Is Portland, Maine on your Bucket List? There is so much to love about this city: the lobster, the lighthouses, and the history. The list goes on and on. After traversing the Old Port area for four days, I found a plethora of great destinations. For the most part, you can walk to the majority of these places. We did opt for an Uber drive for some of them.
While you’re walking the Old Port area, be sure to go down each alley heading to the water as they have surprises down each corridor: photo ops, ‘hidden’ restaurants, historical buildings, and docked fishing boats.
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Lodging
Black Elephant Hostel
The Black Elephant Hostel is an excellent choice for lodging in the Old Port area. The rooms are very clean, as well as the common area. They offer a full kitchen, garden patio area, indoor lounge area, and a tandem bicycle. Private and shared rooms are available. Bathrooms are shared among rooms. There is a place to store your luggage if you get here before check-in time.
Black Elephant Hostel 33 Hampshire St.
Airbnb
If you opt for an AirBnB, I recommend finding one as close to the historic downtown as possible. A lot of old homes have been converted into cozy little rooms with shared spaces. Many provide parking if you have a rental car. Portland is so pedestrian friendly that you can save your car for lighthouse sightseeing.
Tours
Portland Fire Engine Co.
I recommend taking this tour as one of your first activities. It really helps to set your bearings for the city and to give you an overview of what to come back and see later. The vintage fire truck will take you around town for about an hour with a guide pointing out interesting landmarks and telling fun facts about the area. Reservations can be made by calling 207-252-6358 or booking online.
Portland Fire Engine Co. 180 Commercial St.
Cemeteries
Eastern Cemetery
This cemetery dates back to 1668. It is open during daylight hours with guided tours available each evening by volunteers. There is a large banner by the entrance that gives details on obtaining tickets for the tours. I recommend the tours as they provide so much insight into the history of the headstones and the grounds in general.
VOLUNTOURISM: The Eastern Cemetery resets, cleans, and maps select headstones each year. You can join them in preserving history.
Eastern Cemetary – Spirits Alive Organization
Western Cemetary 2 Vaughn St.
Although not as old as the Eastern Cemetary, the Western Cemetary is pretty dated. There are also some pretty cool tombs that are embedded into the side of the hill.
Portland Freedom Trail
This self-guided walking trail runs throughout the city with markers located at various locations to give you further insight. Click on the trail link for a printable PDF map to help you. traverse the city.
Coffee Shops
With chilly temperatures a common situation, Portland has found respace in sipping a hot cup of coffee. There is no shortage on coffee shops, which makes it very fun to try out a new place each morning, and afternoon if you are so inclined.
Arabica Coffee Co. 2 Free St.
Located in the hub of Old Port commerce, the Arabica Coffee Co. serves up a tasty drink in real mugs. Chairs and barstools are available for patrons to enjoy their drink and pastry inside the restaurant.
Bard Coffee 185 Middle St.
Tiny but mighty is how I would describe this coffee shop. Bar stool seating where you can people watch through the huge windows or belly up to a group table. Vibrant colors and plants create an energized vibe. They even have a walk-up window if you want to stay outside.
Coffee Me Up 221 Cumberland Ave.
This neighborhood coffee shop is a few blocks away from the hostel. It serves a large variety of breakfast foods including a very nice array of pastries. There are a few patio tables on the sidewalk where you can sit and eat, otherwise it is takeout only.
Coffee By Design
There are several Coffee By Design shops throughout Portland. One is located a block or two away from the hostel. They serve delicious drinks as well as breakfast sandwiches and pastries.
The Holy Donut 194 Park Ave.
Have you had a potato donut before? I would suggest arriving before noon and be prepared to stand in line. The shop closes when the donuts sell out. With a wide variety of flavors, there’s sure to be a favorite. My top choice – chai. Yum!
Food
Portland Lobster Co. 180 Commercial St.
Oh, the lobster! Fresh lobsters are delivered to this restaurant twice a day. Their mussels are delectable as well.
Ruski’s Tavern 212 Danforth St.
Portland’s oldest pub, serving delicious food since the 1860’s, Ruski’s Tavern is a must. We stopped in for breakfast and it was fantastic. They served the best potatoes I’ve ever eaten.
Andy’s Old Port Pub 94 Commercial St.
The temperatures in Portland can drop quite a bit by evening. As you’re walking around the Old Port area, you might want to stop into Andy’s for a delicious hot chocolate. They often have live music up front, so it makes a great place for a pit stop to rest your feet.
Duck Fat 43 Middle St.
Duck Fat is located a block away from the hostel. Their made from scratch menu items are so good that we ate here twice over the four days in Portland. They are known for their Duck Fat Belgium Fries which come with various dipping sauces. Their Cream of Tomato Fennel soup was top notch, especially perfect on a chilly evening.
VOLUNTOURISM: Making a difference with everyday choices. When you order the Cubano Panini (which is delicious by the way), Duck Fat donates $1 to Full Plates – Full Potential to help end childhood hunger in Maine.
Portland Pie Co. 269 Ocean St.
