22 Jun Portland, Maine Walking Tour: 6 Tours to Book Today

Instead of exploring the city on your own, why not let expert guides lead you on a walking tour of Portland, Maine to the best spots for food, desserts, history, lighthouses, and more? There are a variety of walking tours available, so you are sure to find one that suits your preferences. For example, maybe you want a walking tour centered around history or one centered around drinking. Well, there are specific tours for each of those! Keep reading below to learn more about those options as well as a few others.

Contents:

1) Best Tour for Food

2) Best Tour for Drinks

3) Best Tour for Sweets

4) Best Tour for History

5) Most Unique Tour

6) Self-Guided Tour

7) Bonus: Best Biking Tour

1) Best Tour for Food – Portland Maine Walking Tour

Of course one of the best options for a Portland, Maine walking tour has to be centered around food. You might already know that Maine is known for some seafood items, such as lobster and clam chowder. However, are you ready to learn even more about the unique foods of Maine? If so, then book the Old Port Culinary Walking Tour today. Taking a culinary tour through Portland is even considered one of the top things to do in Portland, Maine.

If you find yourself in Acadia National Park in the future, definitely head to Bar Harbor and order seafood, including a lobster roll. Then you can even compare your lobster rolls to see whether Portland or Acadia win with the most delicious one!

Price and Time 

First, the price of the foodie walking tour in Portland, Maine is approximately $140 per person. While this might seem a bit expensive, keep in mind that you are tasting food from multiple different places. If you went out yourself and bought meals from each place visited on the walking tour, you would probably end up spending just as much if not even more. Another way to think about the tour is that you are essentially booking a free walking tour of Portland, Maine and just paying for all of the food you are going to eat along the way.

Second, the tour lasts around three hours. They recommend you park in a nearby garage due to the fact metered parking has time limits.

General Information

Come hungry to this foodie walking tour, for you will be tasting all of the unique flavors of Portland, Maine. A guide leads the tour group around Old Port, which is a neighborhood located in the heart of Portland, Maine. They tell you stories about the food scene in Portland, offering insider knowledge only known by locals themselves.

Additionally, the tour stops at up to seven different food places. These are not just your average food joints, but rather they are hand-selected as some of the best in Old Port, offering flavors unique and local to Maine. You have the chance to sample food at each stop, which means you will likely have a full stomach by the end.

Link to tour booking: Old Port Culinary Walking Tour.

On the other hand, consider the Old Port Seafood Lovers Walking Lunch Tour if you are looking for a tour focused solely around seafood.

Lobster roll from Bite Into Maine food truck

2) Best Tour for Drinks

Second on the list of the best Portland, Maine walking tours is the Old Port Brewery Walking Tour. Why not book a tour all about drinking after you finish the tour mentioned above that is all about eating?

Price and Time – Portland Maine Walking Tour

First, the price of the tour is approximately $89 per person. This might seem a bit steep for a brewery tour, but keep in mind the price includes a few drinks along the way.

Second, the tour lasts around three hours. You might want to park in a nearby garage due to the fact metered street parking has time limits.

General Information

A guide leads the tour group to three different breweries around the neighborhood of Old Port in Portland. They provide all kinds of fun facts and historical information on the brewery scene in Portland, which is more active and blossoming than most people assume.

Moreover, the Old Port Brewery Walking Tour includes a sample at each brewery stop. Do a little bit of math, and that is three free beer samples throughout the duration of the tour. If you do not like beer, they sometimes also offer seltzers, ciders, etc. Check with the tour company for more information. Additionally, the tour includes a small snack at one of the breweries.

Link to tour booking: Old Port Brewery Walking Tour.

3) Best Tour for Sweets – Portland Maine Walking Tour

The best Portland, Maine walking tour list would not be complete without the Donut Tasting Walking Tour in Old Port. Maine is well known for whoopie pies, but what might surprise you is that they are also well known for donuts. For example, did you know that the donut was invented in Maine?

On the other hand, head to the Kindred Farms Market and Bakery in Casco if you are on a search for the best whoopie pies. I can still remember my first bite of a whoopie pie from there…maybe it is a good thing I do not live nearby. I would be getting one (or five) too many whoopie pies a week.

Price and Time 

First, the price of the tour is approximately $50 per person. In my opinion, the price is well worth it for all of the donut samples you get to enjoy on this foodie walking tour of Portland, Maine.

Second, the tour lasts around one hour and 15 minutes.

General Information

During the Donut Tasting Walking Tour, a guide leads you around the neighborhood of Old Port in the city of Portland. They provide you with all kinds of information concerning the donut scene as well as the history of donuts in Maine.

Moreover, the tour includes stops at three different donut shops within Old Port. These are hand-picked as some of the best donut shops in the area. Oh, and did I mention the tour also includes six donut samples?

Link to tour booking: Donut Tasting Walking Tour in Old Port.

Whoopie Pie from Kindred Farms and Bakery

4) Best Tour for History 

If you love learning about the history of new places, then check out the Portland Hidden Histories Walking Tour. Within just two hours you can learn a wealth of information on the city of Portland. You will then be eager to share your newly-learned facts with friends and family.

Price and Time – Portland Maine Walking Tour

First, the tour costs approximately $50 per person. Honestly, paying $50 for the tour is well worth it since you would have to spend hours and hours researching to learn the same amount of information.

