After twenty-five years of regular trips to Portland, Oregon, I finally had the opportunity to visit the other Portland. So I headed cross-country from Southern California so I could finally visit Portland Maine. This would be my first trip to this city and state, and I was seriously excited. I’ve seen the photos of rugged coastline and lighthouses along with lobster boats galore, so knew I was in for a treat.
Most of my time in Maine was spent in Portland, a city that offers endless redbrick buildings, miles of cobblestone streets and plenty of scenic harbor views. Add in some fascinating history dating back over four hundred years and you’ll soon realize that this city packs a lot of sightseeing opportunities into a small space.
Want to venture out beyond Portland? Check out this itinerary for Midcoast Maine.
What to do in Portland Maine is unlimited, but most people have just a few days to visit, so I’ve narrowed the options to twelve--six are free and the six are not.
Keep in mind that the tourist season is May through October. Outside of those months, attractions and tours may be closed or have limited hours. If you're planning to explore more of Maine, be sure to order The Explorer's Guide To Maine.
Table of Contents
Start with a 90 minute overview
If you’re looking for fun things to do in Portland Maine, then The Real Portland Tour is for you. Derek--the founder of the company--is a local with terrific knowledge of the city, but he’s also a comedian. This is not your typical boring bus tour with a minimum wage guide hoping to go home soon. Instead, this is Derek’s passion project. He’s a college librarian during the school year and a tour guide on weekends and the summer season.
Most of this tour takes place inside the bus, which considering how cold the weather was, I seriously appreciated. But we did have two stops at the Portland Headlight and the Springpoint Ledge Light. I list this as the first thing to do on your visit because you’ll see the whole city in a short time period and get some ideas for what else to do in the coming days.
The Real Portland Tour is $27 for adults with discounts available for children and seniors.
Learn the history of Portland on a walking tour
I was a bit confused about booking a tour called “A Walk Through Time in Portland” with a company called Maine Foodie Tours, but there’s a good reason for this. One of the long-time guides, Mike, is so passionate about history, that his bosses finally let him have his own tour.
Despite the frigid weather (well it was frigid for a Southern California girl like me), Mike did an excellent job of keeping our attention for over two hours. He knows this city well and clearly enjoys sharing it. We began on Commercial Street and then wove our way through the Old Port district, downtown, and the waterfront.
Along the route tour guests will see Wharf Street, the home of Henry Wasdworth-Longfellow, the U.S. Customs House, the First Parish Church and several other historic landmarks.
Since Mike is also a local and a guide for the food tours, he’s likely to point out good restaurants along the way. (I personally appreciated his recommendation for the James Beard Award Winning bakery, The Standard Baking Company.)
The cost of this tour is $29.95 for adults and can be booked online.
Catch a Maine Lobster
I was so excited about my Lucky Catch Cruise, but concerned that it might not live up to expectations. I didn’t need to worry. This was a highlight of my time in Maine. I loved being on an actual lobster boat and being offered several opportunities to participate in the catch.
Captain Brian is a lobster fisherman most of the year, but sets aside the summer months to offer informative tours for visitors. During our cruise he gave an overview of lobster fishing in Maine as well as instruction in how to catch a lobster. He was accompanied by Kate, a highschool marine biology teacher who is well versed in both the natural and human history of the area. Combined, these two offer an excellent experience.
Did you know that 119 million pounds of lobster are caught off the shores of Maine each year? The first reaction might be concern for the well-being of these fisheries, but it turns out that Maine has some of the world’s best sustainability practices. As a result, we can all enjoy delicious Maine lobster guilt free.
The cost of a Lucky Catch Cruise is $35 per person. At the end of the cruise it’s possible to purchase the lobsters caught and then take them to a local restaurant to be steamed and eaten.
Be sure to book a cruise or sailing tour while visiting Maine!
Tour the Eastern Cemetery
Many years ago I visited several small cemeteries in Maryland with my parents as my mom was researching her family’s genealogy. This left me with a fascination of and appreciation for old and historic cemeteries on the East Coast.
Established in 1668, the Eastern Cemetery is the final resting place for around 4,000 people. In 1973 it was added to the National Register of Historic Places. Among the people buried here are Captains Blyth and Burrows, who fought against each other during the war of 1812, died as a result, and were interred next to each other. Also buried here are several men and women who were pivotal figures in the abolitionist movement of Maine.
