Portland is a city that loves to walk. Its compact downtown, lively neighborhoods, and eclectic vibe make exploring on foot a real pleasure. Whether you’re craving a foodie adventure, eager to uncover hidden histories, or interested in local spirits and brews, Portland offers a walking tour for every taste. We especially like the Portland Delicious Donut Adventure for its sweet treats and insider spots, and the A Walk Through Time Tour for a fascinating look at Portland’s past. Both tours give you a chance to stretch your legs while soaking in local culture and stories. For a spooky twist, the Walk With Ghosts in Portland offers a chilling look at the city’s haunted side. Each of these experiences highlights Portland’s charm—on foot, it’s hard to beat.
Quick Overview
Portland’s walking tours range from culinary explorations and historical walks to ghost stories and breweries. You can indulge in Portland’s famous donuts, explore its centuries-old architecture, or learn about its diverse communities. The list includes experiences like Portland Delicious Donut Adventure, A Walk Through Time, and Ghost Tours. Whatever your interest, you’ll find a well-priced, engaging tour that fits your schedule and energy level.
1. Portland Delicious Donut Adventure & Walking Food Tour
This tour captures Portland’s sweet tooth with visits to iconic spots like Voodoo Donuts and lesser-known local favorites. It includes tastings at every stop, and your guide will share the story behind Portland’s donut obsession. Expect a 2-hour walk through downtown with stops at Sesame Donuts, Coco Donuts & Coffee, and a quick photo at the Portlandia statue. Guests rave about the guide’s personality and the delicious variety—”The raspberry donut at the mini shop is a must-try,” says one review. With vegan and gluten-free options, it’s inclusive for most dietary needs. This tour is perfect for sweet tooths and dessert lovers wanting a fun, relaxed pace while exploring Portland’s core.
Bottom Line: Great for those who want to indulge and learn about Portland’s donut culture in a lively, friendly atmosphere.
2. A Walk Through Time Tour in Portland
At number 2, this 2-hour historical walk offers a deep dive into Portland’s past. You’ll visit key sites like Lobsterman Park, the Old Port, and the Eastern Cemetery, hearing stories about influential figures like Henry Wadsworth Longfellow and Portland’s maritime history. The guide brings history alive with fascinating tales about architecture, local industry, and notable residents. The tour caps at 20 people, making it intimate and ideal for history buffs or curious travelers. Guests mention Tyler’s engaging storytelling and how the tour provided a perfect ending to their Portland visit. It’s a balanced mix of architecture, local lore, and city views, offering good value at $48.99.
Bottom Line: A highly recommended choice for travelers wanting a comprehensive, engaging overview of Portland’s history on foot.
3. Portland, Maine: Hidden Histories Guided Walking Tour
This small-group tour, lasting about 2 hours, takes you beyond the usual tourist spots. You’ll wander through downtown and the Old Port, discovering hidden landmarks and stories of Wabanaki leaders, underrepresented communities, and forgotten heroes. Your guide, Dugan, focuses on under-told stories, including the resilience of Indigenous peoples and the lives of historically marginalized figures. Guests praise Dugan’s “wild facts and lively storytelling”, making history engaging for all ages. The tour is perfect for those interested in social history and local culture, and the small-group format ensures personalized attention.
Bottom Line: Best suited for travelers who want to see Portland from a different perspective, exploring its lesser-known stories.
4. Old Port Culinary Walking Tour from Portland
For around $159, the Old Port Culinary Walking Tour dives into Portland’s culinary scene with stops at five to six eateries. You’ll sample Maine-inspired dishes—from lobster rolls to local desserts—and learn about Portland’s food history along the way. The tour lasts 2 to 3 hours and offers enough tastings to replace a meal. Guests love the charisma of guides like AJ, and rave about the generous portions and local insights. It’s best for food lovers who want an immersive experience and don’t mind walking a bit between stops. The limited group size makes it intimate, with a focus on authentic flavors.
Bottom Line: Ideal for those seeking a gourmet experience paired with local storytelling.
