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WHY GO: When I first wrote about Portland ME ten years ago, this working port on Casco Bay was a laid-back town with a “mellow vibe.” But now it’s crazy busy, especially in Old Port by the waterfront, where uneven cobblestone streets make ambling a pleasurable challenge.
There are a gazillion places to eat, catering to both the gastronome and tourist trades, and it’s not just the chow. Portland is known for it’s brews as well: Shipyard Brewery and Allagash most notably. But Portland has its cultural side.
The poet, Henry Wadsworth Longfellow was born and raised here, and Winslow Homer had his first exhibition at the Portland Museum of Art – in 1893. There’s so much to do in Portland – here’s how to maximize your time.
Things To Do In Greater Portland, Maine
FOOD TOUR: Maine Foodie Tours. To be sure, foodies have discovered Portland Maine, but this maritime town did not become a culinary destination overnight. Join Maine Foodie Tours three-hour Portland Old Port Culinary Walking Tour for a great historic overview and to explore both the oldest and newest foodstuffs this city offers.
Pam Laskey, founder and owner of Maine Foodie Tours for ten years, runs these stuff-your-face-and-mind expeditions in four Maine towns. Judging from the number of people on my Portland Old Port Walking Tour on a hot early June weekday, these events sell out quickly.
The tour covers a good swath of downtown Portland, and you’ll sample everything from spices and vinegars to lobster mac & cheese, the irresistible Holy Donut, Fish and Chips and Lobster Rolls at Gritty’s (“Maine’s original Brew Pub”), sumptuous soup at Kamasouptra, crab rolls at Mr. Tuna, jams and scones at Stonewall Kitchen, and a singularly Maine confection, the “Needhem” at Dean’s Sweets, made from coconut, dark chocolate, and….mashed Maine Potatoes (though in this case, Maine Potato Vodka).
Along the way, you’ll visit the last remaining authentic Fisherman’s Wharf featuring the iconic Harbor Fish Market that dates back to the late 1800’s, Monument Square, home to the country’s oldest Farmer’s Market, an upscale food hall/chef incubator, and more. Maine Foodie Tours offers a multitude of “Edutainment” opportunities from early morning to late night 21+ tours. The flagship 3-hour Portland Old Port Walking Tour is offered nearly every day year round and costs $69.95 per person.
TOUR: Portland Discovery Tour with Portland Head Lighthouse stop. Traffic is nutty in this city – and so is parking, which is nearly non-existent. And when you do find a place, take it from me, you’ve got to move your car every 2 hours or pay the consequences. Best to hop on a city orientation tour that does not involve your own vehicle, is less than 2 hours, and optimally, has an engaging driver-guide.
You’ll find those requisites with Portland Discovery Land and Sea Tours. Its kiosk is on Long Wharf and Commercial St. next door to Portland Lobster Co. First timers who are also passionate about lighthouses, will want to take the 1 hour 45 minute city and Portland Head Light tour. Yes, it’s a hokey trolley tour, with somewhat jokey and homespun narration. But it covers a lot of ground, especially if you don’t have much time.
Commercial Street is the primary route on the waterfront – a mélange of working and recreational boats, condos, restaurants and bars. Portland Harbor is one of the busiest ports in North America; with a couple of cruise ships sailing in and out of Gateway Terminal daily in season and tankers offloading oil into clusters of oil receptacles – called “tank farms” – that dot the shoreline.
During WWII, 236 Liberty Ships were built right here, mostly by armies of women who collectively came to be known as Rosie the Riveter or Wendy the Welder. The Ferry Terminal is busy with boats going to and from the inhabited islands in Portland Harbor. Over 1,000 people live all year surrounded by water: island kids take the “schoolbus” ferry to the mainland every day.
We lurched by the Maine Maritime Academy Training vessel, which was preparing to shove off to Ireland. You’ll feel as if you can see the Emerald Isle while stopping for a second in a hilltop park overlooking the expansive Casco Bay. From here, you’ll understand why the windmill-like 1807 Portland Observatory (see below), the only remaining signal tower in America, was situated near the top of Congress St. on Munjoy Hill – an Italian and Irish neighborhood with some great eats, like the comfort-food hit, Front Room Restaurant.
