Portland Maine Day Trip Review

portland maine

A Visit To Portland Maine

As an airline pilot, I’m in new cities during layovers all of the time. I wish I could research each one before I visit, but that is sometimes impossible. That’s why this site exists. To help you make the perfect day out of your free time in a new city. In these posts, I try to write down all the information I wish I would have known. If there is something we missed make sure to add it in the comments below so others can take advantage of these tips too. Enjoy!

Oh, by the way, we sell all of our photography and you can visit the Portland Maine album here. Or, see all of our destinations here. Bloggers are free to use our images for their own posts with a do-follow link back to this page. 

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Despite not being the state’s capital, Portland is the most populous city in the state. When you visit, you will understand why. A mix of New England charm and culinary delicacy, I found Portland to be rich in culture and history.

The trip started with an amazing flight from Dulles to Portland. We took off north out of Dulles and turned easterly to fly over Washington DC at 10,000. Continuing up the coast we flew over Manhattan, Baltimore, Boston, and then up the coast to Maine. We enjoyed everything from seeing the huge metropolis of Manhattan island, the Statue of Liberty, Long Island, Martha’s Vineyard and then the cape and curling arm of Massachusetts. It was a beautifully clear day as we were finally cleared the Harbor Visual approach to Portland. We and the passengers enjoyed a very close view of downtown Portland off of our right wing as we turned the corner to our final approach over the lighthouses and forts in the islands outside of the cities harbor.

Things to do in Portland Maine

I quickly ran to my hotel room and changed while my Uber driver was coming to pick me up. Not knowing anything about Portland, I just picked the downtown area we had just flown over less than an hour before. Once downtown, visitors should walk the oceanfront as well as the downtown cobblestone area. Walking on foot is a very good way to explore the numbers shops, docks, restaurants, and many, many hole-in-the-wall bars.

Wharf in Portland Maine

The Wharf is located on the waterfront of the downtown area. Many boats will be docked next to the wharf. There are a few restaurants here and also some tourist boats for whale watching and ocean tours of the city. It won’t take you long to figure out why Maine is famous for its lobster. These ocean vessels are docked everywhere and are clearly a large part of the local economy.

These lobster traps literally feed the commercial sellers and local restaurants alike, which in turn feed our hungry and then very satisfied stomachs. Once served to inmates as a weird kind of torture, it soon became clear that these odd looking crustaceans were in fact quite the delicacy. During summers when the tourist season is in full swing, you can get a bite to-go at Portland Lobster Company right at the wharf.

Among many of the interesting sights the Long Wharf in Portland has to offer, the most unusual and maybe seemingly out-of-place is a small piece of the Berlin Wall displayed on one of its’ main oceanfront walkways.

Just North of the wharf, one can wander around the piers of the city and find a couple of iconic locations that are famous for showing the centerpiece of this city; the docks. At one particular dock, you can visit the Harbor Fish Market where the fresh catches of the day are sold wholesale through one door and retail through the other. Outside the door are three large sights with “Lobster,” “Fish,” and “Clams.” These certainly were a good sign of what one finds through this door; lots and lots of very fresh lobster, fish, and clams. Like a salty-fresh butcher shop, the smell of the sea permeates the building and will make your mouth drool with excitement to pick out your next meal.


Even if you didn’t bring your own cooler, that is just fine! The Harbor Fish Market will, for a very fair price, sell you an insulated box that is perfect for shipping your lobster, fish, or clams home. I joked I was going to bring some “emotional support” lobsters home in my lunch box and as I write this post am wishing I had. 


Downtown Portland Maine

The downtown area is very old and has a wonderful northeastern flavor. During the Thanksgiving and Christmas seasons, the cobblestone streets and walkways are accented with Christmas lights, wreaths, and other decorations. Hiding in this quaint beauty are many shops including The Holy Donut. Unfortunately, these Maine potato donuts had just sold out and when they are gone, as you can read in the window, “Sorry, we’re closed.” I guess I’ll just put that on my bucket list for next time.

Even if the donuts are gone, there is plenty of other great dining options too. Don’t forget, these restaurants are so close to the ocean that you can literally smell the sea salt from where your fresh oyster and lobster just came out of.

In the summers, there are more sidewalk foods and information booths for wandering tourists like myself. I walked by several places that were closed this time of year, but I did find this poor soul selling his hotdogs in the cold.

I don’t know if it was just me, but I saw what must have been dozens of local bars and ice cream shops. It seemed like every little basement, alley, and awning hosted a new venue. It makes sense that this vibrant scene is so strong because Portland is the beer capital of Main. Make sure you don’t miss your chance to discover some of these libations on your own. 

History of Portland Maine

There is an interesting history of Portland Maine. It was first settled by Westerners in 1623 by Captain Christopher Levett. By 1632 it was a permanent settlement set up to be a commercial fishing and trading village. But, in 1676 it was destroyed in the King Phillips War. About 100 years later it was once again burned down in the first year of the Revolutionary war by the Royal Navy but immediately after the war was over, the port became an important trading post and the citizens established ports where the modern downtown Portland is today. However, the history of this area was not yet finished drawing its modern borders. Portland struggled economically for several years during the Embargo Act of 1806 which prevented trade with Britain which was then compounded by the war of 1812. Portland had been the capitol city, but soon after this time, the capitol was moved north to Augusta.

Once again, in the mid 1800’s, Portland became an important trading port as the Grand Trunk Railway connected Portland Maine to Montreal opening a permanent ice free seaport access for Canada. By 1864 it was one of the northernmost battles during the Civil War. Then July 4, 1866, the city was burned to the ground again when an independence day celebration started the city aflame again. It was these multiple events where the city was destroyed and reborn that the cities motto is “We Shall Rise Again.”

Weather In Portland Maine

I visited during the week of Thanksgiving and was very comfortable in jeans and a light jacket. But in during the warm summers, tourists will find plenty to do including beaches, parks, boat rides; not to mention the walking tour I’m sharing with you. 

Summers are warm and wet, much like the American Midwest and the rest of the Northeast. Temperatures during the summer can reach 100 degrees but it averages about 80 for a high with nights in the 60’s. During the winter, average temperatures range from the mid-teens at night to about 35 during the days. The city gets approximately 4 inches of precipitation each month.

Restaurants in Portland Maine

Portland Maine really does have anything you want from Mexican food to Burgers and even a few Italian and sushi joints. But the one thing not to miss is the fresh seafood. It is a special food and a special place to enjoy it. Just like a margarita is a margarita, a margarita sipped on a Mexican beach takes on a whole new level and meaning the same margarita enjoyed in your cold Minnesotan kitchen. Even though you can ship all the fresh fish home you can imagine, you can’t get the same experience as eating it among the people who’s lives are so affected by this little harbor and downtown.  Take full advantage of the fresh, salty, savory experiences that are abundantly available in Portland.

To give you an idea of how strongly I feel about this I need to tell you a little story about an experience I had here. My Uber driver on the way home was telling me that earlier in day he drove a passenger from the airport to the downtown area who proceeded to eat two meals, and pack up several more to purchase in total no less than a dozen meals in to go boxes only to turn around and go back to the airport and his home in Dulles. Trust me, I wondered really hard if the guy was on my flight, but nonetheless, the lesson to take from this is to go on an empty stomach. 

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