Romantic Things to do in Portland Maine: For Artists, Poets, And Foodies

WHY GO: What are the most Romantic Things to do in Portland Maine? There are plenty, because, well, it’s in New England, on the seacoast, and in Maine. (Nope – this is not the Oregon one).

When I first wrote about this working port on Casco Bay 25 years ago, it was a laid-back town with a “mellow vibe.” But now it’s crazy busy. Especially in Old Port on all the Portland piers by the waterfront, where uneven cobblestone streets make ambling a pleasurable challenge.

Portland ME Old Port Street
Portland ME Old Port Street

There are a gazillion places to eat, catering to both the gastronome and tourist trades. But it’s not just the chow. Portland is known for its brews as well: Shipyard Brewery and Allagash most notably. Portland, however, does have its cultural side, with several must-see historical sites.

Maine Icon on Wheels LLBean Boot
Maine Icon on Wheels LLBean Boot

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. You’ll find many art galleries, and, if you only have a day or two the best bus tour to take.There are so many romantic things to do in Portland – here’s how to maximize your time.

Maine has a world of romantic destinations. Check out our Best Romantic Getaways in Maine roundup.

Romantic Things To Do In Portland Maine

FOOD TOUR: Maine Foodie Tours (Part of Maine Day Ventures)

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.

Harbor Fish Market Portland ME

Pam Laskey, founder and owner of Maine Day Ventures, manages 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.

Grittys Portland ME
Grittys Portland ME

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. Not to mention a singularly Maine confection, the “Needhem” at Dean’s Sweets, made from coconut, dark chocolate, and….mashed Maine Potatoes. (Although in this case, Maine Potato Vodka).

Mr Tuna at the Market Portland ME
Mr Tuna at the Market Portland ME

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 is under the umbrella of Maine Day Ventures, which 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 in season – but check website for times, costs, and availability. 

Portland ME Discovery Tour Bus

TOUR: Portland Discovery Tour with Portland Head Lighthouse stop

If you’re short on time, book a city tour with Portland Discovery Tours. Traffic is nutty in this city – and so is parking, which is nearly non-existent. And when you do find a place, 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 long, and optimally, has an engaging driver-guide.

Long Wharf Portland ME

You’ll find all of those 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 lighthouse fans, 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

As the primary route along the waterfront, Commercial Street features 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.

Cobblestone Old Port Street Portland ME

During WWII, armies of women, collectively  known as “Rosie the Riveter” or “Wendy the Welder,” built 236 Liberty Ships right here. Today, the Ferry Terminal bustles 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.

Munjoy Hill

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. Below us, the Eastern Promenade along the waterfront seemed like a breath of fresh air compared to the goings on in Old Port.

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.

The Father of Prohibition

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 the right to a ration of rum each day. Incredibly, by the mid-1800’s, the general public, including kids, had easy access to the spirit. Growing alcoholism led 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 seasonally. Check website for times  and  prices.Fort Williams Park/ Portland Head Lighthouse.

VISIT: Fort Williams Park/ Portland Head Lighthouse

The Portland Head Light still guides sailors from its perch on a promontory at the entrance to Portland Harbor. It 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. Built in 1790, it’s now the most photographed lighthouse in America. For good reason. It is breathtaking.Wadsworth-Longfellow House Portland ME

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. Anne stipulated that the Society’s library be built on the property. It was, in 1907, and remains separate from the historic home, the Wadsworth-Longfellow House, which you can now tour.

Henry was born to Zilpah Wadsworth and Stephen Longfellow in Stephen’s aunt’s home on Fore St. in Portland.  A few months later, the Longfellow’s moved, with baby Henry and two year old Stephen, into Zilpah’s parent’s home. They had six more children, and raised them all in this three story brick Georgian-style house.

Henry Wadsworth Longfellow portrait

If you’re lucky, John Babin, author of Henry Wadsworth Longfellow of Portland, will be your 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.

Come listen my children and you shall hear

Henry Wadsworth Longfellow writing desk Portland ME

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. Somehow the poem made it into the Gazette’s “Poet’s Corner” – and was later slammed for being “remarkably stiff” and “mostly borrowed.” The poet obviously learned from his mistakes.

Wadsworth-Longfellow childhood rocking horse

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 also still there. Even Henry’s boyhood desk, which he used repeatedly even after he moved out, is on display. Henry found inspiration whenever he came home to visit his parents.

Zilpah Wadsworth hand-sewn sampler

Upstairs, a meticulous sampler, embroidered by Zilpah Wadsworth, age 8, in 1786, hangs on the bedroom wall. It’s mounted near the rare 1775 armchair desk that belonged to her father, Peleg Wadsworth.

