Portland Maine: Walking Food Tour with Donuts & History

Summary

Portland’s donut legends, waterfront walks, and local stories blend together

You’ll wander Portland’s Old Port with a local guide, sampling six fresh donuts (from classic Maine potato to Asian-inspired yeast) while hearing quirky stories behind each bite. Skip long lines, sip coffee or water, meet bakers along the way—and leave with sticky fingers, new friends, and probably a craving you won’t shake soon.

What’s the experience like?

The first thing that hit me was the smell—like someone left a bakery door open just for us. We started right near the waterfront in Portland, Maine, and I could hear gulls arguing over scraps while our guide (I think her name was Sarah?) handed out these little paper bags. She grinned and said, “You’ll want to eat this one warm.” It was a Maine potato donut—soft but somehow dense too, and the chocolate glaze actually tasted like chocolate. I didn’t expect it to be that good. The street outside was still damp from last night’s rain so my sneakers squeaked on the cobblestones as we walked.

Sarah had all these stories about sea captains and prohibition—she made Portland’s history sound kind of wild. At one stop she pointed out a plaque for Hanson Gregory (the guy who supposedly invented the hole-in-the-middle donut). I tried to repeat his name with her accent but butchered it; she laughed and said most people do. We got to skip a line at The Holy Donut that stretched halfway down the block—felt like cheating in the best way. Those donuts are famous for a reason but honestly? The tiny ones at the next place were still warm from the fryer and had this cinnamon sugar that stuck to my fingers for ages. I can still smell it when I think back.

The walk itself was only about a mile but there were moments where I forgot we were even moving—just listening to Sarah talk about immigrants bringing recipes over or watching locals wave at her like they knew she’d be back tomorrow. There was this quick moment by an old brick warehouse where everything went quiet except for someone rolling barrels inside (or maybe it was kegs?). The air tasted salty and sweet at once. By the end, I had more donut than sense and a list of places to check out later scribbled on my phone. Still not sure how I’m supposed to pick a favorite.

Step-by-step itinerary

Day 1 — Portland walking food and history tour

• Meet local storyteller guide
• Skip lines at The Holy Donut
• Sample two Maine potato donuts
• Walk scenic one-mile waterfront loop
• Hear Portland history stories
• Sample two artisanal bite-sized donuts
• Visit two more award-winning bakeries
• Sample two Asian inspired yeast donuts
• Meet donut makers and learn secrets
• Receive insider tips for local spots

Top questions

How long is the Portland walking food tour?

The tour lasts around 90 minutes and covers about one mile through Portland’s Old Port district.

How many donut samples do you get on this tour?

You’ll try six hand-picked donut samples from three award-winning bakeries during the tour.

Does the tour include drinks?

Coffee or water is included with your donut tastings on this walking food tour.

Is there a lot of walking involved?

The route is about one mile on foot through historic areas with some uneven surfaces like cobblestones.

Are there any line skips at popular bakeries?

Yes, you’ll skip the line at The Holy Donut as part of your guided group experience.

Can infants or small children join?

Infants and small children can ride in prams or strollers during the tour.

Are service animals allowed on this tour?

Yes, service animals are welcome throughout the walking food tour in Portland.

What’s included

Your day includes all fees and taxes, six fresh donut samples across three bakeries (with options like Maine potato donuts), coffee or water with your tastings, plus lively stories from your local guide as you stroll through historic Portland’s Old Port district before finishing up with tips for more spots to explore on your own.