Portland Walking Food Tour: Skip-the-Line Donuts & History

Six donuts, one mile of cobblestone streets, and the story of how Maine invented the hole in the middle

A 90-minute walking food tour through Portland's Old Port where you skip the line at The Holy Donut and two other local bakeries, sample six Maine potato and artisanal donuts, and hear a local guide's stories about sea captains, Prohibition, and the immigrant sailor credited with inventing the modern donut. Small groups, water included, all fees covered.

The experience

You've got a couple of hours free in Portland and you want to eat something worth remembering. This tour starts at the working waterfront and loops through the Old Port's cobblestone streets: a one-mile walk guided by someone who actually knows the place. The guide meets you, walks you straight past the line at The Holy Donut (the one that made it into The Boston Globe), and has the donuts waiting. No queue, no standing around hungry.

You'll sample six donuts across three stops: Maine potato donuts with dark chocolate cake that tastes nothing like what you expected; warm artisanal bites straight from the fryer with toppings that change with the season; and Asian-inspired raised yeast donuts that are just fluffy and sweet. Between tastings, the guide tells you why a Maine potato donut is different (what the potato actually does to the texture), and walks you through the actual history: sea captains, Prohibition, and the specific immigrant sailor who figured out the hole-in-the-middle trick way back. Water is included. By the end you'll have insider tips for breweries and restaurants to hit after, and you'll know which photo spots in the Old Port actually work.

The walk is one mile on uneven wharf and cobblestone, so you need to be comfortable on that kind of ground. The whole thing takes 90 minutes. Groups stay small, which means the guide can actually talk to you instead of shouting at a crowd.

What’s included

• Six hand-picked donut samples at three award-winning bakeries with skip-the-line access at The Holy Donut.
• water.
• a 90-minute guided walk through the Old Port with a local storyteller.
• insider tips for breweries, restaurants, and photo spots to explore after the tour.
• all fees and taxes.

Before you book

Days and timesThursday to SundayDepartures at 09:30 and 11:30Last departure this season: 30 Nov

Book up to1h before

AgesAdult (12 and older) · Child (under 12)

GroupUp to 12

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Moderate physical effortStroller-friendlyPets welcome

Operated by The Maine Donut Tour

Is this one for you?If you land in Portland with a free afternoon or a couple of hours between plans, this tour solves the problem of not knowing which donut shop is actually worth the line or what the city's history actually is. The guide does the routing and the timing, so you taste the best of it without building the day yourself.

Traveler reviews

4.80★★★★★★★★★★

244 verified traveler reviews

5 ★215

4 ★15

3 ★10

2 ★2

1 ★2

Read all the reviews ›

Top questions

Can children come?

Yes. Ticket types: Child (under 12).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What exactly do I get to taste on this Portland donut tour?

You sample six donuts total: two Maine potato donuts with dark chocolate cake, two fresh-made artisanal bite-sized donuts warm from the fryer with seasonal toppings, and two Asian-inspired raised yeast donuts. Water is included with all tastings.

Do I really skip the line at The Holy Donut?

Yes. The guide arranges for the donuts to be ready when your group arrives, so you walk straight to the counter without waiting. The other two bakeries are local favorites that don't draw the same crowds.

How long is the walk and what's the ground like?

The tour covers one mile looping from the working waterfront through the Old Port. The route includes uneven wharf surfaces and cobblestone streets, so you need to be comfortable walking on that kind of ground. The whole tour takes 90 minutes.

What's the story about Maine and the invention of the donut?

An immigrant Maine sailor is credited with inventing the hole-in-the-middle donut. Your guide tells that story along with other bits of Portland history (sea captains, Prohibition, and how the city's past shaped what it is now), while you walk the Old Port.

What do I need to bring or wear?

Wear comfortable walking shoes suitable for cobblestone and uneven surfaces. Water is provided. All fees and taxes are included in the price, so there's nothing extra to pay at the bakeries.