Into each life some rain must fall

Henry Wadsworth Longfellow's fathers chair

Henry graduated High School at 14, went to Bowdoin College and stayed to teach there at 22. Years later, after traveling through Europe to study foreign languages, he taught at Harvard. He married twice. Henry’s 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. Anne never remarried and never had children, choosing instead to take care of her parents, her Aunt Lucia, and younger siblings in this home.

Anne Wadsworth always felt the house belonged to the public. Lucky for us, she left it and its beautiful garden, in admirable condition. Check website for hours open, tours, and other programming.

Portland ME Museum of Art

VISIT: Portland Museum of Art

Winslow Homer first exhibited at the Portland Museum of Art in 1893. Since then, this human-scale world class museum has focused on American/Maine artists, American and French impressionists, contemporary art, and the decorative arts.

Maine Art

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 longer. Check website for hours and days open – and admission fees.

1807 Portland Observatory

VISIT: The 1807 Portland Observatory

This octagonal, 86′ high tower is the last remaining of its kind in the US. The Portland Observatory 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.

Moody would 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. Open seasonally – check website for hours and entry fees.

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, up to 12 people at a time are allowed to see Winslow Homer’s preserved studio and inner sanctum. Tickets must be booked through the Portland Museum of Art. Obviously, this sells out in advance- so book quickly. Book online through this Portland Museum website

Windjammer Mural Portland ME

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. These stately tall ships were built in the early 1900’s and have been restored. Seasonal, check website for times and tickets.

Portland Maine Waterfront at dusk
Portland Maine Waterfront at dusk

DO: Watch Lobstermen (and Women) Haul Lobster Traps

Go out with the crew of the Lucky Catch, for an idea of the lobsterman’s life. 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, seasonally, check website for ticket costs. Lobsters also available for purchase.

Lenny at Len and Libbies Candies, Scarborough ME

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,” a 1,700 pound chocolate moose is made of fine grade milk chocolate, sculpted in four weeks on site by an art professor from University of Maine. He was unveiled on July 1, 1997.

Lenny has been standing in a “lake” of white chocolate tinted blue, for over 20 years. Amazingly, he 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.

Restaurants In Portland, MaineBlyth & Burrows Portland ME

SNACK/DRINK: Blyth & Burrows

Blyth & Burrows is a top-shelf gin joint, an up-market speakeasy, a hip spot for bro’s and gf’s of all ages. And, my very favorite cocktail bar in all the land, meaning the whole United States. Josh Miranda, who opened up multiple 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.”

Blyth & Burrows bar Portland ME

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 “Three Sheets,”  or “Mutiny on the Bounty.”

There’s also a pub menu as befits a funky Maine bar – with seafood and other snacks like mussels, fresh oysters and more, to accompany your liquid refreshments.

Blyth & Burrows Speakeasy

Blyth and Burrows speakeasy

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. Growing in popularity over the years, and a date night favorite, Miranda’s wish for Blyth & Burrows to be Portland’s new hotspot has come true.

Becky's Diner Portland ME

BREAKFAST: Becky’s Diner

Fishermen and locals have been besotted with the hole in the wall, Becky’s Diner, since it opened in 1991. 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.

Inside The Holy Donut Portland ME
Inside The Holy Donut Portland ME

SNACK: Holy Donut

Made from potatoes, the artisanal Holy 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).

SNACK: 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.

Sea Glass Restaurant Inn By the Sea

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. Sea Glass, 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.

Central Provisions Portland ME

EAT: Locals Love

James Beard winning restaurant, Fore Street, led the foodie revolution in Portland. But that was so nearly 30 years ago. (Although it still tops many lists). Now, with JB winners left and right, it’s tough to choose. There seems to be a Portland favorite around every corner: a favorite craft beer joint; an award winning fine-dining spot.

Many locals cite Eventide Oyster Co, Honey Paw, and Central Provisions for small plates and open kitchen. Scales and Street & Co. for seafood. The Highroller Lobster for, ya know. And Front Room Restaurant and Kitchen in the Monjoy Hill neighborhood, for upscale comfort food. “Downscale” favorites include OTTO for pizza, and Empire Chinese Kitchen.

Novare Res is considered the “Best Beer Bar in Maine.” Nick Cote, a young old cabin boy at Migis Lodge, who has lots of chef friends and “knows almost everything about Foodie Portland,” favors the Thirsty Pig – for its homemade sausages and Millennial scene.

Where To Stay In and Around Portland Maine

STAY: Portland Harbor Hotel

Portland Harbor Hotel is the perfect choice if you want to stay right in town, on Fore Street a block from the docks, where all the action is. This luxury hotel has been drawing celebrities and people who eschew franchise accommodations since way before Portland was a crazy-trendy destination.

