Portland, Maine’s best walking tours pack big value into compact experiences. The informative Old Port Culinary tour combines local history with generous food tastings at family-run establishments – it’s our favorite for first-time visitors.
History buffs will appreciate the Hidden Histories walk through Portland’s centuries-old streets and stories. For those short on time, the Intro to Portland Small Group tour efficiently covers main highlights in just two hours.
The Old Port “Seafood Lovers” tour stands out for sampling the city’s famous fresh catches, while craft spirit enthusiasts should consider the Distillery Row tour on Portland’s bustling Eastside. Self-guided options work well for independent explorers.
Let’s look at our top-rated walking tours in detail…
Good To Know
- The Old Port Culinary Walking Tour offers an immersive exploration of Portland’s historic Old Port neighborhood with lunch tastings at 5-6 local eateries.
- The Portland, Maine Hidden Histories Walking Tour takes visitors on a 2-hour journey through the city’s storied past and offers a donation toward restoring the Abyssinian Meeting House.
- The Intro to Portland Small Group Walking Tour provides a rundown of the city’s highlights, led by a certified guide and departing from the conveniently located Director Park.
- The Portland Walking Food Tour with Secret Food Tours offers a meal-sized tasting experience, exploring top food destinations and indulging in must-try bites.
- The Craft Breweries of Portland Walking Tour explores the city’s renowned craft beer scene, including coffee, tea samples, and snacks, with a maximum of 12 travelers.
Old Port Culinary Walking Tour From Portland
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This popular Old Port Culinary Walking Tour from Portland offers food lovers an immersive exploration of the city’s historic Old Port neighborhood. With 96% of travelers recommending the tour, it’s a must-do for those seeking to sample Maine-inspired cuisine.
Led by a knowledgeable guide, the tour takes visitors to 5-6 local eateries, where they can enjoy lunch tastings. The experience provides a more intimate setting, with a maximum of 14 travelers. Guests will discover traditional and local fare, while learning the stories and secrets behind Portland’s culinary stalwarts.
The tour concludes at a nearby ice creamery or Deans Sweets, leaving participants with a sweet ending to their gastronomic adventure.
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This popular Old Port Culinary Walking Tour from Portland offers food lovers an immersive exploration of the city’s historic Old Port neighborhood. With 96% of travelers recommending the tour, it’s a must-do for those seeking to sample Maine-inspired cuisine.
Led by a knowledgeable guide, the tour takes visitors to 5-6 local eateries, where they can enjoy lunch tastings. The experience provides a more intimate setting, with a maximum of 14 travelers.
Guests will discover traditional and local fare, while learning the stories and secrets behind Portland’s culinary stalwarts.
The tour concludes at a nearby ice creamery or Deans Sweets, leaving participants with a sweet ending to their gastronomic adventure.
Read our full review: Old Port Culinary Walking Tour From Portland Review
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2 Hours Portland, Maine Hidden Histories Walking Tour
The Hours Portland, Maine Hidden Histories Walking Tour takes visitors on a captivating two-hour journey through the city’s storied past. Highly recommended by 100% of travelers, this tour offers a donation toward restoring the Abyssinian Meeting House, America’s third-oldest standing Black church.
With a maximum of 15 travelers, the tour is wheelchair and stroller accessible, and service animals are welcome. While Portland is a hilly city with some cobblestones, stairs, and uphill walking, the tour’s accessible surfaces and transportation ensure a comfortable experience.
Guests can also enjoy a 10% discount on water tours with Portland Paddle after the walking tour. This Badge of Excellence-awarded experience showcases Portland’s rich history and culture in an engaging and accessible manner.
Read our full review: 2 Hours Portland, Maine Hidden Histories Walking Tour Review
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Intro to Portland Small Group Walking Tour
Visitors embark on a captivating exploration of Portland’s vibrant heart through the Intro to Portland Small Group Walking Tour. Led by a certified guide, this 94% recommended tour offers a rundown of the city’s highlights.
The walking tour departs from the conveniently located Director Park, meeting near the paved fountain. Covering a maximum of 30 travelers, the experience is wheelchair and stroller accessible, making it inclusive for all.
