Portland’s historic waterfront district offers several excellent walking tours worth your time and money.
The Old Port Brewery & Pub tour hits the city’s top craft beer spots, while food lovers shouldn’t miss the Old Port Culinary tour – both provide generous samples and well-researched historical commentary.
History buffs will appreciate the Hidden Histories and Black History tours, which uncover fascinating stories often overlooked in guidebooks.
For independent travelers, the Self-Guided Walking & Driving Audio Tour Bundle provides good value and flexibility.
Let’s look at our favorite Portland walking tours in detail.
Top Tours
- The Old Port Brewery & Pub Walking Tour offers a 2.5-hour exploration of local craft breweries and pubs with complimentary tastings and pub snacks.
- The Old Port Culinary Walking Tour provides a 2-hour culinary adventure featuring locally-sourced ingredients and Maine-made craft beers.
- The Hidden Histories Guided Walking Tour covers significant historical narratives in downtown Portland, including Indigenous Wabanaki diplomats and female figures.
- The Black History Guided Walking Tour highlights Portland’s Black heritage, from 1604 to the present, with interactive experiences and stories of Black stevedores and Underground Railroad participants.
- The Self-Guided Walking & Driving Audio Tour Bundle offers a comprehensive 75-minute audio guide for exploring Maine’s landscapes and historic sites at your own pace.
Portland, Maine: Old Port Brewery & Pub Walking Tour
Exploring Portland’s vibrant Old Port district, you’ll embark on a captivating 2.5-hour walking tour that delves into the city’s thriving craft beer scene.
With free cancellation up to 24 hours in advance, you can book this tour with flexibility. The experience includes visits to top local craft breweries and pubs, where you’ll gain insight into Portland’s beer history from knowledgeable guides.
Savor a complimentary pub snack and beer tastings, as you explore a selection of brews from over 30 Maine breweries. Key stops include Liquid Riot and Shipyard Brewing Company, culminating in a tasting at the Portland Beer Hub, where you’ll receive a 10% discount on additional purchases.
With an overall rating of 4.8 out of 5, this tour is praised for its informative and engaging nature, as well as the quality of the local guides and beer selections.
Read our full review: Portland, Maine: Old Port Brewery & Pub Walking Tour Review
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Portland: Old Port Culinary Walking Tour
On this 2-hour culinary walking tour of Portland’s vibrant Old Port district, you’ll indulge in a delectable exploration of the city’s thriving food scene.
Rated 4.8 out of 5 stars with 12 reviews, this $89 tour promises to whet your appetite with a behind-the-scenes look at local eateries, breweries, and artisanal producers.
Led by knowledgeable guides, you’ll stroll through the historic cobblestone streets, stopping to sample locally-sourced ingredients and learn about the city’s rich culinary heritage.
Indulge in Maine-made craft beers, savor fresh-caught seafood, and discover the stories behind the ingredients that make Portland’s cuisine so unique.
Whether you’re a foodie or simply looking to experience the flavors of the city, this Old Port Culinary Walking Tour offers a delicious way to learn about Portland’s vibrant culture.
With small group sizes, free cancellation, and an average rating of 4.8 stars, this tour is a must-do for any visitor seeking to uncover the epicurean delights of Maine’s largest city.
Read our full review: Portland: Old Port Culinary Walking Tour Review
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Portland, Maine: Hidden Histories Guided Walking Tour
Enjoy Portland’s captivating past on this 2-hour Hidden Histories Guided Walking Tour. You’ll enjoy free cancellation up to 24 hours in advance and flexible travel plans without any upfront payment.
Led by Dugan Murphy, Maine’s #1 tour guide, this small-group experience provides unique insights beyond the typical tourist attractions.
You’ll explore the Old Port, downtown, and waterfront, learning about historical influences from war, nature, and economics. Discover stories of Indigenous Wabanaki diplomats and Chinese laundrymen, and recognize the contributions of female figures along Maine’s coast.
Along the way, you’ll take in fresh ocean air, view buildings that emerged after the great fire of 1866, and stroll past brick sidewalks and Victorian-era architecture.
