Portland, Maine, is a city that invites exploration on foot. Its compact size, charming cobblestone streets, and waterfront views make it perfect for walking tours that reveal the city’s hidden stories and local flavors. We especially love the Portland: Old Port Culinary Walking Tour for its delicious tastings and engaging local food scene, as well as the Hidden Histories Guided Walking Tour for uncovering lesser-known tales of the city’s past. Portland’s walkable layout and friendly neighborhoods make these tours not only easy to enjoy but packed with authentic experiences. Whether you’re after a food adventure, a dive into history, or a spooky ghost story, Portland’s diverse options have you covered.
Quick Overview
Our list includes a variety of walking tours, from food-focused outings and craft beer explorations to deep dives into Portland’s Black history and ghost stories. Some tours highlight local cuisine, like the Walking Food Tour – Warm Donuts & History, while others reveal Portland’s rich past, such as the Black History Guided Walking Tour. For thrill-seekers, the Ghost Walk offers a supernatural look at the city’s Victorian-era architecture. And if craft beer or coffee interest you, there are dedicated brewery and coffee tours. Below, we explore each experience in detail to help you decide which best fits your Portland adventure.
1. Portland: Old Port Culinary Walking Tour
At number 1 on our list, the Portland: Old Port Culinary Walking Tour is a true highlight for food lovers. For $160 per person, you’ll spend 2.5 hours strolling the historic streets of Portland’s Old Port, indulging in local Maine-inspired foods. This tour doesn’t just satisfy your taste buds; it offers an engaging look into the city’s culinary history and introduces you to local artisans who share how they started their businesses. You’ll sample different dishes, learn about Portland’s seafood heritage, and even taste and take home iconic Maine craft beer.
What makes this tour special is the combination of delicious food, local stories, and meet-and-greet moments with artisans. The relaxed pace allows guests to savor each bite while soaking in the charming atmosphere of cobblestone streets and historic buildings. The guide’s stories bring Portland’s food scene to life, making it ideal for anyone wanting a flavorful, informative experience. The reviews reflect high satisfaction, with a 4.8/5 rating based on 118 reviews, emphasizing the quality of the food and the knowledgeable hosts.
Bottom Line: This tour is perfect for foodies and those keen to explore Portland’s culinary scene while learning about its history. It offers a rich taste of Maine’s flavors in a friendly, relaxed setting.
2. Portland, Maine: Hidden Histories Guided Walking Tour
Next up, the Hidden Histories Guided Walking Tour is a 2-hour journey through Portland’s lesser-known stories. For just $49, you’ll explore downtown, Old Port, and the working waterfront with a public historian who sheds light on events and figures often left out of textbooks. Walking along the waterfront, you’ll breathe in the ocean air while discovering stories of Indigenous Wabanaki diplomats, Chinese laundrymen, and the forces of war and economic change that shaped Portland.
What sets this tour apart is its focus on diverse perspectives and small-group intimacy, enhancing the storytelling experience. You’ll see historic buildings that survived Portland’s 1866 fire and learn how economic forces influenced the city’s development. The guide’s passion and depth make this tour both educational and engaging, appealing to history buffs and curious travelers alike.
Bottom Line: If you want to see Portland through a different lens and uncover stories often overlooked, this tour offers a meaningful, well-rounded perspective on the city’s past.
3. Portland, Maine: Black History Guided Walking Tour
The Black History Guided Walking Tour offers a 2-hour exploration of over 400 years of Black influence in Portland. For $49, you’ll follow a public historian through the Old Port and East End, uncovering stories of Black explorers, mariners, religious leaders, and politicians. The tour highlights Black Yankees’ political leadership and self-determination, as well as homes that played a role in the Underground Railroad.
What makes this tour stand out is its focus on Maine’s Black heritage, a narrative often underrepresented in other city tours. During the walk, you’ll learn about Black families who ran businesses and helped shape Portland’s social fabric. The small group setting allows for more personal storytelling, and the reviews commend the guide’s depth of knowledge.
Bottom Line: This tour is an excellent choice for those interested in African American history, civil rights, and Portland’s diverse cultural roots.
4. Portland: Walking Food Tour – Warm Donuts & History
For a sweet twist, the Walking Food Tour – Warm Donuts & History combines Portland’s legendary donuts with its historic sites. At $57 for 1.5 hours, this tour is shorter but packed with flavor — you’ll visit 3 top donut shops and sample a total of 6 donuts, skipping queues at popular spots. Along the way, the guide shares stories of Portland’s history, landmarks like Monument Square, and the working waterfront, making the experience both tasty and educational.
