Your adventure begins at Sesame Donuts, located near the South Park Blocks, one of Portland’s oldest and most iconic green spaces. As you savor their fresh, handcrafted donuts, you’ll learn about the history of this lush, tree-lined park. Originally established in the mid-19th century, the South Park Blocks were designed to bring a touch of nature to the city and have since become a cultural and recreational hub, surrounded by museums, theaters, and historic landmarks. Next, we’ll head toward Pioneer Square, often called Portland’s “Living Room.” Along the way, we’ll stop at a neighborhood café that expertly blends modern donut-making with Portland’s signature coffee culture. Here, you’ll taste the perfect harmony of sweet and caffeinated, a pairing that reflects the city’s love for local, artisanal craftsmanship. From there, it’s off to the original location of the legendary Voodoo Doughnuts, a Portland icon known for its quirky vibe and even quirkier creations. While you bite into a Bacon Maple Bar or a Voodoo Doll donut, we’ll recount the story of how this offbeat shop put Portland on the map as a must-visit destination for donut lovers and helped define the city’s reputation for embracing the unconventional. Our final stop is at the bustling Pine Street Market, where a boutique stand offers bite-sized donuts that pack big flavors. While you enjoy these warm, freshly prepared treats, we’ll discuss the history of Pine Street Market itself, a historic building now home to a variety of Portland’s most innovative food vendors. This tour offers not just delicious donuts but also a glimpse into the city’s vibrant history and creative spirit. It’s the perfect way to taste your way through Portland’s past and present, one sweet bite at a time.