit Salt and Straw! It’s so famous in Portland, so famous they opened up a few locations here in California, we have a couple in San Francisco actually. 

Opt to do an ice-cream flight and try a lot of flavors. We tried olive oil, lavender, strawberry basil and brittle flavors. My favorite was the olive oil. You wouldn’t think it would be good, but it was!! So unique and nothing I’ve ever had before. They always have seasonal flavors, so try some of the extra strange ones, too (like blood or cricket!)

Roll yourself out of the ice cream shop and drive to the famous International Rose Test Garden! there are free guided tours daily at 1:00 pm and the garden features over 10,000 rose bushes. Sadly when we visited it was closed for renovations or something so we didn’t get to visit but I want to check this out next time as I hear great things. Plus, you know how much I love flowers!!  

Next we visited the Portland Japanese Garden which we’ve heard great things about. I’m going to be honest – it was beautiful but really small and I felt slightly cheated on the $16 and the long wait to get inside. We tried taking our time walking around it and it still only took about 25 minutes to walk around the whole thing.

It was pretty in the fall with the changing leaves, but I imagine it’s drop-dead gorgeous in the spring with the trees blossoming so if you are visiting Portland in the spring, head here! It would be worth the wait to see all the flowers (cheaper than a plane ticket to Japan!)

After the gardens, it was time for us to head to the airport! That with that, we wrapped up 3 perfect days in Portland. I hope this helps you find fun things to do in Portland Oregon on your weekend trip!

Three days in Portland should leave you full, caffeinated and happy. I can’t wait to go back – it’s such a fun city and state! Got any questions? Leave a comment below or DM me on Instagram @thewhimsysoul and I’ll be happy to help!

Love Oregon? Here’s Some Other Travel Guides You May Like

1. Painted Hills (Looks like Mars!)
2. Umpqua Hot Springs Guide
3. Fun Things To Do in Mount Hood
4. Winter in Oregon Itinerary (From the Mountains to Bandon on the Coast!)
5. Our California to Oregon road trip route