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.

Table of Contents

Getting from the Airport

My hotel offered a free airport shuttle, but I called an Uber. My back hurt, and the shoes I packed were not comfortable enough. I needed shoes that worked for the conference without making things worse. I went shopping at the Maine Mall in South Portland. It had more than 100 stores, a directory, and free Wi-Fi. I found several options there.

Where I Stayed

I stayed at the Westin Portland Harborview on High Street. The hotel gave me easy access to Portland restaurants, shopping, and the arts district. It also had a rooftop bar overlooking the city and a fitness center. I used the fitness center each morning. Morning workouts had become part of my routine when traveling.

Where I Ate

Portland gave me plenty of opportunities to eat seafood. I tried lobster, mussels, and shrimp, often with plenty of butter and garlic. I also found restaurants serving sausages, tacos, and doughnuts. The variety surprised me. Portland offered more than the familiar lobster roll, although I enjoyed that too.

Portland Restaurants to Visit

Porthole — 20 Custom House Wharf
I enjoyed lobster bisque and mussels near the waterfront.

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

Street & Co. — 33 Wharf Street
The shrimp came with butter and garlic. Reservations were suggested when I visited.

Thirsty Pig — 37 Exchange Street
This casual spot offered house-made sausages, vegetarian sausage, beer, and signature cocktails.

Holy Donut
This doughnut shop uses potatoes in its recipes. I found it near the harbor on a cobblestone street.

Taco Escobar — 548 Congress Street
This small Mexican restaurant sits near the arts district. Try the crispy carne asada tacos. The pineapple poblano and toasted coconut-infused tequilas also caught my attention.

Things to See and Do

The conference occupied most of my weekend. Still, I made time to walk through the Old Port District. Cobblestone streets led toward the working harbor. Historic buildings stood alongside shops and restaurants. The nineteenth-century architecture made the area especially interesting to photograph. Portland has more neighborhoods worth visiting. Congress Street has an arts district. East Bayside and Munjoy Hill add different sides of the city. I did not have enough time to see everything.

Grace Restaurant

On my first night, I met other conference attendees at Grace Restaurant. The entrance caught my attention immediately. Massive red doors displayed the name Grace. The restaurant occupied a former United Methodist church. Inside, I saw soaring ceilings, restored woodwork, and 27 original stained-glass windows. The building dates to 1856 and features Gothic Revival architecture. It was an unusual setting for a cocktail party. I enjoyed seeing the old church transformed into a gathering place.

Final Thoughts

My three days in Portland did not unfold as planned. Back pain limited my comfort, and conference sessions filled much of my schedule. Still, I ate memorable seafood and enjoyed the Old Port streets. Portland definitely deserves more than a few hours between meetings. I would return with comfortable shoes and more time to wander.

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