Portland Itineraries

Exploring Southeast Portland

Family Friendly Portland Fun

Hanging Out in Portland’s Living Room

Northwest Portland: Stroll, shop, dine, hike

Portland Travel Hacks

Portland’s Best in 24 Hours

Portland’s Lodging: Boutique, Fun, Funky, Fancy

Slacker’s Charm in Portland’s Old Town/ Chinatown

Feasting and fun in the Rose City

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Portland rewards those who wait for clear skies. During the cool, cloudy, damp winter and early spring, most locals carry on without an umbrella — almost as a badge of honor. But once the sun emerges, few cities match the Rose City’s beauty.

Located between snow-capped Mount Hood and the unspoiled Oregon Coast (both less than a two-hour’s drive), Portland is a decidedly outdoorsy city with acres of forested parks, riverfront gatherings, renowned restaurants and pubs, and clusters of eclectic shops tended by fun, quirky people.

The city takes immense pride in its glorious rose gardens and greenways, and many of its residents wear the term, “tree-hugging, bike-riding hipster” with pride. What’s quirky about it? Well, the state has no sales tax, recreational marijuana was just legalized and residents aren’t allowed to pump their own gas.

And folks seem to like it that way.

It’s a city that brews its own craft beer, roasts its own hearty coffee and features some of the finest culinary establishments in the nation. In fact, this past year, the Washington Post anointed Portland as the top food city in the nation. The city also has an amazing selection of food cart pods for more casual fare.

Portland Neighborhoods

The Southwest incorporates most of downtown Portland. It’s where the office building jobs are during the day, and where folks go for fine dining, a show or museums at night. It’s bordered on the east by the Willamette River and Waterfront Park, where people bike ride, and enjoy music and food festivals. To the west, you’ll find the Rose Test Garden, zoo and the suburbs of Beaverton and Tigard. Keep going two hours and you’ll arrive at the glorious Oregon Coast.

This is where Portlandia comes to life. It has the hippest people, coffee houses, dining and shops. The neighborhood’s popularity has transformed it into one of the more expensive places to live. The dining along Division and Clinton is a magnet for the entire city. If you keep heading east along Powell Blvd., you’ll drive right up to Timberline Lodge on Mount Hood.

North and Northeast
This is where working-class neighborhoods and gentrification collide. It’s more economically and ethnically diverse than other parts of the city. The Alberta District is known for its street festivals and the Mississippi neighborhood is evolving from an industrial area to being dotted with lofts and condos. As with most of Portland, it has its share of incredible dining venues. If you keep going north, you’ll join the traffic jam on I-5 over the Interstate Bridge into Vancouver.

Portland’s most upscale residential neighborhood also has the best selection of boutique shopping, wonderful restaurants, and the largest urban green space in Forest Park. Finding parking is a continual trial as people circle looking for a miracle. In the neighboring Pearl District there is a fine collection of boutiques, classic brewpubs and nightclubs. If you head out of town along Highway 30, you’ll drive through timber towns and arrive in Astoria.

Old Town/Chinatown
This historic section of Stumptown presents a mix of exciting nightlife, colorful markets, captivating dining and, unfortunately, a large number of homeless folks. People enjoy the late-night bar scene, going to the Saturday Market and the gorgeous, serene Lan Su Chinese Garden.

First time here? Start with a riverfront stroll

To become acquainted with the Rose City, walk along Tom McCall Waterfront Park: a wide, 1.5-mile scenic stretch of lawn that serves as the city’s gathering place. On most days, the walk is perfect for bike riding, jogging or strolling along the Willamette River.

At the northern end of the park on the weekends, visitors will find Saturday Market, a tie-dyed throwback of artisan craft booths and food carts. Started in 1974 as a Bohemian bright idea, Saturday Market is America’s largest, continually operating arts and craft market — attracting more than a million visitors each year.

To get the best view of the city, walk across the Steel Bridge walkway to the east side. Continue onto the Vera Katz Eastbank Esplanade, a floating, 1.5-mile walkway offering a panoramic view of Portland’s downtown skyline. At the southern end of the walkway, you can rent kayaks and go for a peaceful paddle.

For more about recreational marijuana, see ‘Background’ in the yellow bar above.

