Portland Downtown Food Tour: 6 Tastings & Brewery Stop

Summary

Portland downtown food tour with brewery stop and global flavors

You’ll wander downtown Portland with a small group, starting at Pioneer Square and tasting everything from Japanese-inspired sandwiches to Southern shrimp and grits (or veggie options). You’ll dip warm pretzels in tangy sauces at an iconic brewery, try a surprise dish only revealed on tour day, and finish with inventive pie from a local bakery. It’s relaxed, social, full of flavors — with moments you’ll remember long after.

What’s the experience like?

The first thing I noticed in Pioneer Courthouse Square was the sound — shoes scuffing brick, a busker’s guitar echoing off the old courthouse, and our guide waving by the Umbrella Man statue. She had this easy way of making everyone feel like we’d met before. I didn’t expect to learn so much about Portland just standing there, but she pointed out little things — like how locals call it their “living room” — that made me see the city differently already.

Our first bite was this Japanese-style sandwich, warm and crispy with miso that hit that salty-sweet spot. I tried to say its name right (Li laughed when I butchered it), but honestly, I was too busy chewing. Walking between stops, you catch whiffs of coffee from somewhere nearby and hear snippets of conversations about bikes or books. The shrimp and grits came next — creamy, peppery, Southern comfort in a bowl. One of the group swapped for fried green tomatoes (she said they were just as good), which is nice if you’re vegetarian.

I liked how nothing felt rushed; we wandered into a brewery where it smelled like yeast and hops (in a good way). The pretzel was soft, still warm, with these tangy dips that made me wish I could eat slower. If you add the beer tasting, you get why people call Portland one of America’s top beer cities. There was this secret dish too — they won’t tell you what it is ahead of time (I won’t spoil it), but it felt very “Portland.”

The last stop was dessert: a slice of pie that somehow managed to be both gluten- and dairy-free without tasting like cardboard. It was tart and sweet at once — seasonal fruit, I think? The bakery owner waved from behind the counter as we left; she seemed proud. I still think about that pie sometimes when I walk past bakeries back home. So yeah, if you want a day trip in Portland that feels like someone showing you their favorite spots instead of just ticking boxes… this food tour is it.

Step-by-step itinerary

Day 1 — Portland Downtown Food Tasting Tour

• Meet at Pioneer Courthouse Square
• Introduction to Portland’s history and culture
• Taste Japanese-inspired miso sandwich
• Enjoy Southern-style shrimp and grits
• Taste soft pretzel at iconic brewery
• Try special Secret Dish surprise
• Finish with gluten- and dairy-free pie

Top questions

Where does the Portland Downtown Food Tour start?

The tour starts at Pioneer Courthouse Square next to the Umbrella Man statue.

How many tastings are included on this food tour?

You’ll enjoy six different tastings during the tour.

Is there a vegetarian option for the shrimp & grits?

Yes, vegetarians can have fried green tomatoes instead.

Does the tour include drinks or alcohol?

A drink upgrade is available for local craft beer tasting at one stop.

Are dietary requirements accommodated?

You should contact in advance so dietary needs can be arranged where possible.

How long is the walking distance on this tour?

The tour involves a fair amount of walking through downtown Portland; comfortable shoes are recommended.

Is public transportation available near the starting point?

Yes, public transportation options are available close to Pioneer Courthouse Square.

What is included in the price of this food tour?

The price includes all tastings plus water; beer tasting is an optional upgrade.

Will we know what the secret dish is before booking?

No—the secret dish remains a surprise until revealed during your tour.

What’s included

Your day includes all six tastings—like Japanese-style sandwiches with savory miso seasoning, Southern-style shrimp and grits or fried green tomatoes for vegetarians, a warm soft pretzel with creamy dips at an iconic brewery (plus optional craft beer tasting), water throughout the experience, a special Secret Dish revealed on tour day itself, and finally a gluten- and dairy-free seasonal pie from a beloved local bakery before heading off on your own again downtown.