When I first lived in Portland, any time without a working car (times that are frequent when you’re young and broke) felt like a death sentence for ski season. With Maine and New Hampshire’s biggest resorts hours away, and even the closest community hills a good distance down Routes 26 or 302, skiing was off the menu far too often during those years. Without a network of long-distance resort shuttles like in the Rockies and out west, a vehicle is a necessity.

Since then, however, I’ve discovered the opportunities for skiing in Portland … and the great history of skiing across multiple disciplines in the Forest City.

Portland’s ski history stretches back nearly a century, to a heyday of Portland-based skiing in the 1920s. Winter carnivals were a big deal in the city back in the ’20s, and thousands came to watch (and participate in) winter events, including skiing. The biggest ski feature at the time was a ski jump, which launched skiers off the West End and toward St. John Street.

Skiers of the era also made use of Portland’s location as a railroad nexus, taking trains to go skiing throughout Maine and New England. Trains shuttled riders from two terminals to Bridgton, Rangeley, Farmington, and even Conway, New Hampshire; St. Johnsbury, Vermont; and Quebec.

Both jumping and ski trains saw their decline and eventual extinction in Portland, though both had small resurgences in the last few decades. During a few recent winters, Sunday River, Sugarloaf and Loon hosted the Downtown Showdown in Monument Square. The event, which featured skiers and snowboarders on a man-made slope with jumps and rails, hasn’t been held since 2011.

The most recent attempt at a Maine ski train came from Sunday River in the early 1990s. From 1993 to 1996, the Silver Bullet Express carried skiers to the Newry resort. It was an attempt by then-owner Les Otten to connect the resort to Maine cities (and Boston beyond), but it’s existence predated the Amtrak Downeaster and floundered before that regular service came to Maine in 2001.

In terms of honest-to-goodness downhill skiing in Portland, the best luck I’ve had is on the Eastern Promenade. The wide-open hill that drops from the Eastern Promenade road to Cutter Street and the Atlantic beyond is a popular sledding hill, but it’s workable for skiers and snowboarders as well. My favorite descent, short but steep, is from the Eastern Promenade playground down to the upper East End Beach parking lot and Midslope Trail. The route is unnamed (as far as I know) but flows through a small stand of trees and offers a half-dozen solid turns.

For those that prefer the urban appeal of rails and other man-made jibs, Portland is full of architectural wonders – the same ones frequented by skateboarders. However, save a few in Payson Park and Deering Oaks, property owners and Portland police tend to frown on skiers hitting these features.

While the world of ski jumps is no longer in Portland, and there’s precious little downhill skiing to be had, the city shines as a playground for Nordic skiers. Just last week, USA Today named Portland as one of the nation’s 10 best places for urban cross-country skiing.

It’s an honor that shouldn’t surprise any locals who can see folks tooling around the roads and sidewalks of the Old Port on Nordic skis whenever there’s substantial snowfall. Considering how the neighborhood seems to shut down after anything more than a few inches, you can’t blame locals for breaking out the skis and exploring.

Beyond the snowy roads, the Portland Trails network offers loads of options for Nordic skiers. The marquee option is definitely the Back Cove Trail, a flat look stretching over three miles with a choice view of the city skyline. There’s also the aforementioned Deering Oaks and Payson Park, and for the more adventurous, a ferry trip opens up the Peaks Island trails to very dedicated skiers.

So, if you find yourself stuck in Portland this winter, don’t lament the fact that you can’t make it to the mountains. Instead, revel in Portland’s history as a home for skiers and get out to explore her trails yourself.

Josh Christie is a freelance writer and lifetime outdoors enthusiast. He shares column space in Outdoors with his father, John. Josh can be contacted at:

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