Dive Into These Portland Itineraries

Discover Iconic and Stylish Northeast Portland … Street festivals, pub crawls, stylish shopping – and golf
Exploring Southeast Portland … Where the Portland in your mind comes alive
Family-Friendly Portland Fun … Hiking, paddling, pedaling and rainy day options too
Hanging Out in Portland’s Living Room … Where Portlanders get together
Northwest Portland: Stroll, shop, dine, hike … Nature, shopping and sophistication
Portland Travel Hacks … Create a stress-free, fun-filled Rose City vacation
Portland’s Best in 24 Hours …Short on time? No problem with these highlights
Portland’s Fun, Funky and Fancy Lodging … Don’t stay in a cookie-cutter hotel room
Slacker’s Charm in Portland’s Old Town/Chinatown … Take a walk on the wild side

When To Go

Because of its mild climate, people visit Portland year-round. So when to come depends upon:

a) your tolerance for rain; and
b) what activities you want to enjoy.

Portland is green for a reason. It averages 39 inches of rain a year, most of it falling between October and May. The city itself doesn’t get a lot of snow (the average low temperature in January is 36° F) but nearby Mt. Hood does, attracting hordes of snowboarders, and downhill and cross-country skiers. So winter sports enthusiasts, will not only find outstanding facilities on the mountain, they can indulge in Portland’s famous dining and brewing scene.

In June, the city kicks off the summer with a wealth of festivals and river activities. The blueberries are ripe, the roses in full bloom and there always seems to be a party along the waterfront, or a farmers market in a neighborhood park. Hikers head out to the Columbia River Gorge or into Forest Park, while water lovers row their Dragon Boats or take a Sternwheeler Tour. The temperature scoots up into the 80s in July and August, before settling back down to a glorious, crisp autumn, just in time for football season.

Events and Holidays

Here’s a list of some of the top festivals and events in Portland. For an even more detailed listing of upcoming events, go to Travel Portland’s events calendar.

Oregon Truffle Festival

Chinese New Year Cultural Fair
Portland Seafood and Wine Festival
Chamber Music Northwest Winter Festival
Portland Winter Light Festival
Portland International Film Festival


Kells St. Patrick’s Irish Festival
Spring Beer & Wine Fest

Portland Cinco de Mayo


Rose Festival Starlight Parade
Rose Festival Dragon Boat Races
Rose Festival Grand Floral Parade
Portland Pride Festival
Festival of Balloons

Waterfront Blues Festival
Portland Craft Beer Festival
Oregon Berry Festival
Portland Highland Games


Columbia Slough Regatta

Feast Portland

Portland Greek Festival

Wordstock: Portland’s Book Festival
NW Filmmakers’ Festival


Festival of Trees

What To Pack and Wear

Pack casual clothes. Portland is casual, almost to a fault. Even downtown, it’s not unusual to see locals wearing sandals and shorts in nice restaurants. So unless you also have a business meeting, you can leave your slacks, dress shoes, suits and accessories at home. You’re on vacation. One of the benefits is that here, you can dress in whatever you’re most comfortable wearing. Also, make sure you pack casual, comfortable shoes for walking and hiking. You don’t have to go on a rigorous trek unless you want to, but there are plenty of comfortable walks, from Waterfront Park and Forest Park to nearby Multnomah Falls. Also, unless you’re visiting in the summer months, do pack a jacket for the rain and a sweater for the chill.

What it Costs

Abstract Pricing at a Glance

Prices often fluctuate dynamically depending on capacity, seasonality and deals. We don’t want to lead you astray by quoting exact prices that quickly become wrong. To give you a rough idea for budgetary planning purposes, though, we have indicated general price ranges for all points of interest.

Price ranges are quoted in $US.

See & Do
N/A => Not applicable
$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$$ => Tickets $26 per person

$ => Rooms less than $100 for a double
$$ => Rooms $200 for a double
$$$ => Rooms $300 for a double

$ => $1-15 per person for a meal (without alcohol, tax, tip)
$ => $16-40 per person for a meal (without alcohol, tax, tip)
$$$ => $41 per person for a meal (without alcohol, tax, tip)

N/A => Not applicable

$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$ => Tickets $26 per person


You don’t need a car to get around the city — providing you’re IN the city. Otherwise, getting out to the burbs and other areas, you’ll encounter traditional, commuting traffic jams just like anywhere else. The city’s clean, efficient MAX Light Rail is just the ticket to get about town. It speeds to the airportzooTimbers MLS and Trailblazers NBA games and shopping malls. There is also a Portland Streetcar, which runs on an eight-mile continuous loop, providing access to many of the city’s trendy neighborhoods and to the Aerial Tram, a popular tourist stop for those who want a bird’s-eye view of the city.