5. Intro to Portland Small Group Walking Tour
Starting at just $29, this introductory tour covers Portland’s highlights in about 2 to 2.5 hours. Meeting in Director Park, you’ll stroll through South Park Blocks, learn about city architecture, and hear stories about Portland’s unique neighborhoods. Guides like Shannon and Kelly are praised for their friendly, informative style, making it perfect for first-timers or those pressed for time. The small group ensures personalized attention, and the flexible start times help fit busy schedules. Guests value the manageable pace and insightful commentary. It’s a solid budget-friendly option that still offers plenty of local flavor.
Bottom Line: A great choice for travelers wanting a quick, friendly introduction to Portland.
6. Portland Walking Food Tour With Secret Food Tours
At number 6, this 3.5-hour food and culture tour combines Portland’s best bites with engaging stories. You’ll visit up to seven eateries, sampling everything from fried sausages, ramen, donuts, to secret dishes. The route takes you through Portland’s coolest neighborhoods, with visits to Portland’s eclectic food scene and landmarks. Guides offer insights into Portland’s culinary evolution, and the generous tastings are enough for lunch. Reviewers appreciate the knowledgeable guide Honey and the chance to explore local favorites beyond tourist spots. It’s perfect for foodies seeking a full stomach and a local perspective.
Bottom Line: Best for those who want a full cultural and culinary immersion in Portland.
7. Portland, Maine: Black History Guided Walking Tour
This 2-hour tour provides a focused look at Black history in Portland, emphasizing figures like Frederick Douglass and the Abyssinian Meeting House. Led by guide Dugan, it explores Portland’s East End, uncovering stories of resistance, resilience, and community achievements. The tour is capped at 15 people, allowing for deep discussion. Guests mention how the guide’s passion and knowledge made history come alive, especially highlighting underrepresented narratives. It’s suited for travelers interested in social justice, cultural diversity, and local activism.
Bottom Line: A powerful, thoughtful walk for those interested in under-told stories and historic figures shaping Portland.
8. Old Port “Seafood Lovers” Walking Lunch Tour in Portland
This seafood-focused tour offers a tasty 2.5-hour walk along Portland’s waterfront, with stops for lobster rolls, chowder, and craft beer. You’ll learn about Maine’s famous seafood industry and how it influences Portland’s culture. With delicious tastings included—enough for lunch—and a souvenir gift for each participant, it’s perfect for seafood fans. Guides like AJ make the experience lively and informative, with reviews praising the fresh, local flavors and engaging stories about lobster fishing. It’s best suited for seafood lovers who want a relaxed, flavorful outing.
Bottom Line: Great for those wanting to savor Maine’s seafood while exploring Portland’s waterfront.
9. Portland’s Best Chocolate and Coffee Walking Tour
This 2.5-hour tour combines Portland’s coffee and chocolate scenes with visits to Azar Indulgences and local coffee shops. The route covers about 2 miles, with tastings of Belgian chocolates, locally roasted coffee, and wine paired chocolates. Guests rave about guides like Nancy, who share knowledge about the craft of chocolate and coffee, making it a delightful sensory experience. It’s perfect for sweet-tooths and caffeine enthusiasts who want a relaxed pace and engaging stories. The small group size ensures personal attention and a chance to learn as you go.
Bottom Line: An indulgent, flavorful way to discover Portland’s artisan chocolate and coffee culture.
10. Mississippi Avenue Walking Food Tour
This 3-hour tour explores Portland’s Mississippi District, known for live music, eclectic shops, and excellent restaurants. You’ll sample egg sandwiches, donuts, gourmet salts, and Cuban cuisine at local favorites. The guide, Danny, shares stories about the neighborhood’s culture and food scene. Reviewers mention how the tour offers delicious bites and local insights, making it a rewarding experience for food lovers. The tour is best for those wanting to combine food with neighborhood exploration.
Bottom Line: A relaxed, tasty way to see a lively Portland neighborhood.
11. Portland Pubs Walking Beer Tour
For lovers of craft beer, this 2.5-hour tour visits three local breweries, including Shipyard Brewing and Liquid Riot. You’ll learn about beer production, sample about a dozen beers, and enjoy snacks along the way. Reviewers highlight the knowledgeable guides like Pete, and the chance to explore Portland’s beer scene beyond the bars. It’s well-suited for beer aficionados who want a behind-the-scenes look and a social outing. The included minibus transit makes it easy to focus on the tastings and conversation.
