Portland is a city of about 650,000 people laid out on the smallest downtown blocks in America. They measure 200 feet a side, roughly half the standard, which means twice as many corners, twice as many shopfronts and a downtown that is unusually pleasant to walk even in rain. That block size is not trivia. It is the reason the city feels dense and human at a scale that its population would not otherwise support.
The other thing Portland has, and almost nowhere else does at this scale, is the cart pods: clusters of permanent food carts occupying surface lots and corners, serving everything from Thai to Georgian khachapuri, at a fraction of restaurant prices. They move and change, so the specific pod matters less than being in the part of the city where they concentrate.
Where to be
Two areas, and they adjoin. Downtown, from the river up to about 12th Avenue, has the department stores, Powell's, the parks blocks and the majority of the hotels. The Pearl District, immediately northwest, is a converted warehouse quarter with the galleries, the breweries and a good deal of the eating.
Both sit on the west bank. The east side, across the Willamette, holds a lot of the city's best restaurants and its more interesting neighbourhoods, and it is a fifteen-minute walk or a short streetcar ride over a bridge.
Stay downtown or in the Pearl and you can walk to all of it, including the carts, the bookshop and the riverfront park, without ever getting into a car.
The ten below are grouped by which.
Downtown
Around the parks blocks, Pioneer Courthouse Square and the department stores.
The Nines, a Luxury Collection Hotel, Portland occupies the top floors of the old Meier & Frank department store, built around a nine-storey atrium, with a rooftop restaurant that has the best downtown view. It is the largest luxury hotel in the city.
The Nines, a Luxury Collection Hotel, Portland
Downtown · 4★ · $$$
Nine-storey atrium in the old department store
Check availabilitySentinel Hotel is the 1909 building with a terracotta facade and a bar in a former bank vault, and it has the most character of any hotel in Portland. Rooms vary between the two connected buildings.
Heathman Hotel sits beside the concert hall with a library-like lobby, a long-standing restaurant and the deepest service in the city. It is the traditional choice and it is well kept.
Heathman Hotel
Beside the concert hall · 4★ · $$
Library lobby and the deepest service in the city
Check availabilityKimpton Hotel Vintage Portland by IHG occupies a 1912 building with an art-and-design programme and rooms that are the most cheerful in Portland. It is a block from the parks blocks.
Kimpton Hotel Vintage Portland by IHG
Downtown · 4★ · $$
1912 building with the most cheerful rooms in town
Check availabilityDossier Hotel is the design conversion of a 1920s office building, with a good ground-floor restaurant and the most contemporary rooms downtown.
Hotel DeLuxe sits near the west end with a film-themed interior, a very good bar and rates that are the best value in the centre.
The Hotel Zags Portland occupies a position beside the parks blocks with bicycles for guests, a courtyard and a straightforwardly comfortable operation.
The Hotel Zags Portland
Parks blocks · 4★ · $$
Guest bicycles and a courtyard near the parks
Check availabilityThe Pearl District
The converted warehouse quarter northwest of downtown, with the galleries, the breweries and Powell's on its southern edge.
The Hoxton, Portland occupies a warehouse conversion with a large lobby that functions as a public living room, a rooftop restaurant and a basement bar. It is the most sociable hotel in the city and it sits between the Pearl and Chinatown.
The Hoxton, Portland
Between the Pearl and Chinatown · 4★ · $$
Rooftop restaurant and a basement bar locals use
Check availabilityWoodlark Hotel Portland, a Tribute Portfolio Hotel sits in the middle of the Pearl with a rooftop terrace, bikes for guests and the best position for the galleries and the Saturday market.
Woodlark Hotel Portland, a Tribute Portfolio Hotel
Downtown, Pearl edge · 4★ · $$
Best position for the galleries and the market
Check availabilityCanopy by Hilton Portland Pearl District occupies a corner near the Pearl's northern end with simple, well-priced rooms and a short walk to the breweries. It is the value pick in this quarter.
Canopy by Hilton Portland Pearl District
Pearl District · 4★ · $$
Short walk to the breweries at the best price
Check availabilityWhat we have left off
The east-side hotels are excluded, and they sit among the best restaurants in Portland. Most are converted motels, well designed and genuinely fun, and they are a bridge away from Powell's and the parks blocks.
What to do
Powell's City of Books occupies an entire block and holds over a million volumes. Allow more time than you think.
Eat at the carts, then eat properly on the east side, where most of the city's serious kitchens are. Portland's food is the reason to come and it is concentrated in Buckman, Kerns and along Division and Alberta.
Walk or cycle the Waterfront Park loop, and the Eastbank Esplanade across the river. Portland's bike infrastructure is the best in the country and hiring one for a day is straightforward.
Go to the Japanese Garden and the Rose Garden in Washington Park, both excellent and both above the city. Then leave: the Columbia River Gorge and Multnomah Falls are 40 minutes east, Mount Hood 90, and the coast at Cannon Beach 90 minutes west.
Coffee and beer, both of which Portland does better than almost anywhere.
Practical notes
The airport connects on the MAX light rail to downtown in about 40 minutes for a few dollars.
June to September is dry, warm and the best window by a wide margin. October to May is grey with persistent light rain rather than downpours. The rain is the price of the green.
There is no sales tax in Oregon, which makes shopping meaningfully cheaper. Hotel parking runs 40 to 50 dollars a night and a car is unnecessary until you leave the city.
Explore 4 & 5 Star Portland Hotels
Questions people actually ask
Downtown or the east side?
Downtown or the Pearl for hotels and walkability. The east side has the better restaurants and few good hotels; walk or take the streetcar over.
Is the rain a problem?
It is persistent and light rather than heavy. Locals do not use umbrellas. It also stops almost entirely from June to September.
Are the food carts still a thing?
Yes, though the pods move as lots get developed. Ask at your hotel which are currently operating rather than relying on an older list.
How many nights?
Three in the city, four or five with the Gorge and the coast.