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Duffel Bag Spouse Travels

Travel + Wellness + Culture + Women Over 50

Old-Port-District-Portland-Maine

How to Spend 72 Hours in Portland, Maine

Posted on January 12, 2020November 16, 2025
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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.

This post is sponsored and/or contains affiliate links, from which I earn a commission at no extra cost to the reader. I appreciate your support and know that all the views expressed are my own.

  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 Maine Portland Lobster Co

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.

Ironclad Coffee and Roastery: 100 Year-old Fire Station in Richmond

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.

 
 
 
 
 
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#wits19 in Portland, ME loving that seafood life swimming in garlic butter and a side of cheesy bread. #dippingisnotonlyallowedbutrequired #blackgirltravels to the Maine women in #travelsummit #foodheaven #girlstrip2019 #alltheseafood #mussel-madness— where’s the love?

A post shared by Stacey Peters (@duffelbagspouse_travels) on May 5, 2019 at 3:03am PDT

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.

Santorini– A Quick Flight from Baumholder Germany

Check out another favorite American City– How to Do San Francisco on the Cheap.

Portland Maine Old Port District 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

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 Maine

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  1. Stacey Peters says:
    May 5, 2020 at 3:16 pm

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