Before heading out to the lighthouse (see below) and back to Commercial St., the trolley passes the Neal Dow House – open for tours. By the late 1700’s, over a hundred rum makers operated distilleries in Portland as part of the “Triangle Trade” – tobacco, rum, slaves. Back then, as a rule, sailors had a right to a ration of rum each day, and by the mid-1800’s the general public, including kids, had easy access to the spirit, leading to slovenly disorder all over the city.
Neal Dow, a Quaker and Mayor of Portland, banned the purchase and sale of alcohol in 1851, earning the moniker, “The Father of Prohibition.” Things got ugly, though, when it was discovered that Dow had stored away a goodly amount of demon rum “for medicinal purposes.” For information about the Lighthouse – see below. Trolleys run May-Oct., check website for times, Trolley Tour with Lighthouse Stop, $26 per personVISIT: Fort Williams Park/ Portland Head Lighthouse. The Portland Head Light guides sailors from its perch on a promontory at the entrance to Portland Harbor, and sits at the terminus of a mile long cliff walk within the magnificent waterfront Fort Williams Park. In 1787, President George Washington commissioned the construction of this caisson-style lighthouse, which was completed in 1790 and is now the most photographed lighthouse in America. For good reason. It is breathtaking.TOUR: Wadsworth-Longfellow House. When Henry Wadsworth Longfellow’s younger sister, Anne, passed away in 1901, she left the house and all of its contents – from three generations of Wadsworth-Longfellow’s – to the Maine Historical Society, founded in part by her father, Stephen Longfellow in 1822, stipulating that the Society’s library be built on the property. It was, in 1907, and remains separate from the historic home, which you can now tour.
Henry was born to Stephen Longfellow and Zilpah Wadsworth in his aunt’s home on Fore St. in Portland. (Zilpah’s sister’s husband was away at sea, and she and Stephen were helping her out). A few months later, the Longfellow’s moved, with baby Henry and two year old Stephen, into Zilpah’s parent’s home, had six more children, and raised them all in this three story brick Georgian-style house.
If you’re lucky, you’ll have John Babin, author of Henry Wadsworth Longfellow of Portland, as a tour guide. Far from a dry recounting of the poet’s history, Babin is a storyteller with a fount of knowledge about the man who most famously penned Paul Revere’s Ride. “Come listen my children and you shall hear…” of the antics of one of America’s favorite poets.
Henry wrote his first published piece at the age of 13 – based on a story he heard from his grandfather about a Revolutionary War Battle. He slipped the poem, signed only “Henry,” under the door of the Portland Gazette and it was published in “The Poet’s Corner” – and later slammed for being “remarkably stiff” and “mostly borrowed.” The poet obviously learned from his mistakes.
One of the joys of touring a writer’s home, especially for Lit Lovers like myself, is the thrill of being within reach of objects important to said writer – childhood toys, furniture, writing desks, especially. The rocking horse that Henry loved remains in its original place in the kitchen. The table at which Henry did his homework when he was seven, in the dining room that Stephen converted into his law office, is still there. Even Henry’s boyhood desk, to which he returned again and again even after he moved out, is on display. Henry found inspiration whenever he came home to visit his parents.
Upstairs, a meticulous sampler, embroidered by Zilpah Wadsworth, age 8, in 1786, hangs on the bedroom wall near a rare 1775 armchair desk that belonged to her father, Peleg Wadsworth.Henry graduated High School at 14, went to Bowdoin College and stayed to teach there at 22, and later, after traveling through Europe to study foreign languages, at Harvard. He married twice; his first wife, Mary, died of a miscarriage at 22. (While in mourning, he wrote the poem, The Rainy Day, with the famous line, “Into each life some rain must fall”). He and his second wife, Frances “Fanny,” had five children and grew old together. Henry’s sister, Anne Wadsworth’s, story was a somewhat sadder one. She married George Washington Pierce at 22, and returned home a widow at 25. She never remarried and never had children, choosing instead to take care of her parents, her Aunt Lucia and younger siblings in this home. She always felt the house belonged to the public, and lucky for us, she left it and its intimate garden, in admirable condition. $15, May 1 – May 31: Monday-Sunday 12pm-5pm., June-October: Monday-Saturday 10am-5pm. Sunday: 12pm-5pm.