Guests rave about the variety and quality of donuts, and the tour’s lively pace keeps things fun. The guide’s legend of Portland’s “fried dough creation” adds local color. It’s a great pick if you want to combine a snack-focused adventure with sightseeing.
Bottom Line: Ideal for sweet tooths and those wanting a quick, flavorful taste of Portland’s culinary and historic charm.
5. Portland, Maine: Old Port Brewery & Pub Walking Tour
The Old Port Brewery & Pub Walking Tour offers a 2.5-hour stroll through Portland’s craft beer scene for $99. You’ll visit three local breweries and pubs, tasting Portland’s best brews while learning about the city’s beer history, which dates back over a century. The tour includes a pub snack, making it a well-rounded experience for beer enthusiasts.
The guide’s storytelling about Portland’s brewing evolution is engaging, and guests particularly enjoy the small group atmosphere and the chance to sample different styles of Maine craft beer. The tour is perfect for those who want to combine history, local drinks, and a relaxed walk — a good value considering the three tastings and insight provided.
Bottom Line: This tour suits craft beer lovers and anyone curious about Portland’s brewing legacy, combining education with delicious samples.
6. Portland: Ghost Walk
For those intrigued by the supernatural, the Portland Ghost Walk is a 1-hour journey into the city’s haunted past. Priced at $30, it explores the cobblestone streets and Victorian neighborhoods in search of spirits lingering from Portland’s history. The tour hints at what lurks beneath the streets and examines Victorian-era architecture reputed to be haunted.
This tour is ideal for night owls or anyone interested in ghost stories and local legends. It’s a shorter, immersive experience that appeals to those seeking a different kind of adventure. While only two reviews are available, the stories and atmospheric setting make it a fun, spooky addition to any Portland itinerary.
Bottom Line: Best suited for ghost enthusiasts or those looking for a spooky evening walk with a historical twist.
7. Portland: Donut and Craft Drink Walking Tour
At $74, the Donut and Craft Drink Walking Tour offers a sweet and spirited 2-hour journey through Portland’s local scene. You’ll savor artisan donuts and sample local beers, ciders, cocktails, or mocktails. Starting and ending at the Maine Souvenir Shop, the tour combines tasting, storytelling, and scenic city strolling.
Guests enjoy learning about Portland’s “Inferno Years” and the evolution of its donut culture, alongside tasting pours from select local breweries and bars. The tour’s lively pace and diverse offerings make it a hit for those wanting a mix of culinary delights and local lore.
Bottom Line: Perfect for those who want a relaxed, tasty exploration of Portland’s creative food and drink scene, with a fun storytelling element.
$74 per person
8. Portland: Eastside Coffee Roasters Walking Tour
Finally, for caffeine aficionados, the Eastside Coffee Roasters Walking Tour combines Portland’s vibrant neighborhood with coffee culture. For $55, you’ll walk 1.5-3 miles, sampling coffee at two local roasters and learning about their unique brewing methods and the neighborhood’s history.
This tour is great for travelers who want to explore Portland’s creative scene beyond food and beer, focusing on artisanship and community. Reviews are limited but positive, emphasizing the intimate experience and quality coffee tastings.
Bottom Line: Ideal for coffee lovers and those interested in Portland’s artisan scene, offering a relaxed walk with a caffeinated reward.
$55 per person
How to Choose the Perfect Walking Tour in Portland
When selecting a tour, consider your interests and how much time you want to spend. If food is your main goal, the culinary Old Port Food Tour and Donut & Craft Drink Tour are excellent options. For a deeper dive into Portland’s stories, the Hidden Histories and Black History tours offer meaningful insights. Interested in the spooky side? The Ghost Walk provides a quick, atmospheric adventure.
Budget and time also matter. Tours like the ghost walk or donut tour are shorter and less expensive, ideal for a quick taste, while the culinary and brewery tours provide more immersive experiences at a higher price point. Booking early, especially in peak tourist season, ensures you secure a spot on your preferred tour.
In summary, Portland Maine offers a diverse array of walking experiences, ranging from food and drink explorations to historical and spooky tales. For a comprehensive taste of what the city has to offer, the Old Port Culinary Tour and Hidden Histories are highly recommended. Whether you’re a foodie, history lover, or thrill-seeker, there’s a Portland walking tour that will enrich your visit and leave you wanting to come back for more. Book early, and enjoy stepping into Portland’s stories and flavors.