Along the way, participants learn about Portland’s history and culture, with gratuities for the guide always appreciated. The tour concludes back at the starting point, leaving guests with a deeper appreciation for this vibrant Pacific Northwest destination.
Read our full review: Intro to Portland Small Group Walking Tour Review
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Old Port “Seafood Lovers” Walking Lunch Tour in Portland, Maine
Amidst Portland’s vibrant culinary scene, the Old Port “Seafood Lovers” Walking Lunch Tour offers a delectable exploration of the city’s maritime heritage. Participants will savor a fresh lobster roll, indulge in New England or seafood chowder, and sip on Maine craft beer or soda.
The tour covers the lively Old Port and Waterfront District, showcasing restaurants, pubs, markets, and artisanal shops. With a knowledgeable guide, travelers will learn about the local lobster industry and sample the region’s signature seafood delicacies. Highly recommended by 92% of past visitors, this tour promises an immersive culinary experience that celebrates Maine’s coastal flavors.
Read our full review: Old Port “Seafood Lovers” Walking Lunch Tour in Portland, Maine Review
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Portland Walking Food Tour With Secret Food Tours
A Secret Food Tour provides a delectable exploration of Portland’s vibrant culinary scene. Discover the city’s top food destinations, indulging in a variety of must-try bites, from the Yolko Onno Sandwich to Ramen and the iconic Simpsons Donut. Along the way, savor local coffee and uncover a secret dish that will delight your taste buds.
Led by knowledgeable guides, the small-group tour explores locals-loved destinations, offering a meal-sized tasting experience. Rated highly by travelers, this tour earns a Badge of Excellence and is easily accessible via public transportation.
Whether you’re a foodie or simply seeking a unique adventure, the Portland Walking Food Tour promises to immerse you in the dynamic flavors of this vibrant city.
Read our full review: Portland Walking Food Tour With Secret Food Tours Review
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Buckman Neighborhood Walking Tour – Portland
Tucked away in the heart of Portland, the Buckman Neighborhood Walking Tour offers a captivating exploration of the city’s vibrant and hipster-friendly district. Led by a local guide, this small-group tour takes visitors on a delightful journey through the neighborhood, highlighting top international restaurants and food pods serving up tantalizing treats.
Travelers can indulge in a delectable lunch and food samples, all while learning about the area’s rich history and thriving culinary scene. The tour culminates at the Hawthorne Asylum Food Cart Pod, where guests can further savor the neighborhood’s diverse flavors. With its exceptional reviews and the tour company’s Badge of Excellence, this walking adventure is a must for anyone seeking an authentic taste of Portland’s Buckman neighborhood.
Read our full review: Buckman Neighborhood Walking Tour – Portland Review
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Guided Walking Tour of Downtown Portland, Oregon
What better way to explore the heart of Portland, Oregon than through a guided walking tour of the downtown area? The 2-hour tour, recommended by 94% of travelers, covers the city’s green spaces, parks, and provides historical and cultural information.
Led by Peak Tours and Transit, the tour departs from the iconic Pioneer Courthouse Square at 10:00 am and ends near the Salmon Street Springs, with the guide offering to direct participants back to the starting point. Accessible to wheelchair and stroller users, and welcoming service animals, this private tour is a great way to discover downtown Portland’s highlights.
Conveniently located near public transportation, it’s an insightful and efficient city exploration.
Read our full review: Guided Walking Tour of Downtown Portland, Oregon Review
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Craft Breweries of Portland Walking Tour
Portland’s vibrant craft beer scene takes center stage on this 1.5-hour walking tour. Explore the city’s renowned makers and artisans as you visit local breweries, sample craft beers, and learn about the brewing process.
The tour includes coffee, tea samples, and snacks, ensuring a well-rounded experience. Conveniently located near public transportation, the tour starts and ends at 833 SE Main St, allowing you to continue your exploration of Portland’s thriving beer culture.
With a maximum of 12 travelers, this small-group experience provides an intimate and personalized look at the city’s craft brewing scene. Free cancellation up to 24 hours in advance makes planning a breeze.