VISIT: Portland Museum of Art. Winslow Homer first exhibited here in 1893, and since then this human-scale world class museum has focused on American/Maine artists, American and French impressionists, contemporary art, and the decorative arts.
Not only is the art significant inside the multi-faceted PMA, the architecture is as well. Important work from 19th and 20th Century artists adorn the walls of three linked buildings: an 1801 Federalist mansion, a 1911 Beaux-Arts structure and the newest contemporary addition, built in 1983. But the beauty of this museum is that, unlike the monumental art museums in New York or Paris, Portland’s home to great works can be perused in an hour or so, though of course, you may want to linger over your favorite piece. Sat-Wed 10-6, Thurs, Fri 10-8, Free Fri 4-8pm, $15, under 14 free
VISIT: The 1807Portland Observatory. This octagonal, 86′ high tower, the last remaining of its kind in the US, served as a communication station for cargo ships in Portland Harbor. In the early 1800’s, Captain Lemuel Moody manned a powerful telescope through which he could identify incoming vessels from 30 miles away. He’d then signal the dockhands below with coded flags, allowing merchant ships enough time to both reserve a berth on the wharves and to hire a crew of stevedores. In addition to learning about this unique maritime history, the views from the top of the tower are breathtaking. Daily Memorial Day to Columbus Day, 10am-4:30pm; $10 adults, $8 kids
DO: Take a tour of Winslow Homer’s studio at Prouts Neck. Homer was the consummate Maine artist, capturing the essence of maritime and town life in the nation’s most Eastern state. For a limited time in spring and fall, only ten people are allowed at a time to see his preserved studio and inner sanctum. Tickets must be booked through the Portland Museum of Art. Obviously, this sells out in advance- so book quickly. $55 per person seasonally, 207-775- 6148.
DO: Sail on a Windjammer. To get a sense of what the captains of yore must have experienced gliding into pristine Casco Bay, arrange for a two-hour Windjammer sail on either the Baheera or Wendameen – stately tall ships built in the early 1900’s and recently restored. Daily, May – Labor Day; four departures per day, $44 adults, $15 children.
DO: Haul Lobster Traps. Go out with the crew of the Lucky Catch, and get a voucher to take your live Lobster to the Lobster CO on the pier where they’ll boil it up and add side dishes to eat while you watch lobster boats come and go on Casco Bay. The crew of the Lucky Catch discuss sustainable harvesting of Lobster, recount the history of Portland Lighthouse as you motor by, and offer a lot of lobster lore and local history. 90 minutes, May – October; $30 adults, $28 youth, plus wholesale price per pound of lobster if you’d like to take or cook your haul.
STOP IN: Len and Libby Candies, Scarborough. In operation since 1929, Len and Libby Candies made it onto the tourist map when “Lenny” moved in. “Lenny” is a moose formed out 1,700 pounds of fine grade milk chocolate, sculpted in four weeks on site by an art professor from University of Maine and unveiled on July 1, 1997. For almost 20 years, Lenny, standing in a “lake” of white chocolate tinted blue, has not melted or become deformed thanks to the air-conditioning that keeps all candy, including the shop’s signature confection, Bangor Taffy (caramel rolled in powdered sugar), intact.
SNACK/DRINK: Blyth & Burrows. The brand new Blyth & Burrows is a top-shelf gin joint, an up-market speakeasy, a hip spot for bro’s and gf’s of all ages. Josh Miranda, who opened up 14 other bars and restaurants (but never his own) all over the country, wanted to come home and “build the kind of place that Portland hasn’t seen – a cool Portland bar – and I want people to come for that reason.”
