Portland: Maine’s Stalwart Seafaring City

By Kent E. St. John
Senior Travel Editor

A lobster boat casts off in Portland Harbor. Photo by Kent St. John
A lobster boat casts off in Portland Harbor. Photo by Kent St. John

Portland, Maine is scruffy in the most desirable way; no wonder Outside Magazine places it on the 2005 list of the best places to live. That fits with its motto Resurgam (I shall rise again).

Just past the affluent Kennebunkport and south of LL. Beanville (Freeport) lies one of America’s fastest growing revival cities. The downtown area is filled with shops, pubs and fishermen. Greek revival mansions sit side by side with brick bastions that once served the seafaring Mainer.

The town is gruff; brick architecture exemplifies the hard-working heart of this seafaring town. Portland may have a nightlife riddled with top restaurants and top names of every venue the entertainment world has to offer, but its exterior is the glossy coating of a 19th century stalwart fishing village gone metro.

When the name Portland comes up, nine times out of ten people think of this breezy city’s west coast Oregon twin. Hidden away in plain sight, however, is cultural restoration at its finest.

The largest city in Maine, population 230,000, Portland is its best-kept secret. While most tourists scour the coast for hot spots like Bar Harbor and Old Orchard Beach, Portland stands as a bastion for this country’s past embracing its future. Spread out in view from the harbor is Casco Bay with multiple islands.

An aerial view of Downtown Portland by Gordon Chibroski of FreelantzImages.com
An aerial view of Downtown Portland by Gordon Chibroski of FreelantzImages.com

Old Town Portland

The several square-block section of the city is visitor-perfect yet it is obvious that it was redone for the inhabitants. The old Victorian-style buildings blend with eateries and usable shops.

The waterfront sits nearby and it is clear that the sea is king. The Harbor Fish Market at 9 Custom House wharf is testament to that.

At night the locals head to pubs such as Gritty McDuff’s and Dewey’s to gab and throw a cold one back — Portland was spot on with the brewpub! The Portland Public Market keeps step, with its vendors selling the best food that Maine produces. It also houses restaurants and coffee shops.

The Portland Museum of Art is on Congress Square and boards some Homer, Hopper, and Wyeth. A great surprise was the Renoir, Degas, Matise and Picasso works. In a five-story building sits the Maine College of Art (MECA) which anchors the Arts District.

Two House Park - photo by Kent St. John
Two House Park – photo by Kent St. John

Longfellow Square nearby is a mix of art galleries and antique shops. Lodgings range from simple to grand and the ability to walk the city a big plus. End a city crawl with a visit to the Allagash or Casco Bay Breweries, you’ve earned it!

Dining in the city can be as plain or as fancy as you choose, and all is quality. Bad restaurants do not last here. In fact, Portland has the highest number of restaurants per capita of any city in the US. Some of my favorites were very low-cost in comparison to quality, rare in a US city.

Gilbert’s Chowder House with a dive look offered fantastic clam chowder and, in season, tables on the wharf. The nearby Porthole was dive divine and had seafood specials that were simply great.

If veggies are your thing try Bella Cucina or Flatbread Pizza. The big gun in downtown is Fore Street; it put Portland dining on the national map. The former brick warehouse serves local, organic and seasonal. Portland is a “pick your own after dinner” activity place.

A Casco Bay lobsterboat - photo by Kent St. John
A Casco Bay lobsterboat – photo by Kent St. John

Shipping Out

It would be a crime not to take advantage of Portland’s waterfront location. Fortunately that is easily done several ways. My favorite was aboard some of the Casco Bay Line ferries.

This company was the longest continually-running ferry company when it went bankrupt in 1984. Like the rest of the city it is back bigger than ever. It provides year-round support to six of the many islands off the city. Off-season it is possible to take the mail ferry. Peak season includes trips to Bailey’s Island, Peaks Island and a moonlight cruise at 9:15 PM.

A different option is to book with the Lucky Catch, a lobster boat. Captain Tom will take you out to haul the traps, hopefully filled with delicious lobsters. It certainly gives you an appetite for them. The trips run five times daily and last 90 minutes.

Higgin's Beach Shop - photo by Kent St. John
Higgin’s Beach Shop – photo by Kent St. John

The Passing of the Portland Head Lighthouse is a bonus. Whale watching and fishing boats also fill the harbor in season.


You need not put on a pair of water wings to enjoy exercising in Portland. Portland Trails is an organization dedicated to organizing and maintaining both hiking and biking trails in the city. Two dozen trails crisscross the area and encompass several parks.

One of the best is the Eastern Promenade that passes through a bluff with good views of the bay and leads to Fort Allen Park. It connects with Baxter Park and its path around the tidal flats.

If beaches and dramatic ocean vistas are more to your liking, Portland has some great options. In nearby Cape Elizabeth is Two Light State Park, no swimming but 40 acres of stunning views complete with two lighthouses.

Past that on route 77 are several beaches that make a dip in the cold waters possible. Crescent Beach State Park is 8 miles from Portland and is over a mile long. My favorite was Higgins Beach in Scarborough.

It has good views and bigger surf. If shopping is your thing then the outlets in nearby Freeport can satisfy and its anchor is the world-renown L.L. Bean store. Any back road will lead to great discoveries.

Print Friendly, PDF & Email

Leave a Reply

Your email address will not be published. Required fields are marked *

Back to Top
Skip to content