Portland’s small-town yet urban waterfront

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Glenda C. Booth

Boats dock in Casco Bay along Portland’s waterfront. Portland, the largest city in Maine, dates back to 1632, when it became a British fishing and trading settlement named Casco.
The Greater Portland + Convention Center

From my sixth floor hotel room in the middle of Portland, Maine, I stared at the waters of Casco Bay gently lapping the harbor and was 99 percent convinced I had a blurry sighting of the legendary Casco Bay Sea Serpent porpoising across the bay.

I had just come from the International Cryptozoology Museum, where for two hours I pondered arcane objects and fuzzy images of Bigfoot, Yeti, the Loch Ness Monster and other mysterious creatures.

Roaming around downtown, I had contemplated a snazzy purple chapeau at the Queen of Hats, savored an Eritrean lamb stew at Asmara’s Restaurant, and toured Henry Wadsworth Longfellow’s boyhood home.

Such is Portland, Maine, city of 70,000, a rich mix, pedestrian-friendly, urban center on the water and full of surprises.

You might talk lobster prices with a crusty sea captain at Becky’s lunch counter or world events with a Somalian refugee at a fish market. You might be drawn into analyzing the feats of the Seadogs, Portland’s minor league baseball team, or guessing the essential ingredients of a true whoopee pie.

Forbes magazine labeled Portland one of the country’s most livable cities, which is perhaps why actress Bette Davis had a home on the outskirts.

Kiplinger’s Personal Finance said last year that Portland’s “the best city in the U.S. for Second Acts.”Bon Appetit dubbed it “America’s foodiest small town.” Never mind that Men’s Health listed it “dead last” on their tabulation of 100 hotbeds of sex.


The historic Portland Head Light overlooks the rocky entrance to Portland, Maine’s harbor. The 222-year-old lighthouse is the oldest in Maine.
© L Robinson | Dreamstime.com

Waterfront city

Portland, the largest city in the Pine Tree State and founded in 1632, is known for its working waterfront. It sits on a peninsula jutting into Casco Bay and includes five islands that are part of the city. Mainers, mariners and non, promote the deep harbor that is ice-free year round. (History footnote: Canada had to use Portland for shipping before ice-breakers were invented.)

You can stroll from a Picasso at the Portland Museum of Art to harbor seals near the ferry terminal. Compact, pleasant and easily walkable, Portland offers an urban-small-town-waterfront experience, all in one.

Local resident Sophia Booth, says “It’s impossible to be bored here,” citing events like the First Fridays Art Walk and GreenDrinks, a social networking group focused on environmental concerns. “And where else can you rent a ukulele from the public library?” she asked.

Eclectic tours

A bus or trolley tour (www.PortlandDiscovery.com) is a good starting point for getting to know the city. You’ll roll through stately Victorian neighborhoods and two parks designed by Frederick Law Olmstead that capitalize on scenic water views.

No visit to Maine’s rocky coast is complete without a stop at the 80-foot Portland Headlight and Museum, Maine’s oldest lighthouse dating from 1791 and authorized by President George Washington. When the lighthouse was built, Portland was the closest port to Europe.

Or try the Wicked Walking tour (www.WickedWalkingTours.com) for legends of haunted Portland. On the Culinary Delights (www.mainefoodietours.com) taste tour, you’ll sample local specialties like fiddleheads, seafood chowder (“chowdah”), clams, mussels, whoopee pies and, of course, the king of crustaceans — the Maine lobster.

The Maine Narrow Gauge Railroad (www.mainenarrowgauge.org) has daily summer trips along Casco Bay.

You can while away a day in the Old Port area, especially along Commercial Street, one of the country’s most successfully revitalized warehouse districts. With gulls squalling overhead, ever ready to swoop down and steal morsels, you’ll find around 160 locally-owned shops and no chain retail stores (except one Starbucks that “snuck in”).

Pick up some “moose poop” treats for your pup, or all things blueberry: jam, pancake mix, candy, even barbeque sauce featured on television’s Travel Channel. In the Maine Pantry, you can buy Cajun seasoning mixed in Maine. “Go figure!” says a sign.

Be sure to duck into the no-nonsense Harbor Market for the real coastal Maine, human and piscine, where brawny seafood merchants help eager customers select fish fresh out of the ocean, from eels to haddock. It’s real.

Cultural pursuits

Designed by I.M. Pei, the Portland Museum of Art (www.portlandmuseum.org) has more than 17,000 fine and decorative works of art, including paintings, sculpture, glass and ceramics and furniture dating from the 18th century.

Works by Mainer Andrew Wyeth are favorites, but you can also see art by Rockwell Kent, Louise Nevelson, John Singer Sargent, Edgar Degas, Claude Monet, Edvard Munch and Pierre-Auguste Renoir.

