We'd started with breakfast at Pine State Biscuits, part of the Alberta Arts District that has sprung up in this northeast part of Portland, eating our biscuits and gravy at picnic tables in the restaurant's side yard.
Lunch was chicken burritos at the food-cart pod in the Mississippi neighbourhood – just a tiny constellation among the 642 food carts in the Portland area – and a stroll past shops filled with antiques, bikes and local-designer clothing.
Late-afternoon beer: The LaurelThirst Public House, where we sat at tables on the sidewalk in the mostly residential Kerns neighbourhood listening to a bluegrass band playing inside. Dinner was at a small Italian place, part of a small cluster of restaurants and shops tucked in among the grand old houses and apartment buildings of Southeast Belmont.
Every one of these experiences – rare or impossible in Vancouver – made me envy Portland once again for several reasons.
One is its beautiful stock of historic housing. Imagine a Vancouver devoid of Vancouver specials and filled instead with the arts and crafts houses of Kitsilano and Edwardians of Mount Pleasant.
(Alas, not much Vancouver can to do replicate that at this late date. Portland is lucky in having undergone a massive building boom in the early 20th century.) But there are two things this so-similar city has that we don't, although we could.
One is a high level of small-business innovation. Another is a sense of economic creativity and identity in all of its neighbourhoods.
In Vancouver, a huge number of the interesting restaurants and shops are concentrated in the downtown or, at best, neighbourhoods right next to downtown.
South of 16th and west of Victoria, the city is almost suburban, with commercial strips that are dominated by bread-and-butter service shops, unambitious ethnic restaurants, and ubiquitous chains.
The story of bars and food carts in the two cities highlights the differences. In Vancouver, 70 per cent of all the city's bars are downtown, as are almost 100 per cent of the food carts, contributing to a sense that this is a city focused on serving visitors, rather than on creating an interesting quality of life in all neighbourhoods.
That's a far cry from Portland, which has any number of small local pubs in the middle of residential districts, like LaurelThirst, while several food-cart pods have sprung up on the east, non-downtown side of the river like the Mississippi Avenue district.
Portland's business climate has the advantage of low real-estate prices, which allow people to experiment more easily, and a more homogeneous population, which makes marketing easier.
But those aren't the only factors that make the difference.
City hall has a department dedicated to neighbourhoods that recently produced a plan for neighbourhood economic development.
And its agencies have a policy of keeping rules to a minimum.
Food carts have to meet basic health requirements, but nothing else – no judging panels, no numbers restrictions.
"It's really the market that dictates," says Ben Duncan, the Multnomah County health official whose department issues health permits, which can come in as little as two months.
For bars, getting a licence is a simple matter of applying to the state. There is no limit on the number of licences and the city has no say, other than zoning requirements. Neighbours get canvassed to see if they have strong objections, but that's it.
The result: Vancouver has 283 liquor-primary licences, with new ones approved at a rate of about five a year. Portland has 168 licensed brewpubs alone, not to mention a couple hundred more regular pubs, bars, lounges and more.
"In my experience, it takes two to three months to get a licence," says Bruce Bauer, owner of the Vino wine store in Portland. "There isn't a hindrance."
As a result, he's about to open a new wine bar in a little strip of stores on 28th in Laurelhurst. Another new venue to explore next time – and one more reason to envy Portland.