24 Hours in Portland, Maine

24 hours in Portland, Maine - View from Hyatt Hotel in Portland, Maine

For years, Phil and I heard close friends, coworkers, and family rave about the eclectic restaurants, electric nightlife, and energetic vibes hidden in Portland, Maine. Yet every time we planned a trip, these heartfelt recommendations seemed to slip our minds. But November 2016 was a special month for us: our five year anniversary! As a present to ourselves, we decided to treat ourselves with a weekend getaway, a special night where we could sneak away from our large metropolis and blend into a smaller city. This time, we both had the same thought – why not Portland? Once the decision was made our minds were filled with the thoughtful suggestions of others. Needless to say we were more than eager to spend 24 hours away from home and leave our mark on this quaint New England city.

We piled into the car with properly packed overnighters and drove 100 miles northeast of Boston on a crisp, fall Saturday morning. Our drive was smooth and easy as we zipped up Route 95. As the highway cut through seaside ports and winded through forests, we relaxed by soaking in the sun and sipping our pumpkin spiced lattes as we sang Michael Jackson’s greatest hits.

Considering I was born and raised a New Englander, I had my doubts about how walkable the city would the weekend before Thanksgiving – we’ve had snow on the ground by this time of year in the past. However, this unique city primely placed on a hill overlooking the ocean pleasantly surprised me. Though it was a bit past patio season, the city still glowed and was bursting with life.

Though it’s one of the smaller major cities in the Northeast, Portland, Maine holds it own. There aren’t many towns in the world where friendly college students, vivacious young families, and amiable townies congregate at a local haunt just for a brown paper bag of french fries cooked in duck fat. The cities that do have a vivacious culture usually don’t border the sea or are a 20 minute drive to one of the most picturesque, quintessential New England lighthouses on the coast. No, the Portland of the east is unlike any other.

Keep reading for our itinerary of how to spend a full 24 Hours in Portland, Maine. You won’t be disappointed!

24 hours in Portland, Maine - Cape Elizabeth Lighthouse

24 Hours in Portland, Maine

Key Pointers

  • Bring layers and comfortable walking shoes. As we like to say in the Northeast, if you don’t like the weather, just wait 10 minutes. Be sure to bring a lightweight jacket, a knit sweater, and a scarf that will easily fit in your bag. A hat may also be a great idea.
  • You can take the train! Phil and I drove the easy 2.5 hours from Boston to Portland, but you can easily hop on an Amtrak train in Boston and arrive in Portland in the same amount of time – and not have the hassle of parking a car in a city.
  • Though a car isn’t a necessity for this trip and the city is walkable, it may be worth renting a Zipcar for a few hours to drive around the outskirts of town or even head out to Cape Elizabeth. It’s worth the trip.

24 hours in Portland, Maine - Cape Elizabeth Lighthouse

Where to stay: Hyatt Place Portland – Old Port – this wonderful hotel is smack dab in the middle of the cutest shops and most delicious restaurants in Old Port/Downtown. The modern rooms are perfectly kept and come with all the amenities needed for your stay. Note: If you’re looking for peace and quiet, request a room on a higher floor facing inland. If you’re interested in breathtaking views of the old, brick cityscape request a higher front room, but fair warning it can get rowdy at night.

Where to eat, drink, and be merry:

  • The Holy Donut: The biggest, most delicious holey baked good in the city. Made with potato flour, these donuts come in the most eclectic flavors and are the size of your head.
  • Shipyard Brewery: If you are anything like us, beer is a must on every excursion, international or in our own backyard. In New England, Shipyard is known for its ‘Pumpkin Head’ brew in the fall months, but a tasting of four brews micro and mass produced for only $6? We were in. Be sure to grab a spot before heading to the bar. The place can get pretty packed and you don’t want to be stuck holding your flight.
  • Bonfire Country Bar: Western to it’s core, this bar has literal porch and tire swings to sit in while you munch on the free bacon and discounted drinks. The bacon is get it till it’s gone, usually around 5pm.
  • Duckfat: A cozy spot for a filling dinner or afternoon snack. This place, not only does it have delicious paninis made with organic, locally sourced produce, meats, and cheeses, they have fries. And not just any fries, potatoes fried in duck fat – twice. We are still dreaming of the poutine with tender morsels of duck meat in the gravy. A must!

24 hours in Portland, Maine - The Holy Donut

24 hours in Portland, Maine - Duckfat

24 hours in Portland, Maine - Duckfat

24 hours in Portland, Maine - Shipyard

What to do:

  • Support local businesses: Drop in The Mind Gift Shop, Motifs, or Abacus Gallery in Old Port/Downtown. They’re bound to have something special to remind you of the time you spent here.
  • Drive to Cape Elizabeth: Not only is the drive scenic, but Portland Light Head will take your breath away. Plus there are walking trails along the coast for miles – we spent the half a day here and it still didn’t feel like enough time.
  • Meander through Old Port/Downtown: The brick buildings have been kept in remarkable shape and feel rustic and industrial among the cobbled streets and old docks. It scenic town makes for a lovely walk, especially if you’re looking for some exercise – talk about hills!

24 hours in Portland, Maine - Downtown Portland24 hours in Portland, Maine - Cape Elizabeth Lighthouse24 hours in Portland, Maine - Shipyard

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