Best Things to Do in Portland, Maine

For a city of such modest size — just under 70,000 residents call it home — Portland packs plenty of appeal. History, food, art, and of course the seaside location make this city one of New England’s bucket-list destinations. Here is a city of contrasts: Boutique shops bump up against Portland’s still-working harbor; down-home cooking draws foodies and so does haute cuisine. Put another way, Portland’s identities are many, which makes it a perfect landing spot for any kind of traveler. Ready to explore? Read on for our guide to the best things to do in Portland, Maine.

The Very Best Things to Do in Portland, Maine

PORTLAND FARMERS’ MARKET

From late April to late November, the Saturday morning market, based in Deering Oaks Park, celebrates everything that can be grown, raised, tended, or fermented for nearly a hundred miles around. Portland chefs are buying from these same agricultural specialists, scooping up ingredients such as wild mushrooms from North Spore and yogurt and fresh cheeses from Swallowtail Farm—which means that your market visit will also tell you what’s really in season on a restaurant’s menu. A 2018 Yankee Editors’ Pick for “Best Farmers’ Market.”

LUCKY CATCH LOBSTER TOUR

Cruise Casco Bay aboard the Lucky Catch, and in addition to learning all about lobsters, you can help haul, bait, and set traps — and perhaps even catch your dinner.

LONGFELLOW BOOKS

Pick up the latest best-seller or choose from staff recommendations; peruse the extensive mix of new and used books; attend an author reading; join a book group; snuggle with the store cat — it’s all possible at this thriving, fiercely independent downtown Portland bookstore staffed by passionate readers. Named a 2017 Yankee Editors’ Pick for “Best Bookstore.” 

VICTORIA MANSION

Widely considered the most magnificently ornamented dwelling of its period remaining in the country, the mid-19th-century Victoria Mansion retains about 90 percent of designer Gustave Herter’s original furnishings. Jaw-droppers include a 6-by-25-foot stained-glass ceiling window, mind-boggling trompe l’oeil wall and ceiling flourishes, and the dizzying colors and patterns of the Turkish Smoking Room. Named a 2016 Yankee Editors’ Pick for “Best Historic House Museum.”

PORTLAND HEAD LIGHT

In Fort Williams Park, just four miles from downtown Portland, Maine’s oldest lighthouse (commissioned by George Washington, no less) guards the harbor. Visit the museum in the keeper’s house and picnic in the park. Named a 2016 Yankee Editors’ Pick for “Best Iconic State Attraction.”

PORTLAND SCHOONER COMPANY

Let daylight fade to night while cruising by lighthouses, forts, and islands on a two-hour sail aboard the historic windjammers Bagheera and Wendameen, both elegant ocean schooners built in East Boothbay.

PORTLAND MUSEUM OF ART

Explore three centuries of works, including a top-flight collection of paintings by American realist and impressionist masters (Rockwell Kent, Andrew Wyeth, and Marsden Hartley, to name a few) and fine and decorative arts. Named a 2015 Yankee Editors’ Pick for “Best Historic Highlight: Art & Architecture.”

ALLAGASH BREWERY

Belgian-inspired beers are on the menu at Allagash, launched in 1995 by owner Rob Tod using jury-rigged dairy equipment inherited from Vermont ice cream legends Ben Cohen and Jerry Greenfield. Beer pours and tours are offered regularly.

Where to Stay in Portland, Maine

BLIND TIGER

Comprising a pair of thoroughly renovated 19th-century homes, Blind Tiger Portland is a Lark Hotel located right in the heart of Portland’s West End, giving you easy walking access to the city’s best food, music, art and shopping… assuming you can pull yourself away from your luxurious quarters.

THE INN AT DIAMOND COVE

You and your significant other can leave both car and cares on the mainland when you hop a Casco Bay Ferry to Great Diamond Island, where bicycles and electric golf carts are the chief alternatives to walking. An inspired redeployment of the former barracks of the 1890s Fort McKinley, the 44-room Inn at Diamond Cove offers a plush and tranquil retreat. To up the intimacy factor, ask for a parlor suite with fireplace for snuggling on a cool night, and reserve a waterfront table at the inn’s sister restaurant, Diamond’s Edge. A 2018 Yankee Editors’ Pick for “Best Romantic Getaway.”