Second, the tour lasts around two hours.

General Information

The Portland Hidden Histories Walking Tour includes an expert guide to lead you around the neighborhood of Old Port as well as downtown Portland. The time of the tour is split between the two locations with one hour walking in Old Port and one hour in downtown Portland. Historical stops include the US Custom House, Portland Pier, Foundry Lane, Monument Square, First Parish Church, and more.

As you walk around, the guide offers all kinds of information from the 400 year-old city of Portland, Maine. You might even learn a few things that surprise you.

Link to tour booking: Portland Hidden Histories Walking Tour.

Cute street in Portland, Maine

5) Most Unique Tour – Portland Maine Walking Tour

Last up on the Portland, Maine walking tour list is the Portland Crime and Injustice Walking Tour. This tour is a bit more unique due to the fact it does not really fit into any of the four categories mentioned above. Instead, it highlights exactly what the name states – crime and injustice.

(Sometimes the Portland Crime and Injustice Walking Tour shows as unavailable on TripAdvisor. If that is the case for the dates you plan to visit, then check out the Walk With Ghosts in Portland Tour).

Price and Time 

First, the price of the Portland Crime and Injustice Walking Tour is approximately $50 per person. A small price to pay for learning a bunch of interesting information.

Second, the tour lasts around two hours.

General Information

An expert guide leads you along a 1.5 mile (~2.4 kilometer) path through Congress Street National Historic District, Arts District, West End, and Old Port within Portland, Maine. In terms of time, you spend 45 minutes in the Congress and Arts Districts, 45 minutes in the West End, and 30 minutes in Old Port. Some example stops within these areas include the Chestnut Street Church, Congress Square, Victoria Mansion, Gorhman’s Corner, Tommy’s Park, and more.

As you walk along, the guide provides all kinds of interesting and historical information on topics such as enslavement, human trafficking, drowning, arson, and more. Due to the topics of information, only children aged 15 and older should attend the tour. Moreover, I recommend you look into all of the topics they cover to determine if you have a sensitivity with a certain topic they plan to expand upon. You can find more information on their booking page listed below.

Link to tour booking: Portland Crime and Injustice Walking Tour.

Maine Lobsterman Statue in Portland

6) Self-Guided Tour

The only negative aspect of a tour is that you usually have to go at the pace of the tour company. However, you can create your own pace on the self-guided Audio Guided Walking Tour from Old Port of Portland, Maine.

Moreover, it is no problem if you get distracted by other nearby attractions (or food) as you follow along the audio tour. The world is your oyster (or lobster roll, we are in Portland, Maine after all).

Price and Time – Portland Maine Walking Tour

First, the tour costs approximately $8 per person. You read that right – only $8! If you are on a budget, then this self-guided walking tour of Portland, Maine is the perfect choice.

Second, the tour lasts around one to two hours. However, please remember that the tour is self-guided. You can thus spend as much or as little time as you want walking through the different attractions.

General Information

The Audio Guided Walking Tour of Portland, Maine includes a narrated audio tour available through an app on your phone. The narrative includes information on 10 different locations in Portland: (1) Berlin Wall (2) Exchange Street (3) Wharf Street (4) Wadsworth-Longfellow House (5) Post Office Park (6) Lobsterman Park (7) Congress Street (8) Holy Donut (9) Lincoln Park (10) US Custom House.

Whew, that was a lot! For a sneak peak, the audio tour highlights the history of the lobster industry in Maine, the hype behind Portland’s most beloved donut shop, and so much more. Each stop on the tour has a narration of approximately five to 10 minutes associated with it.

Link to tour booking: Audio Guided Walking Tour from Old Port of Portland, Maine.

7) Bonus: Best Biking Tour in Portland, Maine

I know this is not a walking tour, BUT biking is another great way to see the city and its main attractions. The Portland Bicycle Tour with Lighthouses and Lobster Roll is the perfect tour if you want to prioritize visiting lighthouses.

Price and Time 

First, the Portland Bicycle Tour with Lighthouses and Lobster Roll tour costs approximately $160 per person. Moreover, that price includes the use of a bicycle, a meal, and all applicable lighthouse entrance fees.

Second, the tour lasts around five hours. You might want to park in a nearby garage due to the fact metered street parking has time limits.

General Information

Once you all hop on your bikes, the guide leads you around Portland at a leisurely pace, highlighting its main attractions. First, you stop at Bug Light Park, which has the Portland Breakwater Lighthouse (aka Bug Light). Second, you stop at the Liberty Ship Memorial where you learn some history about World War II. Third, you stop at Fort Williams Park to see Portland Head Light (another lighthouse) and eat lunch. The lunch is included in the tour price and includes a lobster roll, chips, soda, and dessert.

Fourth, you bike through the town of Cape Elizabeth where you pass by some magnificent houses on the water. Fifth, you stop at Willard Beach for a couple of minutes after biking through Willard Square. Sixth, you make your final stop at the Old Port neighborhood within Portland. After the tour ends, feel free to spend some more time here as you peruse the shops and restaurants.

Link to tour booking: Portland Bicycle Tour with Lighthouses and Lobster Roll.

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Do not miss out on this waterfall near Rangeley Lake State Park: Smalls Falls in Rangeley, Maine.

Also, be sure to check out my favorite waterfall in Maine: The Cataracts: Set of Three Waterfalls.