Wednesday, February 4, 2026

An Insider’s Information to Portland, Maine

High 5 Can’t Miss

  • E-book a keep at The Docent’s Assortment and cook dinner with a few of Maine’s regionally sourced produce and seafood.
  • Catch a Sea Canine sport at Hadlock Area. 
  • Head to Eventide for the can’t-miss brown butter lobster roll and a spherical of oysters. 
  • Carve out a while to browse Washington Avenue for every thing from ferment-forward pantry staples to classic cookbooks.
  • Stroll on the Japanese Promenade to work up an urge for food and soak up views of Casco Bay.

I first began visiting Portland often slightly over 10 years in the past, taking the fast journey north from Boston each spare weekend I may. Nicely thought to be a culinary scorching spot that’s soaked in seaside allure, the simply walkable metropolis is the right place to spend an extended weekend—or extra. From the cobblestone streets of the Outdated Port to beloved native haunts on Washington Avenue and the West Finish, it’s simple to really feel at house right here immediately, whereas nonetheless typically experiencing it like a vacationer.

Finest Accommodations & Resorts

Visitor room inside The Blind Tiger resort.

Lark Accommodations


Longfellow Lodge

Longfellow Lodge is just not solely located within the coronary heart of one in every of Portland’s greatest neighborhoods, the West Finish, but it surely’s additionally comparatively massive by the town’s requirements. In case you want another excuse to e book, although, the property is only a stone’s throw from Tandem Espresso + Bakery, placing you at a definite benefit to be first in line for one in every of their legendary breakfast sandwiches. The 48-room boutique resort has a give attention to wellness, housing an on-site spa with non-public infrared saunas and visitor rooms designed for an excellent evening’s relaxation.

The Francis

The Francis is a small boutique property from the identical staff behind the Longfellow Lodge, Unusual Hospitality. It’s housed in a constructing from 1881, and every of the 15 rooms has its personal distinctive allure. Like all historic properties, it has some quirks. Whereas the free parking and included breakfast are massive perks, one of many resort’s greatest options is that it shares a constructing with Wayside Tavern, a high restaurant within the metropolis. Finn Naylor, advertising director at Rosemont Market & Bakery, says, “Wayside Tavern is on the high of my listing. Their meals is all the time seasonal and considerate, the wine listing is superb, and the vibe is unfussy in the easiest way.”

The Docent’s Assortment

In case you’ve ever wished to strive residing in one in every of downtown Portland’s greatest neighborhoods, the Outdated Port, that is the place to do it. The Docent’s Assortment provides a handful of loft-style residences, full with kitchens. Jordan Nugent, director of journey and occasions with Expertise Maine, says, “I like The Docent’s Assortment as a result of it feels extra like residences, every with its personal kitchen and residing space, positioned within the coronary heart of the Outdated Port. It’s nice for bigger teams touring collectively or longer stays.”

Blind Tiger

Blind Tiger is made up of two historic buildings in Portland’s West Finish. When touring all through New England, I all the time exit of my option to see if there’s a Lark Accommodations property close by. No two rooms are ever an identical and every location is engrained in its particular person neighborhood, with Blind Tiger being no totally different. The property provides a complimentary mild breakfast, and free parking and ample (and comfy) public house on the primary flooring make it simple to linger between jaunts to one of many many wonderful eating places and bakeries within the neighborhood.

Press Lodge

The Press Lodge is in downtown Portland, working within the historic headquarters of the Portland Press Herald. The 110-room property, operated by Marriott, has a boutique really feel and welcome facilities equivalent to valet parking and room service. Don’t skip out on breakfast at Union, the place you’ll ponder the place blueberry breakfast sausage has been all of your life.

Finest Issues to Do

Boats docked in Portland’s harbor.

Ivey Redding/Journey + Leisure


Go to Fort Williams Park.

Take a fast drive over to Cape Elizabeth and stroll by means of Fort Williams Park. Roughly quarter-hour from downtown Portland, the park spans greater than 90 acres, with dramatic cliffs and the enduring Portland Head Gentle. Pack a picnic lunch or seize one of many metropolis’s greatest lobster rolls from Chunk Into Maine.