Miranda grew up in the Monjoy neighborhood, and as a kid would visit the Eastern Cemetery nearby. There, he was obsessed with the above ground box tombs of two young ship Captains, Captain William Burrows (American), and Samuel Blyth (British), who died in battle during the War of 1812 just off the coast, and were interred side by side. The officer’s portraits, renderings of sailing ships, and other nautical paraphernalia cover the walls in homage to Portland’s maritime history and these men.
But make no mistake. This place is so serious about crafting mixed drinks, you’ll find four eye-catching bars on several levels. Of course, you can get a craft-draft, but opt for a custom-made or snappily-named concoction – such as “I Like the Cut of Your Jib,” ($12) with rye, scotch, pine liqueur, lemon sherbet and sea smoke bitters, or “Death Stalker,” a deadly blend of mescal, tequila, yellow chartreuse, mango, chili, and lime. There’s also a pub menu as befits a funky Maine bar – with Peruvian Ceviche ($11), Lobster Roll ($18), fresh oysters and more, to accompany your liquid refreshments.
And yes, there is an actual speakeasy here – a “secret room” downstairs, accessed either through the bookcase-door, or through the street-level graffiti’d back door flanked by garbage cans. For those who’d like some quiet atmosphere, opt for the more sedate, low-lit Victorian parlor downstairs as well. From the looks of it on a June mid-week night, Miranda’s wish for Blyth & Burrows to be Portland’s new hotspot is coming true.
EAT: A James Beard winning restaurant named Fore St. led the foodie revolution in Portland. But that was so ten years ago. Now, with JB winners left and right, it’s tough to choose. Locals love Eventide, Honey Paw, and Central Provisions for small plates and open kitchen, Front Room Restaurant and Kitchen in the Monjoy Hill neighborhood, for upscale comfort food, Novare Res – considered the “Best Beer Bar in Maine,” and according to Nick Cote, a 22 year old cabin boy at Migis Lodge who has lots of chef friends and “knows almost everything about Foodie Portland”, the Thirsty Pig – for homemade sausages and its Millennial scene. “Downscale” favorites include Otto Pizza, and Empire Chinese Kitchen.
BREAKFAST: Becky’s Diner . Fishermen and locals have been besotted with this hole in the wall for years; you’ll find everything from raved-about blueberry pancakes to twin lobster dinner. Come at 4am when Becky’s opens daily, and you just might find some room amidst the commercial fisherman getting ready to head out for the day’s catch.
SNACK: Holy Donut – made from potatoes, these artisanal donuts take the cake for inventive flavors. No wonder lines are out the door all hours of the day (until 7pm or when the donuts are gone). Duckfat –If your heart can handle it, waddle to hole-in-the-wall Duckfat, 43 Middle St., and order the fries crisped in, yup, duckfat. Save up all of your cholesterol allowances for this one afternoon. It’s worth it.
EAT: Sea Glass Restaurant at Inn By the Sea, Cape Elizabeth. If you choose to bunk at the luxurious, ocean-side Inn By the Sea, you don’t have to go far for some of the best food around. It’s sea-to-table dining in direct view of said Sea, and not only do the chefs know what they are doing (and then some), but wait-staff is bend-over-backwards nice.
Where To Stay In and Near Portland, Maine
STAY: Portland Harbor Hotel. If you want to stay right in town, a block from the docks, and where all the action in – this luxury hotel is the perfect choice. A Maven Favorite – it’s got its own write-up here.
STAY: Inn at Diamond Cove. You’ll have to take a Casco Bay Ferry out to Great Diamond Island (about a 30-45 minute ride), but it’s worth it for this secluded, upscale Inn carved from the remnants of a Naval Training Base. A Maven Favorite – you can read all about it here.
Located off Interstate 95, Portland, Maine is 2 hours from Boston and 5 from NYC by car. It’s also easily accessed by Amtrak train from Boston and other points on the Downeaster route, as well by bus–Concord Bus connect Portland to several New England cities–and by ferry, as Casco Bay Lines provides regular ferry service to nearby islands.