Read our full review: Craft Breweries of Portland Walking Tour Review
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Portland Small-Group Foodie Brunch Walking Tour
Savor the flavors of Portland’s vibrant food scene on this 2.5-hour foodie brunch walking tour. Led by a passionate local guide, you’ll explore the charming Mississippi neighborhood and indulge in a delicious brunch at 12 highly rated establishments.
With 12 rave reviews and a 100% recommendation rate, this tour is a must for anyone seeking an authentic taste of Portland. Along the way, you’ll learn about the city’s rich culinary history and culture.
The tour covers a distance of just 0.6 miles, making it an easy and enjoyable stroll. With a maximum group size of 10, you’ll enjoy a personalized experience. Book this tour for a memorable exploration of Portland’s vibrant food scene.
Read our full review: Portland Small-Group Foodie Brunch Walking Tour Review
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Audio Guided Walking Tour From Old Port of Portland, Maine
This audio-guided walking tour of Portland’s historic Old Port district offers an immersive and flexible experience. With 24 reviews and a Badge of Excellence, the tour can be accessed anytime, allowing you to explore at your own pace.
Starting at the iconic Piece of the Berlin Wall, the tour navigates through the charming Old Port, ending at the historic Mariners Church. Available daily from June 2023 to December 2025, this private tour provides an accessible and affordable way to discover Portland’s rich maritime heritage.
Enjoy the convenience of no expiration and free cancellation up to 24 hours before the tour start, ensuring a seamless and enjoyable experience.
Read our full review: Audio Guided Walking Tour From Old Port of Portland, Maine Review
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Macabre Ghost History of Portland, Oregon Walking Tour
Discover Portland’s darker past on this captivating Macabre Ghost History walking tour. Explore the city’s macabre ghost history with a guided walking tour that takes you through the streets and reveals the untold stories of prominent people. Learn fascinating information not commonly known about Oregon and Portland as you visit historic sites.
The tour includes snacks and a recommendation for ice cream or treats, though the cost isn’t included. Gratuities for the guides are appreciated. The tour meets at Revolution Hall and ends at Lone Fir Cemetery, with guides available to assist with navigating back to the starting point. With a maximum of 14 travelers, this walking tour is a must for those interested in Portland’s chilling past.
Read our full review: Macabre Ghost History of Portland, Oregon Walking Tour Review
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Smartphone-Guided Walking Tour of Downtown Portland
With the help of a smartphone, explore the heart of downtown Portland on this self-guided walking tour. Discover family-friendly stops and engage with interactive questions along the way.
The easy-to-use web interface makes navigation a breeze, and the tour is accessible for wheelchair users and stroller-pushers alike. Starting at the convenient meeting point near the MAX light rail, the 2-hour experience culminates at the iconic Bill Naito Legacy Fountain.
Available seven days a week, this private tour offers flexibility to explore at your own pace. At $27.50 per group of up to 15, it’s an affordable way to uncover the highlights of downtown Portland.
Read our full review: Smartphone-Guided Walking Tour of Downtown Portland Review
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Self Guided Solo “Weird and Wonderful Portland” Walking Tour in Old Town
Set out on a captivating self-guided solo exploration of Portland’s Old Town with this “Weird and Wonderful” walking tour. Smartphone-guided via the WalknTours app, the tour starts at Old Town Pizza and ends at the iconic Keep Portland Weird sign behind Dante’s.
Discover the dark past of Old Town Pizza and its connection to the infamous “Shanghai Tunnels.” Stop at the renowned Voodoo Donuts, and soak in the unique atmosphere of this eclectic neighborhood.
While the tour isn’t wheelchair-accessible, it’s stroller-friendly and accessible via public transportation. Reviewers note potential safety concerns due to the presence of homeless populations and drug activity in the area, so exercise caution during your self-guided adventure.
