How to Spend 72 Hours in Portland, Maine


Seventy-two hours in Portland, Maine, and I’m in excruciating pain. I don’t know why my back has decided to act up a few weeks before my long weekend trip to Portland. But I’ve already paid for the conference, hotel, and airfare. So I’m loading up on nerve blockers and pain meds, and I’m going to Maine. I’m going to a blogging conference in Portland, Maine.

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  1. From the airport to the hotel
  2. Where I Stayed
  3. Where I Ate
  4. List of Portland Restaurants
  5. Things to do in Portland
  6. A Unique Venue

Portland-lobster-cafe-1024x615 How to Spend 72 Hours in Portland, Maine

72 Hours in Portland, Maine
Getting From the Airport

Although the hotel offered a free airport shuttle, I called an Uber. My back was killing me, and the shoes I brought weren’t going to suffice. I needed to find some comfort, but cute shoes for the conference. I found several options at the Main Mall in South Portland. There are more than 100 stores, an online directory, and a map and free Wi-Fi.

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Where I Stayed

I stayed at the Westin Portland Harbor View on High Street in the Old Port District. The hotel is in a great neighborhood full of arts, shopping, and restaurants. Some of the amenities include a rooftop bar with extensive views of the city, a fitness center– which I used every morning. I enjoyed my workouts in the morning. It’s something I’ve gotten used to when I travel.

How to Spend 72 Hours in Portland, Maine

Where I Ate

I got a chance to sample a lot of the seafood made famous by Portland’s location on the ocean. These are the highlights and what I ate. Portland’s reputation as a great dining town is well-deserved, and choices are abundant with fresh takes on everything from doughnuts to kombucha.

List of Portland Restaurants to Visit

Porthole, 20 Custom House Wharf. I enjoyed a delicious lobster bisque & mussels.

J’s Oyster, 5 Portland Pier. I had a lobster roll that was bigger than my face.

Street & Co, 33 Wharf St. The shrimp in butter and garlic, reservations suggested.

Thirsty Pig, 37 Exchange St. Inexpensive signature cocktails, beer, and house-made sausages, veggie sausage

Holy Donut, Located near the harbor on a quaint cobblestone street and made with natural ingredients including potatoes.

Taco Escobar, 548 Congress St. is a small Mexican restaurant near the arts district. Try the crispy tacos with carne asada. Take a risk and ask for the pineapple poblano or toasted coconut-infused tequilas.

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Old-Port-District-Portland-Maine How to Spend 72 Hours in Portland, Maine

Things to See and Do

72 Hours in Portland, Maine

The conference took up most of my time, but I did get a chance to explore the Old Port District. With its cobblestone streets and photogenic harbor. Portland’s Old Port district has lured travelers seeking a quick dose of urban New England waterside charms.

There’s a stunning array of 19th-century architecture. The city has a layered history. Portland’s allure spreads to the Congress Street arts district and the Indie-spirited neighborhoods like East Bayside and Munjoy Hill. And seafood takes center stage n all of them.

72-Hours-in-Portland-Maine-Lunch-at-Porthole How to Spend 72 Hours in Portland, Maine

Grace Restaurant

I met my conference crew the very first night at a cocktail party at the Grace Restaurant. The building with its massive, red doors bearing the word “Grace” scrolled across the entrance, confused me. The former church is now a sophisticated restaurant. But the mysterious triangular logo could be forgiven for thinking they had stumbled upon some kind of new-age congregation. Grace Restaurant was once a former United Methodist church downtown.

I stepped through the entrance, into the soaring ceilings 27 original stained-glass windows, and painstakingly restored woodwork inside a landmark 1856 Gothic Revival.


72-Hours-in-Portland-ME How to Spend 72 Hours in Portland, Maine

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