Portland Itineraries

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Portland rewards people with the patience to 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 can match the Rose City’s beauty.

Located between snow-capped Mt. 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.

Portland is 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.

Start your Portland exploration 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 living room. On most days, the walk is perfect for bike riding, jogging or strolling along the Willamette River. But in the spring and summer, the park becomes a focal point for festivals, hosting the largest Cinco de Mayo celebration in North America as well as the Portland Rose Festival and Grand Floral Parade, Waterfront Blues Festival, and Oregon Brewers Festival. A notable favorite is The Big Float in late July, where thousands of partiers grab an inner tube, raft or other inflatable curiosity and go for a giggling splash in the Willamette River.

At the northern end of the park on the weekends, visitors will find the 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. It also has breathtaking vistas of Mt. Hood and the still-active volcano, Mount St. Helens, which blew its top and rained ash on the Rose City in 1980. At the southern end of the walkway, you can rent kayaks and go for a peaceful paddle.

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.


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