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Itinerary for a Weekend in Portland, Oregon

Updated on July 26, 2013

If you’ve got just a few days to spend in the Rose City, make the best of them. To get the real feel for this beautiful, eclectic, west coast town, you’re better off coming for a leisurely week, but all the big sites can be jammed into a two day trip.

Day 1: Downtown and Northwest Portland

Start out in the Northwest neighborhood which is known for posh shops and upscale treats. Breakfast can be found in many gourmet restaurants or hop into one of Portland’s independent coffee shops for fresh grounds and pastries.

After filling up on Portland’s breakfast beverage of choice (only because beer isn’t normally served for breakfast), head out on your feet. Throughout the northwest in the neighborhood termed “23rd” or “Nob Hill,” you’ll find small boutiques and endless people watching.

When you’ve had your leisurely morning stroll drive or take a long walk to Portland’s world famous Rose Gardens. The International Rose Test Garden is one of a kind and give’s Portland the name The Rose City. From April through October you can wander through luscious leaves and bulbs to your heart’s content, but the best time to see them in full bloom is June. If your visit isn’t during prime time for Portland’s roses, a visit to the nearby Hoyt Arboretum and the World Forestry Museum can provide a year-round taste of the city’s natural side.

After heading back down the hill, find your way to Burnside, Portland’s most famous street and the namesake for Montgomery Burns of the Matt Groening’s (a famous Portlander) long-running cartoon The Simpsons, like many of Portland’s other streets. Mid-way down Burnside, amid a plethora of other sights you’ll find Portland’s iconic City of Books. Powell’s City of Books is the largest independently run bookstore in the nation and when you step inside you’ll find just why it’s called a city. Though you might want to take a map, which are provided by the store, you’ll thoroughly enjoy getting lost in Powell’s.

If your stomach is starting to grumble, stumble your way out of Powell’s and head north to the Pearl District where you can find dozens of delicious gourmet restaurants to soothe your stomach and tantalize your taste buds. If you’re up for a double whammy, choose to dine at one of Portland’s 31 microbreweries (more than any other city in the world!) and wash your lunch down with some hoppy goodness. Bridgeport, Deschutes, Rogue, and MacTarnahan’s breweries are a few of the big names who serve beer and food in the northwest part of town.

Walk those calories off by heading east through Old Town/China Town, toward the Willamette River. When you arrive at Portland’s Waterfront Park you’ll be greeted by eight unique bridges stretching over the wide river. Take a timeout here to watch the boats and people pass by, or keep your feet moving by heading over the double-decker Steel Bridge toward the east bank esplanade, a floating walkway edging the Willamette for over a mile. You can head back to the east side over the Hawthorne Bridge, the oldest operating lift bridge in the country, but watch out for bicyclists buzzing by.

Before heading back up town, make your way to Pioneer Square, the heart of the city, where you’ll find shopping and people watching and even the occasional event on the red brick square. When it’s dinner time, head towards Old Town in Northwest where you’ll find your choice of eateries or a little bar-hopping paradise, but before you call it a night, swing by the Shanghai Tunnel Bar to learn a little about the infamous Shanghai Tunnels running beneath the city streets. If you plan ahead, day and night tours can be arranged to take you into the spooky tunnels.

Grab your midnight snack at weird and world-famous Voodoo Donuts, where you can choose from a selection of donuts topped with everything from Fruit Loops to maple bars with strips of bacon.

Voodoo Doughnut
Voodoo Doughnut | Source

Day 2: East Portland and the West Hills

You saw the west side, now it’s time to see the part of Portland that moves a little slower, and much more to its own swanky beat. Portland’s eastside is known for its collection of walkable neighborhoods, each unique its own way. Start your day off on the east side of town for brunch in one of Portland’s excellent eateries. Screen Door, Simpatica, Mother’s Bistro, and Broder Café are a few favorites, but if you’re up for the drive, Tasty n’ Sons in North Portland was voted Portland’s best brunch in 2012 and will be well worth the drive.

When you finally roll out of your breakfast booth, spend some time wandering in any of the quaint neighborhoods where you’ll find street performers, stylish and vintage shops, and strange sights all co-existing happily. A few of the more popular neighborhoods, known mostly by the name of a main street are Hawthorne, Belmont, and Alberta.

