How to Have a Fun 3-Day Weekend in Portland

portland oregon sign

Portland had been on my bucket list for quite some time. With good food, coffee, books, the beautiful outdoors, and friendly people, what more could you want from a city?

My cousins and I enjoyed a fun and rejuvenating weekend in Portland recently and I’m sharing our three-day itinerary so that you too can get in on all this city has to offer.

Day 1:

portland blue star donuts
Blue Star Donuts

Start the morning off right with coffee and donuts!  Heart Coffee has one of three locations in the West End neighborhood near the Pearl District. They are known as one of the best places in Portland for a quality cup of joe.

Just a block away from Heart Coffee, you’ll find gourmet donuts at Blue Star Donuts. With flavors like Chocolate Almond Ganache, Lemon Poppy, and Maple Bacon, you really can’t go wrong with any flavor at this much loved spot.

portland powell's books

Also in the West End neighborhood is Powell’s Books. If you’re a bibliophile like me, make this a must-visit spot when in Portland. Powell’s is an institution and famous for being the world’s largest independent bookstore so it won’t be hard to find a good read or two no matter your literary taste.

portland saturday market

After browsing the shops in the West End and Pearl District, take a 10-15 minute walk to the Old Town for the outdoor Portland Saturday Market. Open on Saturdays and Sundays, local vendors sell handmade arts, crafts, and food. It’s a great place to grab lunch, listen to live music, shop, and people watch.

For dinner, I highly recommend Screen Door for an amazing menu of Southern/Cajun/Creole dishes. Make sure you get there with an empty stomach and before it opens at 5:30pm because there will be a line.

Day 2:

portland pine state biscuit
The Reggie at Pine State Biscuit

With a full day of sight-seeing ahead of you, you’ll need to start the day off right. Go to Pine State Biscuits for a hearty breakfast. The Reggie with an Egg comes with fried chicken, bacon, cheese, and gravy and is topped with an egg. This plate will definitely last you until lunch time.

portland japanese garden
Portland Japanese Garden

There are lots of lovely things to do in and around Washington Park starting with the Portland Japanese Garden. Get your zen on and take a stroll among the elevated plush gardens and ponds. I suggest going early as it gets crowded by noon.

portland rose garden
International Rose Test Garden

Down the road from the Portland Japanese Garden is the International Rose Test Garden where you can literally stop and smell the roses! Unlike the Japanese Garden, this garden is free to admire the thousands of rose plants that are in bloom between May and September.

portland pittock mansion
Pittock Mansion

Take a short car ride to Pittock Mansion for a slice of Portland History. Located on the West Hills of Portland with gorgeous views of the city, the former mansion-turned-museum is over a 100 years old and was owned by the famous Pittock family who were very active in advancing many industries within Portland.

portland pip's donuts

For an afternoon pick-me-up, you must go to Pip’s Original Doughuts which was my favorite donut shop in Portland. They serve mini-donuts in flavors such as nutella and sea salt and cinnamon and sugar and you can also order a chai flight to sample five different chai blends to go with your donuts.

portland mt. tabor park
Mt. Tabor Park

Mt. Tabor Park is just one of many places where you can enjoy the beautiful outdoors in Portland. The park is actually a volcanic cinder cone with lots of hiking trails, playgrounds, and reservoirs. Get your exercise in and then rest on one of the rolling hills to enjoy the fall foliage and scenery around you.

For dinner, go to Cheese and Crack Snack Shop for amazing cheese and charcuterie boards and wine for pre-dinner appetizers and then Pok Pok on SE Division Street for tasty Thai cuisine.

Day 3:

portland voodoo doughnuts

Ok, last donut stop I promise. You can’t really leave Portland without trying the famous and kitschy Voodoo Doughnut. TThere will most definitely be a line so do what my cousins and I did and grab a coffee at Stumptown before going to Voodoo early in the a.m. when there will be no line. Enjoy your early sugar rush!

For a more filling breakfast, you will love Tasty n’Alder which serves delicious family style plates  including cast iron frittatas, potatoes bravas, french toast and cheese boards. On the weekends, the wait is long so save this place for a weekday morning to avoid the crowds.

portland aerial tram
View of Portland from the Aerial Tram

To really see all of Portland, take a ride on the Aerial Tram. A round trip fare is less than $5 for a 4-minute ride each way and on a clear day, it’s a prime opportunity for great photos. Try and avoid the rush hour when it will most likely be crowded and opt for the middle of the day for the ride.

portland tilkum crossing
Tilkum Crossing

A short walk from the Aerial Tram is Tilkum Crossing, or the Bridge of the People which goes across Willamette River in Portland. The bridge opened not too long ago in 2015 and has great pedestrian and bike paths on either side of the bridge for a good walk that’s peaceful and has great views of the Portland skyline.

portland salt and straw
Salt and Straw

After your walk, ride over to NW 23rd Street for a neighborhood full of restaurants and shops including Portland original Salt and Straw. This popular ice cream chain serves flavors like sea salt with caramel ribbons, cinnamon snickerdoodle, or honey lavender. This treat will definitely fill you up and could serve as your lunch before it’s time to head to the airport.

Need even more recommendations?

Visit Multnomah Falls or the Tillamook Factory or one of the many breweries in town. If you’re still hungry, Jake’s Grill and St. Honore Bakery are a couple more places for a good bite to eat.

My cousins and I stayed at the historic Benson Hotel in downtown Portland and we loved it! It was within walking distance to the Pearl District and a car rental service. We used a combination of a car rental, Lyft rides, and walking and it worked out great for us!

Do you have any tips for things to do and eat in Portland? Leave a comment below!

Leave a Reply