Eating, Drinking, and Running in Portland Maine

Portland Maine

“The best way to explore a new city is to go for a run, or get lost.”

We’re running the red brick streets of the Portland Harbourfront.  It’s us, our guide, and three new friends who are visiting the city from Denmark. We’re all seeing the city for the very first time.

What to do in Portland Maine

It’s 7:45 in the morning, our first day in Portland. Our 20-year-old guide is a Portland local, and he tells us city stories and facts as we wind through the streets. The running tour is part of the standard summer offerings at The Westin Portland Harbourfront. It’s an excellent way to see the city, especially since the tour is led by someone who lives here.

I ask our guide what his favourite restaurant is. “That’s too hard,” he says, “Portland has the second largest number of restaurants per-capita, there’s so many great places.”Portland23

We finish the 5 km loop in the courtyard of the hotel, right in the city centre. The run is only scheduled each Friday, but our guide must have had as good of a time as we did, because he offers to do it all again tomorrow, this time with a different city route.

Armed with my new Portland knowledge (and feeling energized post-run), my parents and I take to the streets to see what other secrets Portland holds. We start with a peek at some of the history hiding right in the hotel. The property was built around three huge boilers made by the same company that built the ones in the ill-fated Titanic. They’re no longer in use, of course. Today, a few small computers perform the same task these once held.


I try to re-create my morning route, but the little shops and sights quickly take us off-course. We order a mocktail at Vina’s Fizz House, a soda shop that mixes up some pretty unique alcohol-free drinks, like this coconut, blood orange and ghost pepper blend.

What to do in Portland Maine


“Vena” was the owners great grandmother, who was involved in the Maine Temperence Movement in the 1900’s (which might explain the mocktails).

Everything I’ve heard about Portland has involved food or beer. So we cross the street and walk two blocks to Gritty’s to take in the latter. According to the sign, Gritty’s is “Maine’s Original Brewpub”. They also happen to be extremely dog-friendly, so we grab a spot on their patio and order a flight and a snack.



Portland Craft Beer

Two more blocks away, we find dessert at The Holy Doughnut. They use potato in their baked goods, and have a few gluten free options, including our pick, the Dark Chocolate Sea Salt.

Portland Doughnuts Gluten Free

Portland Doughnuts Gluten Free

Portland Doughnuts Gluten Free

And the Portland food scene extends to pets. Across the street we find the Gourmutt Beastro and Barkery. Earlier that day, The Westin staff had brought Charlie a cookie from the shop in the shape of a lobster. He ate all but the eyes in a matter of seconds.

Karen, the owner, greets Charlie before greeting us. “Let him off leash and let him pick any treat he wants, on the house.”

Charlie doesn’t quite know what to do with himself. He circles the store about six times before Karen serves him up a freshly baked maple bacon biscuit. She explains how she normally knows which treat dog-visitors want as their free treat.

“When they hop up in front of a plate and tilt their head, that’s the one they want.”

I purchase a few treats for the road – more of ‘his pick’, and a cupcake. It’s an “I’m sorry for forgetting your birthday last month” purchase.

Portland Dog Treats

We finish the day with dinner at yet another local craft brewery, Sebago. I order a sample tray to share with my Dad, and he and I both opt for burgers while Mom orders the seafood chowder.


Portland21The service is poor (could just be an off night), and while the burgers were okay we’re all generally unimpressed. It is the closest craft brewery to the Nova Star Port (the new ferry connecting NS and ME), but I’d suggest walking the extra four blocks to drink and dine at Gritty’s.

As we turn the corner leading back to our hotel, we’re just in time to see the end of a free two-hour swing lesson, complete with full brass band. Portland strikes me as the perfect blend of history and art. Plus, food. And having tried just four of the 200+ restaurants in this food and beer mecca, I have a feeling the adventure is just getting started.

Click here to read part two of this post for more great Portland eats, including a bar with a view of the whole city, and an amazing dog and kid friendly resto right on the water with most items ringing in at $4.

OR click here for the Portland pizza place so good, our customs agent recommended it to us at the border.


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About the author

The Local Traveler

Two travellers' tales of finding adventure on the East Coast. This blog is dedicated to the best parts of travel, and to discovering, celebrating and promoting things to do in our corner of the world, and sometimes beyond. We especially love craft beer, day trips, romantic escapes, local food & hidden gems. Join our community on Facebook, Twitter, or Instagram and share tips and photos of your favourite East Coast adventures.

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