Long weekend in Portland, Maine

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Named one of the country’s most livable cities by Forbes, Portland offers breezy bay living, a tranquil harbor front and historic homes on cobblestone streets. Here’s your Portland, Maine long weekend itinerary.

Named one of the country’s most livable cities by Forbes, Portland offers breezy bay living, a tranquil harbor front and historic homes on cobblestone streets. There’s no doubt lobster is one of Portland’s claims to fame, but on a long weekend in the city, you’ll discover there’s more to Portland than good seafood (but rest assured, there’s plenty of that to go around, too).


While there are plenty of hotel choices in Portland, it’s the quaint bed and breakfasts that steal the lodging spotlight.

Pomegranate Inn (Image: Dana Moos)
Pomegranate Inn (Image: Dana Moos)

The boutique Pomegranate Inn offers playful decor in an eclectic yet elegant setting. Tea and cookies upon arrival, artisan breakfasts and gas fireplaces add to the charming experience at this B&B, a 10-minute walk from the downtown district of Congress Street.

Another noteworthy inn is The Chadwick, a cozy stay in a restored Victorian home in the historic West End neighborhood. This quiet B&B offers romantic rooms and gourmet breakfasts using local ingredients, including paprika potatoes and Maine lobster eggs benedict.


Yes, there’s more to dining in Portland than lobster shacks and beer. But so many locals do both so well, and these Portland staples make for a great starting point.

If you’re headed into Cape Elizabeth to see the lighthouses or state parks, stop by the Bite Into Maine food truck for one of the state’s best lobster rolls. If you’re looking for something a little fancier than a lobster shack, the lobster diavolo at Street and Co. in Old Port is calling your name.

Beer flight at Great Lost Bear (Image: Bernt Rostad)
Beer flight at Great Lost Bear (Image: Bernt Rostad)

During your long weekend, stop in at a neighborhood pub for small-batch, handcrafted brews. One Portland favorite is Great Lost Bear, where pub fare like burgers and cheesesteaks are easily washed down with a glass of one of the dozens of local craft beers on tap. Can’t decide which beer to choose? The beer flight lets you sample a few of Portland’s best brews.

Another local institution? Duckfat, a sandwich shop where the potatoes are fried in – you guessed it – duck fat. Go the extra mile and order the poutine, where the fries are covered in duck gravy, cheese curds and a fried duck egg.


Portland Head Lighthouse (Image: Bernt Rostad)
Portland Head Lighthouse (Image: Bernt Rostad)

A trip south to Cape Elizabeth is well worth the photo opportunities at Portland Head Lighthouse and Fort Williams State Park. In town, breweries like Allagash and Shipyard offer tours and tastings of specialty beers, ales and stouts.

If breweries aren’t your thing, head to the perfectly preserved Old Port district, where you can take in historic architecture as you explore the cobblestone streets. Plenty of boutique shops will vie for your attention, too. On Congress Street, you can stroll through downtown while soaking in the city’s top art galleries.

It’d be a shame not to spend some time on the water in this harbor town, so be sure to book one of the many boat tours that offer a cruise around the bay. Our picks? An Odyssey Whale Watch tour to see marine life like seals and porpoises or the sunset cruise by Casco Bay Lines.

(Main image: AZAdam used under a Creative Commons Attribution-ShareAlike license)

Long weekend in Portland, Maine was last modified: June 26th, 2019 by Marissa Willman
Author: Marissa Willman (786 posts)

Marissa Willman earned a bachelor's degree in journalism before downsizing her life into two suitcases for a teaching gig in South Korea. Seoul was her home base for two years of wanderlusting throughout six countries in Asia. In 2011, Marissa swapped teaching for travel writing and now calls Southern California home.