The tour’s engaging storytelling, personalized attention, and local expertise create an unforgettable experience. Bring comfortable shoes, an umbrella, and weather-appropriate clothing, as you navigate the 1.5-mile route, including some uphill sections and stairs.
A portion of ticket sales supports the restoration of the Abyssinian Meeting House.
Read our full review: Portland, Maine: Hidden Histories Guided Walking Tour Review
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Portland, Maine: Black History Guided Walking Tour
Delving into Portland’s rich Black heritage, this captivating 2-hour walking tour invites you to uncover the impactful contributions of the city’s African American community.
Led by a knowledgeable English-fluent guide, you’ll explore Maine’s Black history from 1604 to the present, discovering the stories of Black stevedores, Yankees, and Underground Railroad participants.
Strolling through Portland’s Old Port and working waterfront, you’ll encounter monuments and institutions reflecting Black economic and political power.
The tour’s small group size of 15 or fewer ensures an engaging, interactive experience, allowing you to ask questions and gain deeper insights.
With no upfront payment required and free cancellation available up to 24 hours in advance, this tour offers flexibility and convenience.
Dress comfortably, wear appropriate shoes, and be prepared for weather changes as you embark on this enlightening journey through Portland’s Black history.
Read our full review: Portland, Maine: Black History Guided Walking Tour Review
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Maine: Self-Guided Walking & Driving Audio Tour Bundle
Set out on a self-guided journey through the captivating landscapes and historic sites of Maine with this comprehensive walking and driving audio tour bundle.
Explore the charming coastal towns and discover the rich maritime heritage at your own pace. The 75-minute audio guide provides a seamless, immersive experience, narrating the stories behind famous lighthouses, quaint fishing villages, and hidden gems.
Whether you prefer to stroll or drive, this bundle offers the ultimate flexibility. Venture out on foot and uncover the hidden histories of the region, or hop in your car and witness the stunning Maine coastline from the comfort of your vehicle.
With a user-friendly mobile app, you’ll have the tour at your fingertips, allowing you to pause, rewind, and revisit your favorite moments.
Priced at just $6.75, this self-guided adventure is an affordable and enriching way to explore the natural wonders and cultural heritage of Maine.
Embark on your journey and discover the true essence of this captivating destination.
Read our full review: Maine: Self-Guided Walking & Driving Audio Tour Bundle Review
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Common Questions
What Is the Best Time of Year to Take These Walking Tours?
The best time of year for walking tours is typically when the weather is mild and pleasant. Spring and fall tend to offer the most comfortable conditions for exploring on foot, with fewer crowds and milder temperatures than the peak summer months.
Are the Walking Tours Accessible for People With Disabilities?
The walking tours are generally accessible for people with disabilities. Most offer accommodations like wheelchair-friendly routes, audio guides, and staff assistance. Check with the tour operators to ensure the specific tour meets your needs.
Do the Tours Include Any Food or Beverage Tastings?
Many walking tours in Portland, Maine include food or beverage tastings. You’ll get to sample local specialties and learn about the city’s culinary scene. Check tour descriptions to see if tastings are included in the itinerary.
How Long Do the Walking Tours Typically Last?
The walking tours typically last 2-3 hours, allowing you to explore the city’s highlights at a leisurely pace. Many offer stops for local food and beverage tastings to complement the historical and cultural insights.
Are There Any Discounts or Packages Available for the Walking Tours?
Many walking tour companies in Portland, Maine offer discounts and package deals. You can often find reduced rates for seniors, students, or if you book multiple tours. Check the tour operators’ websites for current specials and bundle options.
Sum Up
Discover Portland’s rich history, vibrant culinary scene, and hidden gems through these engaging walking tours. From exploring the Old Port’s breweries to uncovering the city’s Black heritage, these guided experiences offer an immersive way to explore the best of what Maine’s largest city has to offer. Whether you choose a curated tour or a self-guided adventure, you’ll leave with a deeper appreciation for this coastal gem.