October 2018 | view this story as a .pdf

Night owls soar to these magnetic spots for drinks, bites, and especially the stellar views.

By Olivia Gunn Kotsishevskaya

On a crisp fall night, metro-Portland restaurants and bars set up the perfect visual vignettes.

Reflections

Windows stretched to the ceiling showcase the sparkle of Maine Wharf, on Portland’s busy waterfront, catering to the inviting warmth of Scale’s interior.

Sure, you can delight in endless oysters and Manhattans at the fresh bar until closing time, but if you’re looking to feast your eyes, tables 1-12 are positioned right off the water along Scales’s tall, paned windows. Reserved for groups of three to four, these tables make for the perfect excuse to invite your favorite couple out for a night on the town.

Neverland

You’ll feel like one of J.M. Barrie’s ‘lost boys’ climbing the stairs of the whimsical Treehouse Cafe. It’s not the harbor view that comes to mind when one thinks “Maine scene,” but it’s an interior whirl for the imagination.

Up a short flight of steps, you’ll enter what seems like room after room of welcoming, glowing tables and nooks draped with vines and twinkling lights. Each spot makes for a perfect nest for you and yours to enjoy a spicy glass of red and a bowl of saucy mussels on a fall evening.

The ambiance of this cafe tucked above Stevens Avenue is enough to feed the senses, but a visit to the leaf-canopied deck proves we’re more than a city of boats and piers. Sometimes the best view is right in front of you.

On the Tide

If you want Casco Bay sunsets and sails, you want to be at Dockside Grill. Just a short drive out of Portland, this Falmouth restaurant is a jewel on the coastline.

With plenty of seating for a family meal and a never-ending wraparound bar, the Dockside fits any evening plan. Sip an autumnal cocktail like the Cider Mule ($10) while cozied up by the fire, or take a table for two by oceanfront windows and enjoy a fresh Maine meal with a local brew.

The Highlight

There’s no other spot like it in Portland. It towers over Congress Street as though it were built for the great Gatsby himself. But the Westin Hotel’s bar and lounge, Top of the East, is just for Portland. It dates to 1927. It’s so high off the ground that Lindbergh christened it during his famous visit to our city.

Offering a shimmering vantage above Portland Museum of Art, Congress Square Park, and the harbor, Top of the East is the breathtaking moment you hold for treasured nights. You’ll find night owls here at a high-top table enjoying a Ye Olde Fashioned ($14) after a romp in the Old Port. It’s a last stop on your way to the moon.