Get on the water.

The easiest way to understand the fantastic thing about Portland is to see it from the water, and by chance, there’s no scarcity of how to do it. Nugent says, “Get out on the water when the climate is good. We now have a lot entry to neighboring islands and boat excursions.” You’ll be able to take pleasure in a wine tasting aboard a sailboat with Wine Sensible Wine Sails, see how lobsters are caught with Fortunate Catch, hop on a low-key sundown lighthouse tour with Portland Schooner Co., or take an informal cruise onboard the mail boat. In keeping with Naylor, “In case you haven’t taken a sundown cruise on Casco Bay Traces, add it to your listing. It’s the very best midweek reset—inexpensive, BYO every thing, and completely magical. My transfer? Cease by Rosemont beforehand for a relaxing bottle of rosé, a recent baguette, and a few charcuterie, then hop on the ferry and let the ocean do the remaining.”

Catch a sport at Hadlock Area.

If you end up in Portland throughout baseball season, don’t miss the chance to catch a Sea Canine sport. Hadlock Area is a fast drive from downtown, and the vitality right here is unparalleled. Nothing feels fairly like summer time in Maine than watching a sport on a sun-drenched afternoon with a Sea Canine Biscuit ice cream sandwich in hand.

Head to the seaside.

There’s nothing like packing up a cooler filled with snacks and spending a few hours by the shore. Cease by Mr. Tuna for a bento field, Ramona’s for a hoagie, or Rosemont Market & Bakery to construct your personal snack platter earlier than heading to Willard Seaside in South Portland, Crescent Seaside in South Portland, and native’s favourite Ferry Seaside in Scarborough. Naylor says, “I’m a giant believer within the seaside being a year-round exercise. My mates and I are at Kettle Cove most Saturday mornings in January, breakfast burritos in hand. The proximity to seashores is a part of what makes Portland so particular—quarter-hour in any route and also you’re there.”

Cease by a brewery.

If there’s one factor Maine does properly, it’s craft beer. With greater than 100 breweries within the state, you’re almost assured to search out your favourite type round Portland. In case you’re a beer fanatic, it’s price carving out a while to spend a couple of hours hopping between some breweries. Oxbow, Allagash Brewing Firm, Bissell Brothers, and Bunker Brewing Co. are all native favorites.

Finest Eating places

Quite a lot of oysters on ice.

Eventide


Crispy Gai

Crispy Gai will make you rethink your total night every time you end up in its orbit, abruptly scanning the block for a parking spot to sneak in a fast go to. Between its stellar bar program with authentic takes on tiki-style classics and crave-worthy wings dusted with spices you’ll be dreaming of for weeks, Crispy Gai is an absolute must-visit.

Magissa

Magissa is a Greek-style taverna in East Bayside that’s owned and operated by the staff who was behind The Greeks of Peaks meals truck. The menu options small bites, meze, and shareable dishes which are precisely what you’ll want after spending a day hopping from breweries, seashores, or each. The meals and cocktails are artistic, expertly executed, and made with care.

Eventide

It’s unattainable to speak about Portland with out mentioning Eventide. Its brown butter lobster roll—made with heat lobster meat and piled excessive on a pillowy tender bao bun—and flights of oysters from right here and away make vying for a parking spot and going through the ever-present waitlist greater than price it.

Scales

If visiting Portland has you conjuring up visions of feasting on recent fish whereas gazing out throughout the docks in Outdated Port, Scales is the place for you. The restaurant is barely upscale, with out being fussy, and a part of a powerhouse group that operates Avenue & Co., Fore Avenue, and Commonplace Baking Co.. Don’t miss the cloverleaf rolls, halibut with brown butter and hazelnuts, and regardless of the custard of the day is.

Twelve

Nestled on Thames Avenue, Twelve is doing one thing actually particular. The back and front of the home are armed with stellar resumes—and it reveals. The staff at Twelve places their spin on basic Maine dishes and components, (suppose: a martini crafted with kombu). Cease by for a cocktail, order dishes a la carte, or go all in on the prix fixe, however no matter you do, don’t miss out on the lobster roll served on a flaky croissant.

