The Best Walking Tours Around Portland, Maine

Visiting a new city can be an exciting adventure. Learning about historic landmarks, visiting museums, discovering unique architecture, trying new foods, and learning about local culture… It’s what traveling is all about! If you want to get a feel for the heartbeat and rhythm of a city, the best thing to do is get out there and explore. There is no better way to do this than on foot. You really get a feel for the sights, sounds, and even the smells that give a city its character and life.

Anyone can get online and look up where to eat or purchase some local goods, but it’s the hidden nooks that really define the soul of a city. Next time you visit Portland, don’t just discover what’s on the surface with basic sightseeing on the beaten path. Really dig in and explore one of the greatest cities in the United States. No matter your interests or budget there is a walking tour that is perfect for you in this classic New England town.

Maine Foodie Tours


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Don't just go out to eat, instead make it a dining experience! Maine Foodie Tours will satisfy even the most discerning of dining aficionados. Offering a variety of tours - most, of course, centered around food and drink - Maine Foodie Tours is a one-stop shop with pricing for every budget, and a theme for every taste, designed around Director Pamela Laskey’s admiration and passion for Maine’s unique culinary culture.

Experience some of the finest cuisine and cocktails Portland has to offer at dozens of award-winning restaurants. You'll want to check out their flagship tour, the Old Port Culinary Walking Tour. This is a leisurely paced 2.5 to 3 hour tour, taking you through the historic Old Port, feeding your senses as well as your hunger. For the beer enthusiast, there is no shortage of microbreweries sure to satiate every palate. Although “foodie” is right in the name, Maine Foodie Tours offers a variety of tours including happy hour tours, Doggy & Me Tours, boat tours, and historic tours.

Not all tours run year-round. Make sure to check availability.

Price: $49 - $200

Portland Freedom Trail


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History buffs will love to take a step back in time with this self-guided walking tour of thirteen Underground Railroad historic landmarks located throughout the city. Experience Portland from a different perspective as you walk in the footsteps of thousands of men, women, and children escaping the bonds of slavery. The Portland Freedom Trail is part of the larger network of Maine Freedom Trails, and it is administered by the Portland Freedom Trail Advisory Board.

Download the free guide:

Price: Free

Wicked Walking Tours


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If you’re looking to experience Portland in a truly spooktacular way, you do not want to miss out on the award-winning Wicked Walking Tour. This half-mile walking tour in the Old Port District is filled with ghosts, witch trials, pirates, and much more. The short distance and light-hearted nature of the tour makes it perfect for everyone from ages 8 to 80. Local professional actors and comedians take you on a tour through Maine’s dark history. Tours last about 75 minutes, and are sure to be an exciting and entertaining experience for all.

Tours do not run every night, so make sure to check availability.

Price: $14.99 - $19.99

Historic Workouts

Photo Credit: Historic Workouts via Facebook

Add a total body workout to your sightseeing experience as you tour Portland’s Old Port District with a certified fitness professional! Historic Workouts offers an array of fitness-focused tours that are suitable for a range of abilities. Choose the 90-minute Old Port Historic Workout for a more challenging experience, speed walking/light jogging to area landmarks where you’ll discuss their significance in Portland’s history over structured exercise routines. For a milder experience, consider the two-hour walking tour. Historic Workouts also hosts special holiday tours for Valentine’s Day, St. Patrick’s Day, 4th of July, and the winter holidays.

Tours are available seasonally. Year-round options available for private tours.

Price: Starting at $20

Wine Wise Wine & Food Walks


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Join Sommelier Erica Archer for a guided tour of Portland’s bustling restaurant scene, and enjoy food and wine pairings at four stops along the way. These highly-rated, intimate tours take place every Friday and Saturday, year-round. Wine Walks last just over two hours, and are typically themed around the traditions and flavors of various regions like France, Spain, and Italy. Additional options include the Spirits & Cocktail Walks every Sunday afternoon, and Wine & Oysters Walks on the last Sunday of each month.

Wine Wise also offers seasonal wine sails on board the immaculate Frances, a 74' Windjammer.

Price: Starting at $65

Portland Maine Walking Tours


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There’s nothing like local insight, and you’ll find plenty of that when you tour Portland with Jeff and Pete Lyons, two longtime Mainers with a passion for Portland. You’ll discover the area’s most unique offerings in art, architecture, history, food and drink, museums, music venues, and more while enjoying the company of knowledgeable locals who fast become friends. Choose from a two-hour tour of the Old Port District and waterfront, the three-and-a-half hour Portland On Tap tour of breweries and wineries, or the one-hour Heart of Portland tour.

All tours are available year-round and can be customized to your interests.

Price: Starting at $10

Beaten Path Tours


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Seasonal tours by reservation only, departing twice daily from June 15th to November 30th, with weekend tours available during the months of April, May, and November. These guided walking tours last just under three hours. Originating from the Old Port, the tour covers the history, architecture, museums, activities and nightlife that put Portland on the map. Walk the cobblestone streets of historic Portland as you explore the city’s coastline and the award-winning shops, restaurants, and pubs of the Old Port.

Price: Adults $20; Seniors and Military $17; Children under 12 FREE

In The Know Shopping Tours


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Find your Portland style with the help of fashion-forward locals! Join grandmother/ granddaughter team Alicia and Elisabeth on this unique, personalized walking tour focused on original New England fashion from locally-owned boutiques. Many of the stores offer discounts only available to tour participants.

Tours last anywhere from two to four hours, and a one-hour “sample tour” is also available.

Price: Starting at $45

Portland’s First Friday Art Walk

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Portland’s First Friday Art Walk is largest free monthly cultural event in Maine. This self-guided tour, hosted by Creative Portland, plots a path through the galleries, museums, alternative venues, and streets of Portland’s artistic epicenter - the colorful downtown district. This is a wonderful way to dig into the creative pulse of Maine culture while getting up close and personal with the artists and fellow art lovers. The Portland First Friday Art Walk takes place between 5PM and 8PM. Check out the Art Walk map to preview more than 100 stops along the route!

Price: Free

Greater Portland Landmarks Self-Guided Walking Tours

Photo Credit: Greater Portland Weekly Walking Group via Facebook

Discover Portland on your own terms with a self-guided tour. While a guided tour does offer some unique benefits, there is something to be said for getting out there and exploring your surroundings on your own terms. A self-guided tour gives you the ability to set your own pace and spend a little extra time in areas that really pique your interest. You can learn about Portland's rich and storied history and unique architecture while walking the cobblestone streets with a choice of four self-guided walking tours. Perfect for families and kids ages 8 and up.

Price: Starting at $7.95



Portland is one of the largest cities in New England and your options for entertainment, fun, food, and education are limitless. Get lost in a world of adventure on the cobblestone streets while learning about history, feeding your imagination in the Arts District and your appetite in the award-winning restaurants. Portland is a city bursting with culture and history and is famous for its local cuisine. When you are done exploring the city, you can take your tour beyond the city limits and take advantage of numerous options for outdoor adventures. If you love biking, hiking, and exploring the wonders of nature, be sure to check our guide to the area’s best trails.