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11 Christmassy Things to Do in Portland, Maine
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11 Christmassy Things to Do in Portland, Maine

Picture of Christopher Crosby
Updated: 14 November 2017
Throw a blanket of powder down, and Portland, all brick and cobblestone, comes into its own charm. From classic ballet and ice sports to time travelling and boozy twists, find out the best Christmastime things things to do in Portland.

Sing along with the Portland Symphony Orchestra

Most cities feature a Christmas music extravaganza—what sets Portland’s Magic of Christmas apart is the interchange between orchestra and audience: singalongs, children plucked from the crowd to conduct, and a willingness to experiment with visual performers. Hearing favorite carols will put you in the perfect mood to pool outside into the wintry night air to keep the holiday magic going.

Merrill Auditorium, 20 Myrtle St, Portland, ME, USA, +1 207 842 0800

Sled the Eastern Promenade

When skies gray in winter, locals break out sleds and zoom through fluffy powder down the Eastern Prom‘s steep slope. Casco Bill, a beautiful hill with views over the blue Atlantic, is usually uncrowded in winter and offers boundless sledding possibilities.

Enjoy egg nog overlooking the Old Port

Portland has no shortage of great cocktail bars, and sipping egg nog while overlooking the cobblestone streets is a great way to warm up to Christmas. Few places do cocktails as well as Hunt + Alpine, where Nordic themes meld naturally with the wintry season come Christmas. Woodford Food & Beverage pours a good egg nog, and North Point offers a cozy location to stow away for hours.

Holiday trees in Portland, Maine
Holiday trees in Portland, Maine | © Paul VanDerWerf / Flickr

Shop Merry Madness

Old Port has no shortage of places to shop and, on December 7, no shortage of time either. Merry Madness Shopping, Portland’s annual shopping bonanza, sees boutiques and craft stores leave their doors open to 10p.m. or later, perfect for last-minute shoppers. Plus, between 4–6p.m., shoppers can receive a goody bag of snacks and a wine glass, good for a complimentary pour to stay fortified through the long night ahead.

Watch the Portland Christmas Tree Lighting

Maine doesn’t lack for pine trees (hello, Pine Tree State) but the massive, shapely pines taken from the wilderness look especially impressive decorated with lights. Portland’s official lighting ceremony is a Maine tradition and draws a festive crowd to Monument Square with singers and, of course, Santa. There’s egg nog, an orchestra-led singalong, a live band, and free horse and wagon rides.

Monument Square, 456 Congress St, Portland, ME, USA