24 hours in Greater Portland

June 29, 2019  •  1 Comment

Welcome to Portland, the largest city in Maine, known for being one of the “foodiest” places in America. The iconic L.L. Bean boots are a way of life here and are made only a few towns away. The economy here relies heavily on commercial fishing so if lobster and fish is what you desire you have come to the right place. If you enjoy breweries, the arts, shopping, outdoor activities, lighthouses, and beautiful scenic vistas then pack you bags for an exciting twenty-four hours (or more) in the greater Portland area!


So much to see and do and so little time. Start your day right with sunrise at the iconic Portland Headlight. This is the oldest lighthouse in Maine and possibly the most photographed lighthouse in America. After the final rays of light rise over the horizon take a short walk around the rest of Fort Williams Park for an up close look at late 1800’s military structures. Ram Island Ledge Light can be seen from the park as well.


On the way out of Cape Elizabeth stop in South Portland to see two more lighthouses. Southern Maine Community College campus is home to Spring Point Ledge Light, known for it’s 900 foot breakwater. This is one of the only lighthouses that you can take a tour of throughout the summer but you should check the schedule for details. Make sure to wear comfortable walking shoes; navigating the giant granite boulders that make up the breakwater could be treacherous if not wearing appropriate footwear.


About 5 minutes down the road is Bug Light. This lighthouse is much more accessible and has a spectacular view of Portland Harbor. This is a great spot to sit and watch ships come in and out of the harbor, from sailboats to giant cruise ships.


If you are looking to cool your heels on a southern Maine beach, you have a few options:

  • Willard Beach in South Portland is great but be aware that many people bring their dogs

  • Crescent Beach State Park in Cape Elizabeth is very family friendly

  • Higgins Beach in Scarborough has some of the best surfing waves in the State

  • Scarborough Beach in Scarborough is generally not as populated as other beaches

  • Old Orchard Beach in Old Orchard Beach is one of the most popular beaches in Maine with the pier being it’s predominate feature

If you are driving or renting a car remember that most places in the greater Portland area require you to pay for parking. If you are able to use a smaller vehicle that may make it easier to parallel park or get in and out of parking lots in downtown Portland.


When you head back into Portland you will find an abundance of food stands, restaurants, and breweries located in the Old Port. The Old Port is a historic district with cobblestone streets and brick buildings. There are clothing boutiques, souvenir shops, art galleries, and of course restaurants and other gourmet food stores. This area is the nightlife capital of the state as there are multiple pubs, breweries, cocktail bars, and nightclubs.


With so many food options I am going to share some of my favorites:


  • Becky’s Dinner It may look like a hole in the wall, but it is an iconic local favorite. They serve breakfast from 4 AM until 4 PM and you cannot go wrong with any of their daily specials.

  • Duckfat – if you’re looking for a quick snack, I would highly recommend stopping by and ordering a plate of poutine here. Make sure to add pulled duck meat and an egg to your order...delicious.

  • Bingas StadiumThis is a sports bar with forty beers on tap and is known for their wing sauces. There are over thirty sauces to choose from and if you like wings you have to give this place a try! The original Bingas burned down 2008 but that didn’t stop them. They rebuilt the restaurant and created a new super hot sauce as a tribute (’08 Fire) which “makes women scream and grown men cry”.

  • Benkayfor all you sushi lovers out there you should definitely stop here. They have some of the best and most fresh sushi around.

  • Sebago Brewing Company – My favorite brewpub in the state... ‘nuff said.

  • Nosh Kitchen Bar – If you are looking to try something completely outside of the box check out this place. They pride themselves on having all natural meat and produce and “badass french fries.”

  • DiMillo’s – If you are going to get seafood it might as well be from one of the best and historical restaurants in the city. Seafood doesn’t get any more fresh than this as the restaurant is a large floating boat located right on the wharf. This restaurant is a little more pricey than standard fare, but your stomach will thank you. I would recommend making a reservation during peak tourism season.

  • The Grill Room – If you are more of a steak and potato kind of person then look no further. The menu is on the expensive side but is completely worth it. It was good enough for me in fact that I said yes after my husband proposed to me here. Reservations are recommended.

  • Or you could always take a craft beer tour

Make sure to take a stroll up and down those cobblestone streets to the different shops and galleries that span the entire downtown area. You are bound to find something that piques your interest to take home to your family.


If you really want to experience a view of the city, you should take a trip up the Portland Observatory. The eighty-six foot observatory was constructed as a communications station for the Portland Harbor in 1807. The observatory is the only remaining historic maritime signal station in the United States.


There are multiple civic centers in the area that are worth checking the schedules for including:

  • Cross Insurance Arena

  • The State Theater

  • Thompson’s Point

  • Merrill Auditorium

  • Portland Stage Company

  • Hadlock Field (home of the Portland Sea Dogs minor league baseball team)

Book a sunset sail on the Eleanor Hawkes with Captain Ian Glass and ‘Sail Portland Maine’. I did this sail a few weeks ago and it was a great experience. I have lived on the Casco Bay for over seven years but have never experienced it like this. Captain Ian is professional and gives you an intimate tour of the bay. He only takes six people out at a time, so it is bound to be a personal experience that you are not going to forget. Not only are the views incredible but he prepares fresh oysters and wine on for the sunset excursions. If it happens to get a little chilly out on the water wool blankets are provided for you. If you’re lucky, he might even let you take the wheel. Keep a watchful eye on the bay or you might miss the playing seals!

Sit back, relax, eat, drink, and feel the wind on your face as you take in the beautiful sights. There’s no better way to watch the sun go down.


After returning from the sunset tour you could check out one of the many night clubs in town including Oasis, Aura, or Pearl and dance the night away.


There is so much to do here, but this should be plenty to get you through your first twenty four hours. If you go to bed exhausted and wanting more, I have done my job. If you have any questions or want more information, don’t hesitate to ask! Enjoy your stay in Portland Maine!


Safe Travels and Happy Adventuring!

-KT (globetrotter_kt)


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Gayle Kosches(non-registered)
Your work is beautiful. Your writing is cohesive and fluid while enabling the reader to dream along. Please don’t ever doubt your talent or second guess your creativity. There will always be an audience of “lovers” and whatever the opposite may be. Be true to your vision. As an additional comment, my daughter is also KT- Katie for years; as well as Kit Kat by the family.
We were in southern Maine earlier this month and will certainly visit Portland very soon.
Best regards,
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