Doing Portland, Maine, by day and by night

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Portland offers a study in New England architecture with its 19th century brick buildings.
Portland offers a study in New England architecture with its 19th century brick buildings. Photo Credit: Danny King
Upon researching the influx of new hotels in Portland, Maine, one hotelier joked that there should be a subway line connecting Maine's largest city to Brooklyn because of the hipster migration


Which made it all the more enlightening to discover how family friendly the town and its environs can be.

A family could take a day-night approach to exploring the area: take the kids to visit the surrounding beaches, lighthouses, parks and islands by day, then hit up Portland's restaurants by night.

This approach works especially well when the weather cooperates. One obvious destination is due south to the Portland Head Lighthouse and the adjoining Fort Williams Park, home to Maine's oldest lighthouse, inspiration for an iconic Edward Hopper painting and a view postcards don't do justice.

Nearby, a meandering drive is just as rewarding and provides easy access to Cape Elizabeth, Two Lights State Park and Higgins Beach, all brimming with New England coastal serenity. Top it off, literally and figuratively, with some soft serve at Red's Dairy Freeze, South Portland's barn-shaped institution, and everyone's in a good mood (if not sugar-hyped).

Meanwhile, a 45-minute drive northwest of Portland takes you Bridgton, Naples and a host of other hamlets dotting the area's dozens of lakes, with Sebago Lake being the largest. Notably, Naples Lobster Pound (closed each October to April) offers nothing in the way of formality and everything in the way of authenticity, not to mention the sweetest lobster imaginable.

Those looking to explore offshore can hop the ferry to make a daytrip out of exploring the Casco Bay Islands, including Peaks Island, Great Diamond Island and Cliff Island, for biking, hiking, kayaking and other activities.

No car is no problem in Portland, even with the family. A veritable diorama of late-19th century brick-and-stone architecture (much of the city was destroyed in an 1866 fire), Portland is extremely compact and walkable, and its locals embody a combination of artsy funkiness and down-to-earth ruggedness (the city's motto is Resurgam, which means "I will rise again" in Latin).

Old Port is the most obvious destination, with its shops and restaurants as well as museums, such as the Portland Science Center. Farther east, though, is Munjoy Hill, which includes the Portland Observatory as well as the shopping and restaurant districts of Congress Street and Washington Avenue.

Proudly boasting the most restaurants per capita in the country, Portland offers a selection of eateries sophisticated enough for hipster foodies while lacking the pretention that would keep families away. Top of our list was Union, which is part of the Press Hotel but would stand on its own in any New York borough (the chicken pozole appetizer and salmon with red curry and squash were standouts). Munjoy Hill's Terlingua's combination of Mexican, Caribbean, Southern and barbecue cuisines would shine anywhere. Ramen hounds (count me as one) will appreciate Pai Men Miyake's combination of noodle soups, drink selection, modern-Asian design and youthful vibe.

The Westin Portland Harborview, which opened as the Eastland in 1927, reopened after an extensive renovation in 2013.
The Westin Portland Harborview, which opened as the Eastland in 1927, reopened after an extensive renovation in 2013.

Hip and historical hotels

Portland-area hotels have made the type of improvements that allow guests plenty of comfort and creative design should the weather fail to cooperate. Our partially hosted stay was at the Westin Portland Harborview, which opened as the Eastland in 1927 and reopened in 2013 after a two-year full remodel.

The one-bedroom suites are huge and tasteful, the lobby bops with big-band jazz and the 15th-floor Top of the East offers small bites with stunning views of Casco Bay and New England.

Those looking to stay closer to Old Port can choose from the Portland Harbor Hotel or Hyatt Place Old Port, which are across the street from each other.

The Portland Harbor Hotel, its 101 rooms renovated this year, boasts an urban-nautical design with navy blues, grays, lots of mahogany and custom-made furnishings from Maine-based Thos Moser. Formerly known simply as the Harbor Hotel, it also boasts the outdoor Eve's at the Garden during the summer.

Opened in 2015, the Hyatt Place Old Port has a modern, artsy street presence unlike any other within that chain and takes that vibe inside with touches such as an orange-hued, translucent light-fixture sculpture called Kelp. The hotel's Glass serves craft cocktails and small plates, while the hotel takes on an eco vibe by getting a quarter of its power from the state's largest solar array.

The Press Hotel opened as part of Marriott International's Autograph Collection in the city's old Press Herald building in 2015, and its sophisticated vibe extends to its Inkwell lobby bar and a two-story art piece constructed of old typewriters called Swarm.

South of town, the 23-room Higgins Beach Inn (open from May to October only) reopened this year with updated facilities and a new, 80-seat restaurant called Shade Eatery.

The Inn by the Sea in Cape Elizabeth has larger beach suites for multigenerational family travel.
The Inn by the Sea in Cape Elizabeth has larger beach suites for multigenerational family travel.

Finally, the posh Inn by the Sea in Cape Elizabeth, which added its 1,350-square-foot Beach Suites a few years ago for multigenerational travelers, also received renovations this year. The five-acre resort includes the full-service restaurant Sea Glass and gives guests beach access via a wood-plank walkway through an animal preserve, which offers safety to local species such as the New England cottontail. And, yes, they refer to the preserve as "the Rabbitat."

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