Finest Time to Go to

Folks strolling round Portland’s Wharf space.

Ivey Redding/Journey + Leisure


If finances isn’t a consideration, you’ll be hard-pressed to discover a higher time to go to Maine than late June by means of mid-September. In fact, you received’t be the one one with this concept, so be ready to pay a premium for lodging and e book your reservations properly forward of time. In case you’re prepared to commerce in a far much less crowded metropolis for some cooler temperatures, think about planning a go to throughout late Spring (April-Could) or early fall (late September-October). The climate will nonetheless be gentle, however the uptick in guests throughout excessive season is stark and the town could also be far more pleasurable within the shoulder seasons.

How you can Get There

In case you’re fortunate, you may catch a direct flight into Portland Worldwide Jetport (PWM), which is simply quarter-hour from downtown Portland. In any other case, fly into Boston’s Logan Worldwide Airport and both lease a automobile to drive the roughly two hours north to Portland, take a bus by way of Harmony Coach, or hop on the Amtrak Downeaster for the roughly 2.5-hour journey. Each function year-round.

Neighborhoods to Go to

Buildings in Portland’s outdated historic neighborhood.

Tamme Wichmann/Adobe Inventory


Washington Avenue

Whereas guests could flock to the Outdated Port, Washington Avenue is the place you’ll discover locals on their days and nights off. Make sure you carve out a few hours to discover the bars, eating places, and retailers on Washington Avenue. Cease by Maine & Loire for a bottle of wine (or two) to convey again to your resort, peruse Onggi for some ferment-forward pantry staples, snag some snacks from Sissle & Daughters, and flick through uncommon and classic cookbooks at Rabelais.

Japanese Promenade

Since there’s a lot nice meals in Portland, you’re going to wish a spot to work up an urge for food earlier than your subsequent meal. Enter: the Japanese Promenade. The 78-acre park encompasses a two-mile harborside stroll that has sweeping views of Casco Bay and the Portland harbor, plus loads of benches and inexperienced house for those who simply want a spot with nice views to chill out. Naylor says, “I like strolling down the Japanese Promenade Path—it drops you proper onto Industrial Avenue, which is ideal for slightly procuring, restaurant hopping, or simply watching the working waterfront in motion.”

South Portland

Simply throughout the bridge from the Outdated Port is South Portland, house to stellar seashores and a few standout meals. Don’t miss Night time Strikes Bread, SoPo Seafood, and Purple’s Dairy Freeze—all supreme stops earlier than or after a stroll on Willard Seaside.

Outdated Port

House to the working waterfront and memento retailers galore, the Outdated Port is a well-liked space within the metropolis. Whereas there are vacationer traps right here, some gems do exist on this a part of city, too. Room for Enchancment is a comfy dive bar serving up enjoyable takes on basic cocktails and snacks just like the Purple Snapper, Maine’s illustrious neon-red scorching canines. In case your lodging have a kitchen, you’ll want to go to Harbor Fish Market, the place you’ll discover Maine lobsters, clams, mussels, and extra. Seize a lobster roll at Luke’s Lobster and prepare—the staff might be reopening Portland’s legendary Dry Dock restaurant later this summer time with chef Matt Ginn on the helm.

How you can Get Round

Automobiles driving previous pedestrians in Portland, Maine.

Ivey Redding/Journey + Leisure


Portland is a walkable metropolis, however if you wish to enterprise outdoors of downtown to go to close by seashores, you’ll need to have a automobile. Journey-share providers are pretty accessible and inexpensive, however wait occasions may be longer throughout off-peak journey occasions. You’ll be able to take the Amtrak Downeaster to close by cities up the coast as properly. There are rental automobile firms primarily based at Portland Worldwide Jetport, however you’ll want to e book upfront for those who’re visiting through the summer time or different busy occasions all year long, as leases can hit capability rapidly.

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