When I visit a new city, I love trying the locals’ favorite pizza. Hands down, this is one of the best pizzas I’ve ever eaten. Pictured is the Bradbury Mountain.
Food Trucks
Falafel Mafia Food Truck
You’ve heard the phrase ‘When in Rome…’ a hundred times. Well, it holds true in so many places. When in Portland, grab some food from a favorite food truck and enjoy the harbor view. It’s about as perfect as things can get. And the food from Falafel Mafia is top notch deliciousness.
Bite Into Maine
I have to admit, I had sticker shock when I read the price of a lobster roll. After taking that first bite, I had zero regrets on the money I spent. So amazingly delicious!! Eating the lobster roll while perched on the rocks admiring the picturesque lighthouse is an authentic memory I feel every visitor should experience.
Gorgeous Gelato
I drink a lot of lattes. And I love gelato. What I didn’t know I was missing out on are affogatos. Oh, my. Your choice of two scoops of gelato with espresso poured over top. A perfect blend. It’s a great treat while visiting the lighthouse.
Murals, Sculptures and Architecture
This is self-explanatory but do keep looking up as you walk the streets. Walk on both sides of the streets and you’ll double your fun. The architecture is varied and historical. The element that struck me the most were the jaw dropping doors sprinkled all over town. It’s a constant treasure hunt.
United States Custom House 312 Fore St.
Now this place has some history! It used to sit right up next to the shoreline until the streets were added. Can you imagine the millions of people that have come through these doors.
Portland Observatory 93 High St.
One of only a few buildings that survived the horrible Portland Fire, the Observatory can be seen from almost every viewpoint in the city. Built as a communication point for the port, this clapboard structure is a stand alone icon for the city. Fun fact: There is not a single nail in this structure. It is all build with tongue and groove.
Portland, Maine Murals
There are murals to be found on the sides of buildings, down alleys and even in parking lots. One of my favorites was on the side of the Black Elephant Hostel. Bronze sculptures are found throughout Old Port. Each one tells a relevant story about life in Portland.
Boutique Stores
Ferdinand 243 Congress St.
This whimsical store has a little bit of everything, but mainly items made by the owner. It’s been in business for over 20 years. There are great deals on second-hand clothing, fun plants, and much more.
Knit Wit 247 Congress St.
They had me at the name. Portland had so many stores that used play on words for their business names. I loved it! Knit Wit has a large assortment of knitting yarns, patterns, and other essentials to create something beautiful and cozy.
Portland flea-for-all 585 Congress St.
A thrift store meets vintage clothing meets antiques meets plants pretty much sums up this awesome shop. Everything is so nicely displayed. It has a very airy feeling with a fantastic variety of every changing merchandise. *Only open on weekends.
The Maine Souvenir Shop
There are souvenir shops all over the Old Port area, but this one stands out for its variety of funny t-shirts, Maine specialty foods, and stickers.
Book Stores
Print: A Bookstore 273 Congress St.
A bookstore offering new titles for your reading pleasure. Located a few blocks away from the hostel.
Sherman’s Books and Stationery 49 Exchange St.
Sherman’s was established in 1886 and has been providing Portland and its visitors a variety of paper products ever since. This bookstore has a wonderful selection of both new titles, journals, and novelty items. It’s a great place to do some shopping for yourself and for others due to the wide selection of merchandise.
Lighthouses
Portland Head Light & Fort Williams Park 1000 Shore Rd. Cape Elizabeth
This iconic lighthouse is the bread and butter of Maine. It is absolutely stunning from every angle. Allow a few hours to be here as there is so much to take in as you walk the beach on one side and the rocks on the other. The rock formations are quite fascinating. They have the appearance of pressed wood. Tours of the lighthouse are given at select times. There is a parking lot at the park as well as food vendors.
You will also find the Goddard Mansion, which is an abandoned stone home and Fort Williams on the premises. Both are worth the time to go check out as they allow you to peak inside Maine’s amazing history.
Spring Point Ledge Lighthouse 2 Fort Rd. South Portland
My #1 piece of advice – Watch Your Step. Getting to this lighthouse is half the fun. Gigantic boulders are set side by side with 6”-12” gaps between them. The walk out to the lighthouse is very obtainable, you just have to really pay attention to where you’re placing your feet.
Portland Breakwater Lighthouse
and the Liberty Ship Memorial
Another one of Portland’s lighthouses, Bug Light/Breakwater Lighthouse is short and stocky but graced with beautiful architectural elements. Inspired by Greek architecture, the lighthouse is like no other in the world.
Near the parking lot, there is a fantastic static display depicting the history of the Ships for Liberty. South Portland was an emergency shipyard to help with the war effort from 1941-1945. During the war, 266 cargo vessels were constructed here by thousands of men and women.
Bug Light Park Madison St.
I’ve given you a quick rundown of 27+ things to check out while visiting Portland. Many of them are free and most are in close proximity of each other. There are many other places to explore in the general area, so pack a comfortable pair of shoes and have a fantastic time!
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