Skip to main content

Portland, Maine: A Big Little City


Where Gumbo Was #185

Whenever I tell friends I’m off to visit Portland, for some reason they assume 20160920_183345_002I’m going to Oregon, home of what I think of as “the other Portland.”

Both cities are foodie towns, both have reputations for “hip” and both are vacation destin-ations. Without having been to Oregon yet, I do believe the similarities end there.

And I’m clearly not the only one who knows the difference, because, in order, GarryRF, George G, PortMoresby and Jonathan L, recognized one of my favorite destinations for a long weekend or a longer short break. It’s got history, water, a scenic area around it, and possibly more restaurants per capita than anywhere else: 230 restaurants and a population of only around 66,000.

Portland's City Hall

Portland often seems bigger than that, at least in part because it’s the anchor for a metro area of nearly half a million—over a third of Maine’s population. Although the city has spread out over the years, and includes several of the islands that dot Casco Bay, the heart of the city is still the “Peninsula,” which includes the areas most visited by tourists: the Old Port, and the Arts District above it.

The historic Customs House; Portland was a major port for many years.

Portland got its start in the early 17th century as a village called Casco. As time went on, and after fires and battles with both Indians and French forces, it became first Falmouth, and then Portland, named for the island in Dorset, England. And yes, Portland, Oregon is named for Portland, Maine, not for England. It was the first capital when Maine became a state in 1820.


One thing you notice right away in Portland: brick and masonry. Wooden buildings are a rarity. After the last of Portland’s great fires (the city’s motto is Resurgam, Latin for I Rise Again), new laws required masonry construction. The fire, on July 4, 1866, started from Independence Day fireworks, and destroyed the entire waterfront area of the city, leaving 10,000 homeless, and living in tents for months.


Portland has some other surprises. It has one of only two remaining municipal organs in the U.S., the only remaining maritime signal tower (the Portland Observatory), an operating narrow-gauge railroad and museum, a commuter and freight ferry system that serves a dozen or so islands in Casco Bay, the home of Henry Wadsworth Longfellow, and an art museum that would not be out of place in a city several times its size.

20160920_191227Not only a rarity as a municipal organ, the Kotschmar Organ in City Hall is one of the world's fifteen largest. A concert was one of our visit highlights.

It’s a serious East Coast output of hip coffee culture. At Arabica, one of Portland's oldest proponents of the Seattle-based coffee revolution, we even got a coffee lesson, along with seriously good coffee.


With all those eateries, there are dozens of the kind that pop up in all the serious food magazines, and we've enjoyed them. But one of our favorites, hands down, is what may just be the world’s best diner: Becky’s, on the business end of the waterfront. Busy at all hours, with great breakfast items, great seafood, great (home-made) baked goods, and possibly the only place around that has two kinds of corned beef hash—home-made, and canned—on the menu. Skip the canned!

Photo: John Phelan/Wikimedia

Another favorite has an odd name—Duck Fat—but it’s actually just a description. Its specialty is wonderful fries, cooked in duck fat. Fabulous milkshakes as well, great sandwiches, and plenty of napkins. You’ll need them. Here’s their version of poutine, made with duck gravy.


 I find it hard to pass up a good bakery, especially one focused on bread. Pie and donuts come second in my world. Portland has two that I keep heading back to, one for each taste. For great breads of quite a few varieties, there's the Standard Baking Company, shown here. The upstairs windows belong to Fore Street, the first of Portland's restaurants to achieve big-name status.


Standard is right on the waterfront; a couple of blocks up is Two Fat Cats (which actually had two fat cats when we first went there 10 years ago). You can see an assortment of what keeps us coming back. There's also a really good whoopie pie. I have a fondness for the bumbleberry (blueberry, blackberry, rhubarb and apple, but this year's winner was a drunken cherry pie.


Here's another great idea: Pick up pizza from Micuci's Grocery, a surviving remnant of Portland's urban-renewed-in-the-70s Little Italy, and carry it to the Sea Dog Brewery's tasting room. It's the best soft-crust Sicilian-style pizza I can remember (although I'm a fan of the tougher New York Sicilian). Pair it with a flight of beer and ale samples (or unusual soft drinks). We were on a food tour, and it was one of the highlights...although choosing four beers from a list of 18 wasn't easy!