A volunteer organization, Spirits Alive, offers walking tours of the cemetery from June through October for $10 a person. Guides will share the stories of Portland’s early residents as well as how the cemetery was originally divided into twelve sections in order to separate the deceased of different religions and races.
Explore the Portland Art Museum
If there’s an art museum in town then I’m going to see it. Fortunately the Portland Art Museum (PAM) was just a block away from my hotel and one rainy afternoon I stopped in to see what they had to offer.
Visitor’s to PAM get an especially good deal since they can see all the current exhibits and check-out the historic McLellan House on the museum’s campus. The house was built in 1800 by Major McLellan, owner of Maine’s largest shipping fleet and founder of its first bank. In one room is a timeline of the home and its series of occupants.
Among the several current exhibits I especially enjoyed the photography by Richard Avedon: Portraits, 1952-1970. The black and white portraits include Marilyn Monroe, Humphrey Bogart, Jimmy Durante, and others.
This place is definitely among the top Portland Maine attractions. Admission is $18 for adults and $15 for seniors and students. However, free admission is offered every Friday from 4-8 p.m. In a city where most attractions aren’t available off-season, it’s nice to know that this museum is open all year.
Eat and Drink Your Way Through Portland Maine
In 2018 Bon Appetit Magazine named Portland it’s Restaurant City of the Year. Had I known this before I arrived I might have added a few more days to my trip. Despite all the great meals I had in one week, I clearly did not have enough time in this foodie city.
Let me share just a few recommendations, starting with Eventide Oyster Co. If you love seafood, especially oysters, then find the time to eat here. I ordered far more food than originally planned, but glad I did so. I started with half a dozen oysters, then tried the Peekytoe crab bun and ended with the best tuna crudo I’ve ever had. The local beer I ordered to accompany all this food was also good, and the service terrific.
Hot Suppa is an ideal breakfast spot and I ate here twice. The first time I had the popular corned beef hash--which was definitely tasty--but my favorite was the waffle plate with eggs and canadian bacon. Top it off with real maple syrup and a good cup of coffee and I was in heaven.
I thoroughly enjoyed both the food and whiskey at Blyth & Burrows (named for the ship captains buried in the nearby Eastern Cemetery). From the charcuterie plate to the steamed buns and whiskey to the cocktails, this place did it all well. If you’re a fan of speakeasies, there is one in the back, but we hung out in the main restaurant.
Finally, for a restaurant known more by the locals than the visitors, head to Gilbert’s Chowder House and order the seafood chowder. The chunks of seafood were large and plentiful and kept me full for hours.
Can't decide where to eat? Try a Portland Food Tour!
Want to learn about the craft distilling scene? Try this Portland Craft Drink Tour!
Enjoy the Art and History of The Press Hotel
Among the many free things to do in Portland is the opportunity to enjoy history and art at The Press Hotel (frequently listed among the best hotels in Portland Maine). As the name suggests, this hotel was originally home to a newspaper publishing empire owned by Guy Gannett. Over the years it’s housed several different newspapers, a couple of radio stations, and one of the state’s first news websites.
Start in the lobby and appreciate how the newspaper theme is incorporated into the decor. Want to type a letter? There are old-fashioned manual typewriters available on a table along with paper. Then walk down the stairs and see the large scale installation on the wall featuring dozens of typewriters. Stroll through the downstairs hallway to see artworks from several local artists. If you get hungry or thirsty there’s a small cafe in the lobby and several comfortable seating areas.
Stroll Through The Old Port District
I’ll admit that the Old Port district can feel touristy, but there is some interesting history to explore here, so don’t be turned off by the t-shirt shops and candy stores.
My favorite section of the Old Port is Wharf Street. Look closely at the buildings and it appears that the windows on the second stories are large enough to be doors. Before much of this area was created through landfill, this street was actually along the waterfront. Those large windows were indeed the doors used to unload and load cargo from the ships. The cobblestones paving the streets were once the ballast that held empty ships steady.
Now Wharf Street is packed with popular restaurants, bars and nightclubs, so if you’re looking for lively nightlife, this is a great option.
Eat your way through the Old Port on a Food Tasting Tour.