Read our full review: Self Guided Solo “Weird and Wonderful Portland” Walking Tour in Old Town Review
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Portland Maine Self-Guided Walking Audio Tour
Enjoy the captivating history and charming sights of Portland, Maine, with this self-guided walking audio tour. Powered by the Action’s Tour Guide App, this tour offers engaging storytelling, a proven narrator, and the opportunity to dive deeper into any enjoyed story.
Equipped with offline maps and a comprehensive route, the tour ensures you won’t miss a beat. Simply download the app, follow the setup instructions, and embark on your journey at your own pace. Whether you’re a solo explorer or a couple sharing headphones, this flexible and convenient tour provides a memorable experience, complete with travel tips, narrated audio, and recommendations for additional activities.
Read our full review: Portland Maine Self-Guided Walking Audio Tour Review
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Self-Guided Driving & Walking Bundle of Portland Maine Tours
Why settle for just one way to explore the captivating city of Portland, Maine? The Self-Guided Driving & Walking Bundle of Portland Maine Tours offers the best of both worlds.
With this comprehensive package, you’ll enjoy engaging storytelling, a proven narrator, and a flexible route that allows you to see everything at your own pace. The offline capabilities, including maps and hands-free audio, ensure you won’t miss a beat, even without a signal.
And with a more affordable price tag than bus or guided tours, this bundle is a smart choice for budget-conscious travelers. Whether you prefer to walk or drive, this tour has you covered, making it the perfect way to discover the charm of Portland, Maine.
Read our full review: Self-Guided Driving & Walking Bundle of Portland Maine Tours Review
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Distillery Row of Portlands Eastside Walking Tour
Explore the vibrant Distillery Row on Portland’s Eastside with this walking tour. The tour takes you to two stops for coffee and/or tea tastings, offering a chance to discover the city’s thriving coffee culture.
Beginning at the ActivSpace building, you’ll have a maximum of 10 travelers in your group, ensuring an intimate experience. While the tour isn’t wheelchair accessible, it’s conveniently located near public transportation, making it accessible to most travelers.
Gratuities are welcomed, and you can book with the assurance of free cancellation up to 24 hours before the start. With a lowest price guarantee, this tour is a must-do for those seeking to enjoy Portland’s Eastside and its captivating coffee scene.
Read our full review: Distillery Row of Portlands Eastside Walking Tour Review
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Mississippi Avenue Walking Food Tour
Discover the vibrant flavors of Portland’s Mississippi District on this guided food tour. Explore a curated selection of 5-7 food carts, restaurants, bars, and tasting rooms, each offering a tantalizing taste of the local cuisine. Personalized recommendations from your knowledgeable guide will ensure you don’t miss a beat, whether you’re seeking the best dining, nightlife, or outdoor recreation.
With a maximum of 10 travelers and wheelchair accessibility, this tour caters to all. Conveniently located near public transportation, the 3-hour experience starts and ends at 3330 N Mississippi Ave. Boasting 100% traveler recommendation, this is a must-do for anyone seeking an authentic culinary adventure in Portland’s vibrant Mississippi Avenue neighborhood.
Read our full review: Mississippi Avenue Walking Food Tour Review
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Portlands Historic Heart: A Walking Tour of the City Center
Stepping away from the vibrant flavors of the Mississippi District, this walking tour immerses visitors in the historic heart of Portland. Led by a local professional guide, the tour begins at Director Park, where guests can admire the pavement checkerboard before setting out to explore the city’s landmarks.
Along the way, they’ll discover the iconic Pioneer Courthouse Square, a lively hub of activity. The tour culminates at this bustling destination, providing the perfect opportunity to continue exploring Portland’s rich history and charming urban landscape on one’s own. With free cancellation and flexible booking, this guided experience offers an insightful and convenient way to explore the city’s captivating past.
Read our full review: Portlands Historic Heart: A Walking Tour of the City Center Review
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The Sum Up
Portland’s vibrant walking tours offer a captivating way to take in the city’s culinary delights, historical landmarks, and local neighborhoods. Whether seeking a guided experience or a self-guided adventure, visitors can customize their exploration to uncover the city’s hidden gems and savor the unique flavors that make Portland a standout destination. With such a diverse range of options, there’s a walking tour to suit every interest and taste.