However, many opt for two-wheeled transportation. In the mid-1990s, the city built a bike network with bike lanes, improved bridge access, bike corrals and 30 miles of bike boulevards that wind through Portland’s neighborhoods. In 2015, Portland opened Tilikum Crossing, the nation’s first multimodal bridge to carry streetcars, light rail, buses, cyclists, and pedestrians — but no private cars.

Bike rentals are easy to come by, and today there are restaurants, mass transit and hotels that cater to cyclists. And it even celebrates its two-wheeled love affair with bike festivals in June. Here, you’ll find every type of rider, from those who preen in colorful, clashing gear like modern-day Lance Armstrongs, to cyclists riding without a stitch for the annual Naked Bike Ride.



A Brief History of Portland

Before Meriwether Lewis and William Clark explored the area in 1805, Native Americans, such as the Chinook tribe, inhabited the Pacific Northwest long before white settlers arrived. Portland area landmarks — such as the Willamette River and Multnomah Falls — were named by these original inhabitants.

“Stumptown,” was an early (and enduring) nickname for the city because of the felled trees that dotted the town’s landscape. But the name, Portland, was decided by a coin-flip between merchant Francis Pettygrove from Portland, Maine, and lawyer Asa Lovejoy, from Boston, Massachusetts. Known as “The Portland Penny,” the copper piece is on display today at the Oregon Historical Society Museum.

The discovery of gold in California in 1849 opened the West Coast to immigrants from all parts of America and from Southeast China.

By 1850, Portland had about 800 residents. People who settled in the region made their living catching and selling fish, cutting timber and producing lumber, growing and harvesting wheat and raising cattle for market. When ship transportation between San Francisco and Portland began in 1851, Portland was incorporated as a city. Portland became a major transportation center because of its proximity to railroads and rivers. It became a stop for sailors who drank and caroused, most notably in the Old Town Chinatown district. There was a log-cabin hotel and a newspaper, the Weekly Oregonian. Portland was incorporated in 1851 and it has grown into the second largest city in the Northwest.

Oregon became the 33rd state to join the Union in 1859.

World War II changed Portland’s waterfront activities significantly, with the construction of hydroelectric power and local shipyards assisting with the war effort. Portland’s boom began when local ports started building cargo ships for Great Britain, and spread after the attack on Pearl Harbor with the construction of aircraft carrier escorts for the U.S. During that time, the region swelled with new residents and suburbs popped up to house them. Less than 100 years old, Portland suddenly had 360,000 inhabitants.

Though the city’s original planners developed the downtown with a gridded structure and small, easily traversed blocks. In an effort to preserve its natural beauty, in 1974, the city rerouted a major highway that had disconnected Portland from its waterfront and installed the 30-acre public Waterfront Park in its place. Next, in the late 1970s, Portland instituted an urban growth boundary, an artificial border that restricts development, inhibits sprawl and encourages green space around the city.

Portland history
Horse-drawn wagons were certainly the transportation of choice on Front Street in 1910; automobiles had not yet caught on in a big way. This view is south, probably at about Stark or Washington Street.

Sources: Travel Portland and www.pdxhistory.com





A word about recreational herb

Oregon legalized the recreational use of marijuana for those age 21+ back in July 2016. As a nonuser, I can say candidly that it hasn’t been that big of a deal. I don’t see people smoking it on street corners nilly-willy or bonging it up in city parks. Visitors CANNOT smoke it in public areas or in public view, they cannot smoke it in hotel rooms, in their cars or take it across state lines. There are certain Oregon cities where it is forbidden as well. Visitors CAN buy pot, edibles and whatever else they’ve done with it at state-licensed recreational marijuana retailers. It can be consumed on private property. For more information on the Dos and Don’ts, Travel Oregon has more information.

portland marijuana


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