The 3 Best Walking Tours in Portland Maine
Portland, Maine, is a city full of surprises, with its lively Old Port, historic waterfront, and vibrant cultural scene. What makes exploring Portland on foot so appealing is the chance to truly connect with its local flavor—whether through tasting Maine’s best bites, uncovering stories most visitors miss, or learning about the city’s Black history. Walking tours in Portland offer a deep dive into its character, all while enjoying the fresh ocean air and charming streets.
Unlike bus tours or self-guided wandering, these guided walks provide insights you won’t find in guidebooks. Whether you’re after a delicious taste of Maine, a historical perspective, or meaningful stories of Black Portland, there’s a tour tailored to your interests. Booking early is wise—these popular experiences fill up fast, especially in peak season.
Quick Overview
Portland offers a variety of walking tours that cover food, history, and local culture. The Old Port Culinary Walking Tour highlights Maine’s food scene with tastings and stories from local artisans. The Hidden Histories Guided Walking Tour explores lesser-known stories behind Portland’s landmarks. And the Black History Guided Walking Tour takes you through the city’s Black communities and their impact over centuries. Read on for detailed breakdowns of each.
1. Portland: Old Port Culinary Walking Tour
This culinary walking tour offers a tasty way to explore Portland’s iconic Old Port district. For around $160 per person, you’ll spend about three hours sampling local Maine-inspired food and drinks while soaking in the historic streets. The tour is lauded, with a 4.8 out of 5 rating from over 100 reviews, and guides like AJ are praised for their knowledge, humor, and personable style.
What makes this tour stand out is its focus on local culinary artisans, where you’ll meet the chefs and brewers behind Portland’s best. You’ll taste Maine craft beer, learn how the city’s food scene evolved, and get insider tips for the rest of your trip. The tour balances history with food, giving you a sense of Portland’s foodie culture—from seafood and lobster rolls to artisanal cheeses and local beverages.
Guests often mention how fun and informative the experience is, even in less-than-perfect weather, thanks to the engaging guide and varied tastings. “AJ was a treat,” one review states, highlighting the personal touch. The only downside is the price, but it’s reflected in the quality of food and storytelling.
Bottom Line: If you love good food, local stories, and meeting Maine artisans, this tour delivers a memorable taste of Portland and a great way to orient yourself in the Old Port.
2. Portland, Maine: Hidden Histories Guided Walking Tour
For a deeper understanding of Portland’s lesser-known stories, this Hidden Histories Guided Walking Tour is a clever choice. Priced at just $49 per person and rated 4.9 out of 5 from over 60 reviews, it’s perfect for history buffs and curious travelers alike. It lasts about two hours and covers downtown, Old Port, and the working waterfront with a local public historian leading the way.
What sets this tour apart is its focus on stories of war, economic change, and pioneering women who shaped Portland. You’ll get to smell the ocean air at the waterfront, see buildings that survived the 1866 fire, and learn about Indigenous Wabanaki diplomats and Chinese laundrymen—stories often omitted from standard guides. The itinerary includes stops at Post Office Park, Commercial Street, and Bell Buoy Park.
Tour participants rave about how engaging and thorough the guide is. “It’s a fantastic way to see Portland beyond the usual sights,” one reviewer says, emphasizing the tour’s storytelling and local perspective. It’s well-suited for travelers who enjoy history that feels personal and authentic.
Bottom Line: For those interested in Portland’s economic, social, and cultural nuances, this tour offers a vivid window into the city’s hidden past.
3. Portland, Maine: Black History Guided Walking Tour
Walking through Portland with this Black History Guided Tour gives you a rare insight into the city’s Black community’s contributions over 400 years. At $49 per person, this two-hour tour is rated 4.9 out of 5 from a small but dedicated group of reviewers. Led by a passionate public historian, it traces stories from 1604 to today, starting at First Parish and moving through the Old Port and Munjoy Hill.
What makes this tour distinctive is its focus on Black explorers, mariners, political leaders, and families who ran the Underground Railroad. You’ll visit homes, see buildings associated with Black self-determination, and learn how Portland’s Black residents influenced the city’s growth. The tour emphasizes personal stories that highlight resilience and leadership, making it a powerful experience.
Reviews praise the guide’s knowledge and enthusiasm—“genuine excitement and passion,” says one. It’s ideal for travelers interested in social history and civil rights or those wanting to understand Portland’s diversity. The tour’s intimate size and storytelling make it memorable.
Bottom Line: If you’re interested in Portland’s Black heritage and its ongoing impact, this tour provides a meaningful and eye-opening perspective.
How to Choose
When deciding between these walks, consider your interests and schedule. If your priority is tasting Portland’s famous food scene and meeting local chefs, the Old Port Culinary Walking Tour is an excellent pick. It’s perfect for foodies, those wanting a relaxed, social experience, or anyone wanting a comprehensive introduction to Portland’s gastronomic culture.
For those curious about Portland’s quiet stories—the buildings left standing after fires, the influence of Indigenous and immigrant communities—the Hidden Histories Tour offers a richer context that complements a standard sightseeing itinerary.
Finally, if you have a special interest in Black history and civil rights, the Black History Tour is a compelling way to gain new insight into Portland’s diverse roots.
All tours require some walking and are generally suited for active travelers. Book in advance, especially during peak summer months, since these popular experiences fill quickly.
Final Thoughts
Portland Maine’s walking tours cover a broad spectrum—from culinary delights to powerful stories of resilience and hidden histories. For a lively, food-focused introduction, the Old Port Culinary Tour is hard to beat. Those wanting to go beyond the surface will appreciate the Hidden Histories Tour, while history enthusiasts interested in Portland’s Black communities should not miss the Black History Tour.
Choosing the right tour depends on what stories excite you most. Whichever you select, early booking is a smart move to ensure a spot. Portland’s stories are waiting to be uncovered—step out and explore with confidence.