INN AT PARK SPRING

The tastefully updated Inn at Park Spring occupies an 1835 brick townhouse in Portland’s upscale West End neighborhood, putting guests within easy walking distance of the sights, shops, and restaurants of downtown and the arts district. The guest rooms and public spaces are decorated with restraint (nothing froufrou here), and attentive innkeepers pamper guests with hearty breakfasts and afternoon treats.

THE PRESS HOTEL

Once the offices of Maine’s largest newspaper, the Portland Press Herald, the seven-story Gannett Building in downtown Portland is now home to a Marriott Autograph Collection property that any journalist or lover of print would be delighted to call home. Vintage typewriters dangle from one wall of the lobby, while behind the registration desk you’ll find blocks of letterpress type. Newsprint touches continue along the hallway to your room, where walls are covered with actual headlines, such as “Elderly Lobster Set Free.” Across from City Hall, the 110-room hotel is close to all the restaurants, bars, and shops in town.

For more on where to stay in Portland, check out our guide to the city’s best hotels.

Where to Eat in Portland, Maine

NOSH

No one here would bat an eye if you just opted for a basic cheeseburger (albeit fancied up on a brioche bun). But since this Portland hot spot excels at piling it on creatively, why not get in on the adventure? Beginning with beef from grass-fed, grain-finished cows, Nosh serves up more than half a dozen memorable specialty burgers, including the coma-inducing Apocalypse Now: one to four patties laden with American cheese, crisp pork belly, smoked bacon, and foie gras pâté and topped with cherry jam. Named a 2017 Yankee Editors’ Pick for “Best Burger.” 

THE HOLY DONUT

Potato doughnuts are not native to Maine — the first printed recipes appeared during the Great Depression as a way to substitute cheap spuds for pricier flour — but they became a staple food in Maine potato country. All 20-odd flavors at this Portland icon use Maine-grown potatoes in the dough, producing a dunker so light and moist you’ll wonder why anyone makes doughnuts without them. (We even named the chocolate sea salt doughnut here one of the Best Comfort Foods in New England in the January/February 2018 issue of Yankee.)

EVENTIDE OYSTER CO.

The bar’s huge block of granite and ice topped with oysters signals you’ve come to the right place. Eventide made the old-fashioned oyster bar cool again by offering at least a dozen varieties—mostly from Maine but a few from “away”—on the half shell along with a sassy cocktail program. (The Dirty Dirty Martini pairs the booze with olive brine, oyster brine, and hot sauce.) The fried fish is often hake, an underutilized species this side of the Atlantic but a Parisian favorite. We love the Eventide lobster roll, too. A 2018 Yankee Editors’ Pick for “Best Oyster Bar.”

MIYAKE

James Beard Award–nominated chef Masa Miyake takes Japanese cuisine to a new level, using ultrafresh ingredients (some sourced from his own farm) and employing Japanese, Italian, and French techniques. While you can’t go wrong ordering from the à la carte options, you should splurge at least once on the omakase, or chef’s tasting menu, for a dining adventure.  Named a 2017 Yankee Editors’ Pick for “Best Sushi.” 

For more on where to eat in Portland, check out our dining guide to the city’s best restaurants.

What are your favorite things to do in Portland, Maine? Let us know!

This post was first published in 2018 and has been updated.

SEE MORE:
The Most Beautiful Places in Maine
The Great Maine Lobster Roll Adventure
Acadia National Park | Things to Do & See

Ian Aldrich

Ian Aldrich is the executive editor at Yankee, where he has worked for more for two decades. As the magazine’s staff feature writer, he writes stories that delve deep into issues facing communities throughout New England. In 2019 he received gold in the reporting category at the annual City-Regional Magazine conference for his story on New England’s opioid crisis. Ian’s work has been recognized by both the Best American Sports and Best American Travel Writing anthologies. He lives with his family in Dublin, New Hampshire.

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