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Portland from the Rooftops

There is a story about the roof of the old Eastland Hotel (now the Westin) in Portland, Maine. The Eastland has a lot of stories connected to it. When it was built in 1927 it was one of the most elegant, and the biggest hotels in New England north of Boston. Charles Lindberg, fresh from his solo flight across the Atlantic, was one of its first guests. Eleanor Roosevelt was once refused a room because of her yappy dogs. The story I’m referring to, however, takes place in 1988 and involves somebody maybe as famous as Lindberg, but arguably less accomplished, Ozzy Osborne.

Oz, it is said, fresh from a concert, a guest of the Eastland, decided to rearrange the pool furniture on the roof by tossing the chairs and lounges to the street some 10 stories below. For his efforts, Oz, the story goes, got a grand police escort to the edge of town and was asked to never return to Portland, Maine again. Is it true? Honestly, I can find a lot about Lindberg out from history books but little about Ozzy Osborne, so we’ll just call it an urban legend.

Regardless of the veracity of that story, however, I can confirm that no pool now sits up top of the Eastland/Westin. Instead, you’ll find Top of the East, one of the oldest, most elegant, and fun places to catch a drink and take in a rooftop vista of Portland, Maine. The 360-degree view, over Portland Harbor, the city, harbor, and Back Cove, is impressive. At night it’s awe inspiring.

a large brick building

If you want to get closer to the water, get some salt air up your nose, the newly built Canopy Hotel on Commercial Street, right next to the docks, also features a rooftop bar, the Luna. You can sip on a Cosmo and watch the ships come in from all the cosmopolitan ports in the world.

a boat sitting on top of a building

Of course, the ultimate rooftop view of Portland is also the oldest rooftop view of Portland, from the top deck of the Portland Observatory.

From there you’re at the highest point of the Portland peninsula. Lemuel Moody builds the 86-foot-high Observatory in 1807 to be a communication station for the port. From high, with a state-of-the-art telescope, Moody can see thirty miles out to sea, and he informs subscribing merchants that their vessels are approaching by hoisting signal flags. A potent symbol of Portland’s maritime history, the Observatory is today the ONLY remaining maritime signal station in all the United States, a magnificent intact survivor from the Golden Age of Sail. If you’re in Portland in the summer don’t miss the amazing museum that the tower is today, and don’t miss the unparalleled view of Portland from its top deck.

a tall building in a city

But maybe you’re just frugal like me (my wife would say cheap), and you want a mellow option where you can just hang out by yourself, taking in the view. Well, how about brown bagging it and going to some of my favorite rooftop establishments, the top of almost any parking garage in downtown Portland. Portland’s peninsula is no more than a mile wide and there are fantastic views from the tops of almost all of our parking garages. Nobody ever thinks about the tops of parking garages. They’re underrated and all you photogs and vista seekers coming to Portland, Maine should take note.

a large city landscape

Want to see the Casco Bay Bridge go up and down? You can’t beat the top of the Holiday Inn’s parking garage on Spring Street. Want to see the harbor tides go in and out? The top floor of the Casco Bay Ferry Lines parking garage on Commercial Street is for you. How about a view up Munjoy Hill to the Observatory and out the harbor to Spring Point Light? Seek out the parking garage by the Hampton Inn on Fore Street. Here’s the view from the Holiday Inn’s garage on a spring day. Count the lighthouses. Count the boats.

And that brown bag? Is it a libation? Just be aware here’s a law against open containers of liquor in public in Portland, Maine. If the cops ask you what’s in the bag, I’ve never heard of you…..or Ozzy Osborne.

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Written by Ross – Portland History Tour Guide

Referred to by his family as a “fuzzy foreigner”, Ross grew up in Nova Scotia, Canada, fell in love with a woman from Boston, and has been in Maine raising his family for over 20 years now. He loves Maine and loves his job as a tour guide, both for the interaction with new people it affords him (don’t be surprised to get as many questions as you ask) and the constant exploration he is always making of the many intricate and fascinating links between his adopted state and his homeland.

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