Bottom Line: Perfect for those looking to explore Portland’s brewery culture with a relaxed, guided experience.
12. Walk With Ghosts in Portland
This 1-hour tour offers a quick, spooky peek into Portland’s haunted past. You’ll explore monument square and historic neighborhoods, hearing tales of ghosts, spooky legends, and spectral sightings. The guide shares stories of civil war spirits, haunted buildings, and local legends that will send shivers down your spine. Guests mention how knowledgeable and entertaining guide Hannah was, making it a fun, eerie experience. It’s ideal for families or those interested in supernatural stories.
Bottom Line: An entertaining, ghostly walk for a short but memorable ghost-hunting adventure.
13. Makers and Artisans of Portland Walking Tour
This 2-hour 15-minute tour explores Portland’s East Side, visiting local breweries, tea makers, and art shops. You’ll visit Cargo, Steven Smith Teamaker, and Cova Coffee—sampling teas, beers, and artisanal coffees. The guide’s passion for local craftsmanship shines through, and guests appreciate the small group format for personalized attention. It’s suited for culture and craft lovers with an interest in Portland’s creative industries.
Bottom Line: A detailed, taste-rich tour focusing on Portland’s artisan scene and innovative producers.
14. True Crime in Portland’s Old Port – Evening Walking Tour
This 2-hour exploration uncovers Portland’s darker side, from mobsters to bootleggers. Walking through the Old Port at night, you’ll hear stories of scandals, criminal enterprises, and notorious figures who shaped the city’s underbelly. The guide weaves true crime tales with the city’s architecture, creating a compelling contrast. The tour appeals to crime history fans and those wanting a thrilling, different perspective on Portland’s past.
Bottom Line: A fun, slightly edgy tour suited for adventure seekers interested in the city’s less-glamorous stories.
15. Macabre Ghost History of Portland, Oregon walking tour
Over 1.5 miles, this tour blends ghost stories with historic sites, including cemeteries and old buildings. You’ll learn about fire deaths, watery graves, and spirits believed to haunt Portland. The guide shares verifiable stories of specters and eerie events. Guests note the informative nature of the tour, even if some expected more ghostly encounters. It’s ideal for ghost enthusiasts who enjoy history and supernatural tales in equal measure.
Bottom Line: A solid choice for ghost story enthusiasts wanting history with a spectral twist.
16. 2-Hour Portland Old Port Ghost Walking Tour
This shorter, 2-hour ghost walk takes you through Portland’s waterfront at night, with tales of sea serpents, haunted restaurants, and spectral pirates. The tour features stops at places like DiMillo’s and Custom House Wharf, where paranormal activity is rumored. Guests enjoy the interactive storytelling and ambiance. It’s perfect if you want a quick, spooky experience without committing to a longer tour.
Bottom Line: Ideal for ghost lovers seeking a short, fun haunted walk in Portland.
How to Choose
When selecting a walking tour in Portland, think about your specific interests. Are you a food enthusiast? The Old Port Culinary Tour offers an indulgent taste of Maine’s best eateries. Want to learn about local history? The A Walk Through Time provides a comprehensive story of the city’s development. For ghost stories or true crime, the tours focusing on haunted sites or Portland’s criminal past will satisfy your curiosity. Budget, duration, and group size are also key considerations. For instance, the Intro to Portland is perfect for a quick, affordable overview, while the Seafood Lovers Tour is ideal for a relaxed, culinary-focused experience. Booking early is recommended, especially in peak seasons, to secure your spot.
Final Thoughts
Portland’s walking tours showcase its culinary delights, rich history, and haunted legends. Whether you’re after a sweet treat, a cultural deep dive, or spooky stories, there’s an experience that will match your curiosity. For a fun, taste-filled day, the Donut Tour hits the mark. For history lovers, the Time Tour offers a thorough look at Portland’s story. And if you’re in the mood for something spooky, the Ghost Walk delivers a fun, chilling adventure. No matter what, booking early will help you secure your spot on these popular walking tours.