Walking Tours

PORTLAND

10 Best Walking Tours In Portland

Portland's standouts, both coasts.

The 10 standout walking tours a Portland traveller will actually book. What each one covers, who runs it, and what it costs from the dock or the trailhead.

10 Best Walking Tours In Portland

Portland’s Original Delicious Donut Adventure & Walking Food Tour

Portland's Original Delicious Donut Adventure & Walking Food Tour - Sesame Donuts and Coco Donuts: The Best Way to Start Hungry

1.Portland’s Original Delicious Donut Adventure & Walking Food Tour

Most Popular★ 5.0

Walk Portland’s donut scene with a local guide, tasting at shops and ending at Voodoo. Vegan and gluten-free options.

“Be ready for a sugar overload! Yummy choices, an opportunity to try something new while walking around downtown. Eric was great, friendly and informative and since there were only two of us, he was very accommodating. Tried places I would not have gone to, and Voodoo Doughnut is in the tour, too!”

533 reviews2 hours (approx.)From $69.00by Underground Donut Tour - Portland

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Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour - From Post Office Park to Bell Buoy Park: where you’ll walk

2.Portland, Maine: Hidden Histories Guided Walking Tour

★ 5.0

Portland hidden histories walking tour with Dugan. Small-group, funny storytelling across Downtown, Old Port, and Commercial Street.

“Unfortunately I was unable to make to the tour due to immigration check in from the cruise. Unable to reschedule or obtain a refund. Tour guide did try to get me on your even late.”

514 reviews2 hours (approx.)From $54.00by Portland by the Foot

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A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland - Old Port Highlights: From the U.S. Custom House to Longfellow’s Footprints

3.A Walk Through Time Tour in Portland

★ 5.0

A 2-hour Portland Maine walking tour with a local guide, small groups, and included snacks. See Old Port lobster sites and more.

“Portland history tour in the winter! Ross was fantastic and made learning about this great city memorable. Best walking tour, even with frigid temps!”

496 reviews2 hours (approx.)From $48.99by Maine Day Ventures

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Old Port Culinary Walking Tour from Portland

Old Port Culinary Walking Tour from Portland - Old Port tastings: fish tacos, chowder choices, lobster roll, and seafood market bites

Intro to Portland Small Group Walking Tour

Intro to Portland Small Group Walking Tour - Timing, Small-Group Size, and How to Choose a Start Time

5.Intro to Portland Small Group Walking Tour

★ 5.0

A 2–2.5 hour small-group walk through downtown Portland’s parks, architecture, and public squares with a certified local guide for $29.

“This Portland History tour was fun and informative (our tour guide was very knowledgeable and pleasant).”

300 reviews2 hours to 2 hours 30 minutes (approx.)From $29.00by Around Portland Tours

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Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

Portland Walking Food Tour – Warm Donuts, History & Hidden Gems - What You Actually Taste: Potato Donuts, Chocolate Cake, and More

6.Portland Walking Food Tour – Warm Donuts, History & Hidden Gems

★ 5.0

Portland walking food tour with Holy Donut skip-line stops, six Maine donut samples, and local history on a scenic Old Port walk.

“This was a great tour to start our day off. Renee was a great guide! Not only did we sample some great treats, but we learned about Portland's history, culture, architecture, and got some intel about great places to eat & visit. We did the 9:30 am tour, which ended with enough time to grab…”

179 reviews2 hours (approx.)From $79.00by The Maine Donut Tour

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Old Port “Seafood Lovers” Walking Lunch Tour in Portland, Maine

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine - The Lobster Roll and Chowder Stops: The Maine Stuff You’ll Actually Remember

7.Old Port “Seafood Lovers” Walking Lunch Tour in Portland, Maine

★ 5.0

Old Port Seafood Lovers walking lunch in Portland: lobster roll, chowder, beer, lobster-fishing stories, and a sweet finish.

“Ray was amazing. Extremely knowledgeable and personable. I’d do the tour again just for him. I learned so many new things regarding the history of food and Portland.”

148 reviews3 hours (approx.)From $159.99by Maine Day Ventures

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Portland, Maine: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour - Where you start and how the route will feel

8.Portland, Maine: Black History Guided Walking Tour

★ 5.0

Portland, Maine Black history walking tour with Dugan. Small group, iconic stops, Underground Railroad stories, and donation to Abyssinian Meeting House.

“Dugan was amazing with historical knowledge and the ability to answer questions appropriately. Recommend this as a must do. If it is in the colder season layer and bundle up because you will want to give your full attention.”

141 reviews2 hours (approx.)From $54.00by Portland by the Foot

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Portland Pizza Walking Tour: 4 Stops, Full Slice Each

Portland Pizza Walking Tour: 4 Stops, Full Slice Each - Stop 1 at 2174 W Burnside St: start with a Portland classic

9.Portland Pizza Walking Tour: 4 Stops, Full Slice Each

★ 5.0

Four Portland pizza styles, four full slices, a ~1-mile walk in about 2 hours, with local guide Beau and neighborhood food tips for $75.

“All of the pizzas were delicious, and the host (Beau) was very friendly and knowledgeable! We really enjoyed the whole experience and will definitely be booking more tours in the future.”

58 reviews2 hours (approx.)From $75.00by AFK Food Tours

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Audio Guided Walking Tour from Old Port of Portland, Maine

Audio Guided Walking Tour from Old Port of Portland, Maine - Longfellow’s neighborhood stop and the outside-of landmark approach

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