Portland, Past Peak

If you Google “when to go to Portland,” you’ll find that most tourists head to this little city in southern Maine in the summer. Winter, too, has a certain allure for those in search of picture-book New England landscapes, when Portland can be a cozy stop on the way to skiing and other snowy outdoor activities. But I especially love old seaport cities in the fall, as the bleakness of winter is just beginning to creep in. That’s why I suggest a trip to Portland after the leaves have fallen and before the snow, when it’s cold enough that you need a moment to mentally prepare yourself before stepping out into the wind, but not so cold that you can’t quickly warm yourself in a coffee shop, bookstore, or small independent shop on a cobblestone street.  

Portland is close enough to go for the day or weekend, only a three hour drive from New London or Hartford and even less of a trek from northeastern Connecticut. (You can also get there by Amtrak.) Despite the fact that it’s a popular destination and apt to be crowded in any weather, taking a November trip to Portland can still make you feel like you ventured ever so slightly off the beaten path.

What to See & Do

-Walk around the Old Port. This is the part of the city that anyone intrigued by the past will instinctively be drawn to. It’s where you’ll find touristy shops and restaurants occupying renovated warehouses, but also charmingly uneven streets, eclectic historic architecture, and one of New England’s last remaining working waterfronts. Portland is Maine’s largest city, with a year-round population of 66,000. But the intimate grid of the Old Port makes it feel much smaller – and paradoxically much greater, too, as if the city extends far beyond its borders due to its ties to the sea.

-Seek out street art. From Wyland’s “Whales Off the Coast of Maine” near the Maine State Pier, to detailed depictions of historic Portland scenes adorning Old Port walls, to a growing number of more colorful and abstract designs, the streets of Portland are brightened by murals. As you walk, keep an eye out for local creativity displayed on the walls.

-Stroll the Eastern Promenade. Not far from the Old Port, where Portland’s coastline rises above Casco Bay, the Eastern Promenade is a combination park, multi-use trail, and expansive scenic overlook. In the summer, people come to swim at the public East End Beach or view Fourth of July fireworks; in the fall, it becomes a quiet spot perfect for appreciating the beauty of nature.

-Look out for lighthouses. Maine’s rugged coast is a paradise for lighthouse fans, and there are several within minutes of downtown Portland. Though some are better seen by boat, others can be reached by car and on foot. Portland Head Light, in Fort Williams Park in Cape Elizabeth, looks like a romantic painting of a classic lighthouse on a rocky coast. Spring Point Ledge Light, at Fort Preble on the campus of Southern Maine Community College in South Portland, is a black-and-white beacon at the end of a granite breakwater. Also in South Portland is the Bug Light Park Lighthouse, aka Portland Breakwater Light, a comparatively pocket-sized lighthouse beside a paved walking path with views of Portland Harbor.

-Warm up with hot coffee. (Or tea, or cocoa.) It’s not hard to find a cozy coffee shop in Portland; spend a few minutes in any neighborhood and you’ll probably stumble on a hip little storefront where they take their coffee very seriously. In the Old Port area, Bard Coffee is a lively gathering place, and Higher Grounds feels like a little hideaway. (Of course, there are even more restaurants to choose from in this acclaimed foodie city. To grab some lunch while bypassing the scene, stop at Portland Public Market House; there’s plenty of no-frills seating in this building on the site of Portland’s original market square, and a variety of vendors and cuisines means there’s something for everyone.)

-Go shopping. Portland is packed full of unique stores that tempt you to duck inside and check out what’s in stock. Among the many bookstores, Longfellow Books and Sherman’s Books & Stationery will make you want to browse for hours. For cheesy souvenirs, there’s local standby Cool as a Moose, and for classier mementos of your trip, try Maxwell’s Pottery for delightful housewares or Sea Bags for recycled nautical totes.


-For the most part, exploring Portland is much more fun on foot than in a car. There’s metered street parking downtown (free on Sundays) and many parking lots and garages to choose from.

-If you’re coming from Connecticut, it’s tempting to combine Portland with other destinations that have off-season appeal. Consider a brief stop in Old Orchard Beach, where the famous pier takes on a whole new beauty in cold weather, or an extra afternoon in Freeport, where the popular outlet stores will be less crowded at this time of year. Or take a few days to explore both Portland and Portsmouth, New Hampshire, another historic New England seaport city that’s captivating in the fall.

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