Crew Guide to Portland, Maine

If you’ve had the pleasure of visiting the neighboring New England cities of Boston and Newport, you’ll know that Portland, Maine, is decidedly rustic, quaint, and down to earth. Unlike places farther south, there’s no who’s who this far north in the country; it’s mostly simple living, a love for the outdoors, and fantastic breweries.

How to Get There

Getting to Portland are the usual options as per most U.S. cities: plane, auto, or rail. However, if you’re already somewhere close on the East Coast, rail is always the most underrated option. More spacious than a bus or flight, the views you’ll get along the way beat the other options hands down, especially if taking a coastal track.

Where to Stay

Old Port is the choice neighborhood to stay in, as you’ll be stepping out onto cobbled streets, salty air, and the thrum of the city. However, most stays in the area are the usual suspects: Hilton, Hyatt, and the like. As Portland is almost entirely a summer tourist town, book your Airbnb well in advance. There’s not too much of a boutique-hotel scene, but a place called Pomegranate Inn is pretty consistently popular.

Enjoy the Brews

Portland, sharing its name with a city in Oregon, is both home to some of the best breweries in North America. In fact, you’ll run out of time in the city before you run out of great IPAs to sample. Allagash Brewing Company, as the largest and one of the most established craft breweries in the state, is a good place to start. Unless your heart is set on one of the multitudes of other breweries — Rising Tide Brewing Co, Maine Mead Works, and Lone Pine Brewing Company, to name a few — a great option is to just take a brew tour. Check out Maine Brews Cruise for plenty of organized walking, biking, and bussing tours.

There’s also just as many local coffee shops as there are breweries, many with their own roasts. Coffee ME Up, Bard Coffee, and Arabica are all town favorites and have been for many years.

Where to Eat

Great seafood dining is to be expected in a historical seaport, especially at the likes of Portland Lobster Co. Somewhat of a gem seems to be a European-style eatery called Duckfat, which serves pretty unbelievable milkshakes and the best poutine I’ve experienced outside Canada. Takeout is always an option as getting a table was just about impossible during all three of my visits (yes, the poutine is that good).

What to See and Do

The Portland Museum of Art, as you can expect, is a great sample of the city’s more formal art scene; however, it’s also well worth your time to take a wander around the Art District and pop your head into the many small, local art supply stores — they usually showcase prints and canvases by the local talent. You can also find some more local handiworks at the markets in Deering Oaks Park on Saturdays during the summer. You’ll have to find them though; they’ll be amongst the cheese, honey, fresh berries, baked goods, and just about every other produce you can think of that will also be on display at the stalls. Sampling is highly encouraged. Check out Portland’s website for a full list of farmers’ markets and other events. There’s even a whole week in the summer to celebrate the kelp harvest, Maine Seaweed Week.

Somewhat unexpected is the extensive trail network the city offers, which I would expect to find in the likes of Colorado, constructed and maintained by Portland’s non-profit land trust. (Check out their Instagram @portlandmetrails where there’s a link for a digital map of all the trails.) Almost all trails are bike-friendly too. At some point during your time, take the East Promenade Trail along the eastern waterfront for one of the best walks in the city.

And on the off-chance you’re a fanatical squash player like me (it’s similar to racquetball), Portland has one of the most thriving squash communities I’ve come across. They host four brand-new courts at Portland Community Squash, some of the best courts in New England.

This article originally ran in the November 2021 issue of Dockwalk.