There’s a Winslow Homer collection, and the museum arranges trips to his Prouts Neck studio where he painted many masterpieces.

This summer, the museum will feature an exhibit titled “Shangaa: Art of Tanzania.”

The federal-style Longfellow House was built in 1786 by the poet’s grandfather and was the first brick house in the city.

The Maine Historical Society, the third oldest in the country and dating from 1822, has 15,000 photos and thousands of maps. The Portland Observatory Museum, a National Civil Engineering Landmark that has withstood many fierce storms, is the only remaining historic maritime signal station in the U.S.

The 50-ton Kotzschmar organ in Merrill Auditorium can replicate virtually all the sounds of a symphony orchestra. Built in 1912, it has pipes ranging from the size of a pencil to some 32 feet long, plus 100 miles of wiring that connects the pipes to the keys.

The study of the unknown, the unproven, the anecdotal and the supposed at the International Cryptozoology Museum (http://cryptozoologymuseum.com/) entices. There’s a model of the Feejee Mermaid, which turned out to be a hoax, a monkey sewn to a fish and mummified.

There’s film footage of a big hairy, gorilla-like beast loping through dense vegetation, and “evidence” of more mysterious Maine cryptids beyond the Casco Bay Sea Serpent.

Food and drink

For thirst quenching in a local brewery, tour the Shipyard Brewery Company, a microbrewery that flies a beer keg on the roof instead of a flag.

It’s hard not to eat well in Portland. DeMillos on the harbor is a floating former car ferry loaded with nautical imagery where “diners are passengers.” Fresh lobsters, mussels and clams practically jump off the menu. “The clams you eat here today slept last night in Casco Bay,” the restaurant touts.

J’s Oyster Bar on the waterfront is always crowded but worth the wait for oysters “raw and nude.” J’s makes chowders, lobster rolls and a scallop casserole to die for.

Family-owned, downhome Becky’s Diner has whole-belly fried clams, clam cakes, homemade soups and freshly-made pies. A waitress told me the banana cream pie “weighs 20 pounds.” A regular customer commented, “The food is consistently good, and the waitresses are sweet.”

If you really want a fresh lobster, catch one. Sail out with Lucky Catch Lobstering (www.luckycatch.com) and haul traps. You’ll learn all about hardshells, softshells, shedders, shorts, culls and keepers. The Portland Lobster Company restaurant on the pier will cook them for you. Prepare for drippy elbows.

Island hopping

After traipsing around the city, relaxing on Great Chebeague Island is a refreshing respite. In 2006, Chebeaguers voted to secede from the town of Cumberland, and they carefully nurture a year-round community esprit de corps.

“We don’t want to be a snooty, touristy Nantucket-type island,” the town historian told me, so they killed the construction of a bridge to the mainland.

The island is four miles long and 1.5 miles wide, and the speed limit is 30 mph all over. There’s one grocery and one restaurant, sort of.

Historically known for stone sloops, boats that carried granite from quarries, Chebeague has 350 year-round residents. Proud islanders view Casco Bay as “the moat.” It separates and protects them from the city.

While Chebeaguers eschew the touristy, locals are welcoming. Everyone waves to you.

I arrived at the dock with a suitcase and no arrangements for transportation to the Chebeague Inn. As I watched my suitcase hoisted up and down by a crane, I befriended a woman waiting for her groceries to come off the ferry. When I asked how to get to the inn, she offered me a ride in her rusty 1970s Ford station wagon with floor “ventilation.”

The Chebeague Island Inn (www .chebeagueislandinn.com), dubbed the “11th Best Small Hotel in the U.S.” by CondéNast Traveler, is a restored, Greek Revival-style 1920s hotel with wide relaxing porches and sweeping water views. From a comfy wicker chair, you can watch terns dive and great blue herons fish. If you need to move around, poke around in the tide pools. Rooms start at $166 per night, including breakfast.

Casco Bay Lines (www.CascoBayLines.com) makes frequent daily trips from the ferry terminal to six Casco Bay islands. You can cruise around and absorb the scenery, day trip, or stop at one for a stay.

For downtown lodging, the Hilton Garden Inn and Holiday Inn by the Bay are the most reasonably priced hotels.

 U.S. Airways has July flights from Reagan National (nonstop) for $199. United has a flight from BWI through Cleveland for $199. You can tour much of the city over several days without a car, but you need a car to venture beyond downtown.

For more information, visit the Greater Portland Convention and Visitors Bureau, www.visitportland.com, and the Maine Office of Tourism, www.mainetourism.com.

Glenda C. Booth is a travel writer based in Alexandria, Va.