At some point you’ll have to stop for a snack or lunch at a Portland food cart. This trend sweeping the country has become something of a phenomenon in P-town so you’ll find food carts scattered throughout the city numbering in the hundreds. Find a food cart pod, a group of food carts together, to make sure everyone gets something they like and to enjoy the seating that is typically provided by the carts in the form of picnic tables.

Before heading back to the west side, grab a cup of jo at Stumptown Coffee Roasters, Portland’s famous coffee chain and then head south a bit more to the lovely neighborhood of Sellwood. Set aside from the rest of Portland, Sellwood is like a satellite neighborhood that dances to its own tune. You might stop in a few of the vintage shops, grab a beer at one of the bars, or just drive through the neighborhood before heading over the two-lane Sellwood Bridge to southwest Portland.

Head to the hills, but first stop by the south waterfront area to hitch a ride on Portland’s aerial tram. The tram, operated by the Oregon Health and Sciences University to shuttle people up to their hilltop campus, is also a great way to get a view of Portland from above. When you’re climbing up the hill, you’ll finally get see just why this city is called Bridgetown as you take in the sprawling steel and cement structures stretching over the Willamette. From the tram you’ll be able to see a handful of tall buildings in downtown and the new structures popping up near the south waterfront, but you’ll also get up high enough to finally catch a breathtaking a glimpse of Mt. Hood, the snow-covered peak just an hour from Portland.

If you still have time and energy, check out some of the sights listed below, or else choose your favorite new part of town and grab some supper before calling it a night.

OHSU Aerial Tram and Willamette River in background.
OHSU Aerial Tram and Willamette River in background. | Source

Extra Time

If you have a little more time in Portland or are interested in some of the more traditional sights here are a few favorites.

Pittock Mansion: Once the home of a pioneer and owner of The Oregonian newspaper, Henry Pittock, this turn of the century mansion has been converted into a museum boasting a gorgeous view of the city skyline from above town.

The Chinese Gardens: In Northwest Portland you might stumble upon the Chinese Gardens, an authentic replica of a traditional Chinese garden, nestled in the middle of the big city.

Hoyt Arboretum & World Forestry Museum: Up above the city, behind the west hills, is Hoyt Arboretum an outdoor museum of trees that will give your feet a workout while teaching you a few things about the northwest’s giants. The nearby Forestry Museum offers a wealth of knowledge and beautiful sights.

Portland Art Museum: This oldest art museum in the Pacific Northwest has over 40,000 artworks and plays host to various touring exhibits.

OMSI: The Oregon Museum of Science and Industry, along the east bank waterfront, is full of sights and activities that are fun for kids and adults alike.

Zoo & Children’s Museum: The kids will love Portland’s Public Zoo and adjacent Children’s Museum.

Multnomah Falls: Well outside the city limits but just a short 30-45 minute drive from downtown is the towering Multnomah Falls, a beautiful waterfall and invigorating hike that will be well worth the drive. On your way out don’t nap or you’ll miss the breathtaking views of the Multnomah Gorge towering over either side of the river.

Lan Su Chinese Garden
Lan Su Chinese Garden | Source

Seasonal Faves

These places might not be open year-round, but they draw crowds of locals and tourists alike.

Portland Farmer’s Market: Running along the southwest side of the Willamette River, the Farmer’s Market (which runs on Saturday’s and Sunday’s throughout the summer and fall months) bustles with businesses pushing kitschy crafts, eclectic art, and, of course, lots of yummy treats.

First Thursday in Northwest: This monthly event is a favorite for art buffs as the doors of the Pearl Districts art galleries fly open welcoming the public in for free visits, camaraderie, and often libations.

Last Thursday in Northeast: Quite different from its northwest counterpart, this celebration of art spills out onto the streets as the Alberta neighborhood overflows with artists, performers, and food carts. The event is such a sight that crowds passing through almost resemble a parade as hundreds pass down the closed-street, slowly taking in the sights.

Summer Street Fairs: Many of Portland’s neighborhoods host their own unique street fairs throughout the late summer offering handmade crafts, music, art, and food to residents and tourists.

South end of Portland's Saturday Market on the Willamette River.
South end of Portland's Saturday Market on the Willamette River. | Source

Finding Portland, a time lapse video from Uncage the Soul Productions made for TEDx.


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