After appreciating the historic buildings in the Old Port, it’s time to browse through the shops. One of my favorites was Cabot Farmers’ Annex. If you love cheese this place is for you. Cabot is a locally produced, award winning cheese--mostly cheddar--and its darn good. There are dozens of variations from jalapeno to everything bagel.
Book your Portland Maine tours today!
Get a great view of Portland and the Old Port District
Thanks to a tip received during a tour, I learned that one of the best places to photograph the Old Port area is from the top level of the Customs House garage, just across the street from the U.S. Customs House. So whether you’re an avid photog, or just like a great view, head to the elevator of the garage, take it to the top level and cross to the far corner. Looking down you’ll see hundreds of historic house and shops in the Old Port, as well as a great view of the harbor. I was fortunate to do this on a sunny day with blue skies.
Want a great camera that's easy to use? We use the Sony Alpha a6000 Mirrorless Camera.
Explore The Freedom Trail
It’s estimated there were 75 stops on the Underground Railroad in the state of Maine from the late 1700’s until the mid 1800’s. In case, like me, your U.S. history is a little rusty, it was during this time that slavery was legal in parts of the U.S., and illegal in others. As a result, attempting to escape to Canada was a tremendous risk, and were it not for the Underground Railroad providing protection and assistance, it would have been almost impossible to survive. Its believed that the railroad successfully assisted 100,000 escaping slaves.
In the city of Portland, the Freedom Trail is a self-guided tour of 13 places of importance during the time of abolition and the Underground Railroad. Stops include the Franklin Street Wharf where escaping slaves could board boats to Canada, the First Parish Church, home of several important abolitionists, and Abyssinian Church, a major hub of railroad activities.
A free map with details about each stop can be downloaded from the Maine Historical Society.
Looking for a guided tour of Portland? Check out all the great options here.
Visit and Photograph Lighthouses
Among the most popular things to do in Maine is visiting lighthouses. There are 68 lighthouses along the state’s coast, but if your visit is limited to Portland, you still have five to choose from. I had the opportunity to see three.
The most photographed lighthouse in the country, and the oldest in Maine, is the Portland Head Light in Fort Williams Park. Construction of this light was completed in 1791 and the keeper’s home was finished a few years later.
There is a small museum at the Portland Head Light, which while not free, is just $2 per person. Set amongst 90 acres of park land, this can be a nice stop for a few hours.
Opened in 1897, the Spring Point Ledge Lighthouse is located on the South Portland campus of Southern Maine Community College. Visitors can walk the 900 foot breakwater and experience a true working lighthouse. Volunteers lead occasional tours, so check the website for more details.
Portland Breakwater Lighthouse is the official name, but locals call is Bug Light. This small lighthouse was built in 1875 and modeled on a Greek monument. I had the opportunity to see this from aboard the Lucky Catch Cruise, but there is a paved walkway to the light for visitors.
Browse an Independent Bookstore
When writing about Portland, Oregon, I always encourage visitors to check out their independent bookstores, especially Powell’s. So I was excited to learn how many similar shops there are in Portland, Maine.
Right around the corner from my hotel was Yes Books. In all my time meandering through bookstores around the world I had never seen one so jammed packed with books. I almost hate to post a photo in case I inadvertently alert the fire marshall! While the size of this store is small, the impressively large inventory could keep a person busy for weeks.
Touted as Maine’s oldest bookstore, Sherman’s Maine Coast Book Shop is also worth a visit. This store does a nice job of featuring local and regional authors. While I didn’t make it to Longfellow Books, I understand this is much beloved by locals and well known for hosting author events.
Where to stay in Portland Maine
For this visit I selected the Westin Portland Harborview and would highly recommend it. The location was optimal for me. I walked to all of the restaurants mentioned in this article and many of the attractions. For Westin regulars you’ll know that the rooms are attractive and the beds truly restful.
One of the highlights of this Westin was their rooftop bar and lounge called Top of the East. Located on the 15th floor, this bar offered terrific views of the city and the harbor. I especially enjoyed the lobster sliders which paired nicely with a martini!
Visit Portland Maine
I started researching what to do in Maine months before my visit and haven’t stopped, even after being home for over a month. I fell in love with both this state and the city of Portland. I will definitely need to return to explore more and most certainly eat more. If you’ve never been, I encourage you to plan a trip here soon.