Shakespeare once wrote, "Methinks there is nothing better than free food / except, perhaps, for a hypothetical kind of free food / that doth also be stuffed full of cigarettes and pornography." While Shakespeare's "dream food" is not yet a reality, free food is all around us in tiny, sample-sized pieces. Walking through Portland and stealing them is a fun way to spend a sunny day outside; it also makes for a great first date activity, and says to your potential mate, "I may be cheap, but you will delight in my irreverence."
•Peak hours are 12-4 pm. This is when you'll find the most excellent samples.
•The best ones are usually at deli and bakery counters. Learn when the workers change their shifts so that you can sample, "shop" for five minutes, then come back to sample again.
•Be confident that what you're eating is actually a sample. I once consumed $15 worth of chocolate-covered strawberries before I was informed that they'd just been set out to dry.
•Learn from the kangaroo and the squirrel: Your pockets and cheeks can be used to store extra samples.
ZUPAN'S Both the Zupan's on W Burnside and on NE Belmont are excellent. There's usually something out all the time (even at 2 am), and during peak hours I've had some remarkable sampling experiences. On one heavenly afternoon a few summers back, the Burnside store was actually giving out little tubs of pasta, smoked salmon, delicious brownies, and whole pieces of sushi all at once. Unfortunately, I ate to the point of being "asked to leave" and couldn't return for quite some time. This experience illustrates another important issue: the eastside Zupan's is bigger, and thus better for anonymity.
TRADER JOE'S Trader Joe's locations are a safe bet, as many of them have "tasting stations" where you can count on some no-nonsense sampling. The food itself is often mediocre--last time, I found only tortilla chips, chocolate wafers, and lemonade--but on the plus side there are rarely any employees in sight, allowing you to really go ape-nuts. Occasionally they'll have someone preparing hot samples, in which case you'll need to employ specialized techniques like "misdirection," "palming," and "trained goose releasing" to procure yourself more than one.
WHOLE FOODS Whole Foods was a tasters' paradise when it first opened, and still can be if you hit it at the right time. The pizza samples are highly coveted (three of them = an entire slice), but are hard to come by. They regularly put out fruit samples, which offer a much-needed respite from the pounds of chips and dip that you've managed to consume.
WILD OATS (formerly NATURE'S)
Wild Oats runs hot and cold in terms of consistency, but when you strike it rich, the food will surely be quality. Their samples can be more disguised than most; for example, the Wild Oats on E Burnside always has tiny cups for tasting their coffee, but these cups are not in an eye-catching place. You are tricky, Wild Oats, but I am trickier.
FRED MEYER I still remember walking through the aisles of Fred Meyer with my mother when I was young, and it seemed that around every corner there was another little old lady with a toaster oven handing me a warm sample. Sadly, since their merger with Kroger foods a few years ago, Fred Meyer's samples have turned to crap. Do not waste any time there.
OTHER PLACES Go to the Uptown Elephant's Deli on the right afternoon, and you'll be sampling west hills-style. Then go next door to Ben & Jerry's, ask for three tastes at once, and slip away while they're helping someone and you're "deciding." The food court in Pioneer Place has a lot of Asian-themed places, all of which will give you pieces of chicken on toothpicks. Costco is far away, and you have to be a member to access their special world of popcorn by the pound and $10 Britney CDs, but if you can get in you'll be privy to a buttload of totally unsupervised samples.
Good luck, skimmers of Portland!