As Portland has grown in culinary prominence, attracting more and more tourists, a slew of other hotels have opened. But the Portland Harbor Hotel has kept up with the times, refashioning formerly traditional rooms into cool nautical-chic spaces, and updating its restaurant’s name and menu.

First Impressions of Portland Harbor Hotel

Hand your car over to the valet in the hotel’s garage, and head up to reception on the 2nd floor.

The ship shape lobby – where you’ll find a small reception desk and the concierge – is dressed in navy blues and corals, with varnished wood floors. It’s quite the departure from the more antique décor that greeted guests prior to the 2017 renovation.

Portland Harbor Hotel Guest room
Guest Room Portland Harbor Hotel ME

Rooms at Portland Harbor Hotel

Now, guest rooms are spacious, bright, colorful and modern, with elements that hark to the Old Port waterfront. Wood floors are burnished to a sheen. Woven maritime signal flags line the wall over each luxury bed. Pictures of old time sailing ships provide some historical perspectives.

Bathrooms are large, with tiled floors, granite sinks, and glass rain showers.

But if your taste runs to Zen contemporary, stay in of the six Executive King Suites, in their own exclusive wing. These rooms feature a two-sided glass fireplace and Japanese sliding doors that open onto a large soaking tub in a khaki-colored granite and wood bathroom.

Turndown service includes a tiny chocolate lobster on your pillow. How more Maine can you get?

Inn by the Sea backyard ocean view Maine

STAY: Inn By The Sea, Cape Elizabeth

Ten minutes from Portland, Inn By the Sea is a Maven Favorite with its own featured write-up.

Higgins Beach Inn

STAY: Higgins Beach Inn, Scarborough

I was having a nice chat with the bartender and a couple of lovely women I’d just met at the Higgins Beach Inn, a boutique hotel 15 minutes from Portland ME. It was 9pm on a Thursday night in June, and all the tables were taken, with more people waiting; ergo, my choice of bar stool. Plus, I was traveling alone and wanted company.

“I hope you don’t write about this place,” said my new friends, sisters who each own a summer bungalow a block away. “We want it for ourselves.” I flashed that smile I use when I can’t make a lasting promise. There’s no way I can keep my mouth shut about this obviously beloved establishment.

Higgins Beach Maine

A block from one of Maine’s most popular sandy shorelines, the Higgins Beach Inn has been a favorite of beachgoers since 1923. Even as it inevitably fell into decline in recent years. Within a residential neighborhood, locals were anxious to see what the new owners – the Migis Group (which also owns 250 Main in Rockland, Migis Lodge on Sebago Lake, and the Blackpoint Inn nearby) – would do with the place when they took it over in 2016. I’m here to report that the refreshed Higgins Beach Inn was, and still is, a wonderful redo – with fresh, modern beachy-clean rooms and an excellent restaurant, Shade.

First Impressions of Higgins Beach Inn

Walk up the steps to the veranda into a small reception area. If it’s dinnertime – the lobby is mobbed with patrons either emerging from or entering the in-house restaurant, Shade. This festive atmosphere is proof of an amazing neighborhood embrace. These customers are not, for the most part, tourists. Many walk here from within a few square blocks.

Rooms at Higgins Beach Inn

Guest Room Higgins Beach Inn

Polished hard wood floors gleam. Contemporary grey and white curtains let in just the right amount of light when closed. (However, there are also black out shades). And the white-duvet clad beds are heavenly.

Though not classically luxurious, the inn is beautiful, clean, breezy, and adorable. I never underestimate the appeal of clean and adorable in refreshed hotel rooms, especially when prices are low compared to other resort hotels.

Dining at Higgins Beach Inn – Shade

Shade Restaurant Higgins Beach Inn ME

Shade is one fun restaurant, with a lively open bar in the middle of the room. There’s an outside deck and a small room where the front veranda used to be. Now enclosed, it’s outfitted with Butcher-block tables rimmed with funky red steel and wood chairs.

In the morning, select from a comfort food breakfast menu – Buttermilk Pancakes, Bagels and Lox, Corned Beef Hash, Cinnamon French Toast – that comes complimentary with the room. By night, Shade turns hip and trendy. But not as crazy-expensive as a resort beach town can be. And the food? Crazy good.

Entrance Inn at Diamond Cove ME
Entrance Inn at Diamond Cove ME

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, passing by Peaks Island – home to the only Umbrella Cover Museum in the world. Yes, you read that correctly). 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 The Inn at Diamond Cove here. 

Getting There:

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 connects Portland to several New England cities. By ferry, Casco Bay Lines provides regular ferry service to nearby islands.


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine,, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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