Leaving town for a 20-minute ride to Cape Elizabeth, with its two lighthouses, brought us back to the Lobster Shack. No other name. Lobsters. Clams. Scallops. Fish. Fries. Onion Rings. Mostly fried. Some of the lobster eaters were a bit disappointed this time, but in other years it was some of the best. I had the fried scallops, and they were just about perfect. Popular enough that you sometimes have to line up to put in your order...


And a reminder who NOT to share your meal with!

DSC00631DSC0063320160920_093727Near City Hall, a statue honors the area's lobstermen.

Not all the food in Portland is in restaurants; there's an active Wednesday morning market filled with tasty produce and more. This is just a sample.


Portland has become a major cruise ship stop, with one or two ships in port nearly every day. With all those passengers coming ashore, there's a thriving market for crafts and more just outside the ocean terminal.


But we saved our cruising for a more local version. Casco Bay Lines, the public ferry system that serves the inhabited islands in the Portland area. In addition to regular passenger service, there are car services to some of the islands, and there's the mailboat. We chose the mailboat, which makes two daily trips on a route serving five of the eight islands, and gets to the others on an as-need basis. Below, our view as we left the harbor.

DSC00557The mailboat uses a special ship with cargo spaces as well as passenger seats; its rooftop crane lifts skids of food, water, construction materials, appliances, whatever is needed on the islands, including Amazon packages.


Of course, there's plenty to see on land, as well, although we didn't take this tour, which uses a retired fire truck as a tour bus.


We encountered it along the Eastern Promenade, which combines a historic neighborhood with a large park along the end of the peninsula. It was from here that Portland residents were able to look out over the bay in June 1863 and see parts of the northernmost naval battle of the Civil War. 

DSC00641Confederate raiders had entered the bay and seized two ships, including a Coast Guard cutter; they hoped to destroy shipping. However, they were forced to flee and were pursued by locals in excursion steamers. Eventually the Confederates were forced to abandon ship and surrender to Portland's mayor.


The raid was not Portland's only connection with the Civil War and the events leading up to it; a number of local citizens were active participants in the Underground Railroad. Among them were both whites and free black citizens. Their trades included barbers and used clothing merchants; they were able to help not only change appearances and provide clothing, but also to ship clothing south with Abolitionist pamphlets sewn into the seams. There are markers like this in many spots around town.


And here's another of Portland's special sites: the Portland Observatory. It's not a light house, nor an astronomical observatory. It was built in 1807 by a retired sea captain named Moody. Capt. Moody used the tower and a powerful telescope to spot ships hours before they entered the bay. Owners paid Moody $5 a year service to post flags notifying them of flag messages from the ships. The service continued until two-way radio made it obsolete in the 1920s. It's open to visitors...or to visitors who want to climb 7 flights of stairs.


So...Portland, a great little city to visit!


Images (33)
  • 20160919_185834
  • 20160920_093727
  • 20160920_183345_002
  • 20160920_191227
  • 20160921_090119
  • 20160922_125638
  • 28064424-28064424
  • DSC00514
  • DSC00515
  • DSC00522
  • DSC00529
  • DSC00532
  • DSC00543
  • DSC00544
  • DSC00545
  • DSC00546
  • DSC00547
  • DSC00557
  • DSC00562
  • DSC00569
  • DSC00630
  • DSC00631
  • DSC00633
  • DSC00639
  • DSC00641
  • DSC00644
  • DSC00646
  • DSC00654
  • DSC00657
  • DSC00660
  • Ruins_of_the_Great_Fire_at_Portland,_ME
  • IMG_1440
  • DSC00590

The best part of every trip is realizing that it has upset your expectations

Add Comment

Comments (4)

Newest · Oldest · Popular

It's about 30 miles north of Cabot's Cove, which is near Wells, Maine. Which is at one end of the excellent Rachel Carson National Wildlife Refuge, which combines forest and shore habitats and makes a wonderful walk. 

It was featured in a couple of Pictures of the Day, and was the scene, back in 2013, of Where in the World is TravelGumbo #5

The best part of every trip is realizing that it has upset your expectations

Thanks, SeeSaw! We didn't get to 'OOB' this trip, but we were there a few years ago, and it was just about as good a combination of quaint, hip and tacky as you could wish for...

The best part of every trip is realizing that it has upset your expectations

Link copied to your clipboard.