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2018 Holiday Events in Portland Maine

Holiday DecorationsIt’s wonderful to celebrate the holiday season with family and friends. You may want to get everyone together and explore some of these holiday happenings in Portland. There are plenty of festive events for everyone to enjoy.

2nd Annual Ugly Sweater Crawl
Saturday, December 8th

Break out your tackiest holiday sweater, shirt, pants, or other accessories and join the fun in downtown Portland.

East End Holiday Stroll
Saturday, December 8th

Explore the East End shops, boutiques, restaurants, and cafes while doing your holiday gift shopping.

Portland’s Holiday Express
Saturday, December 9th & 15th & Sunday, December 9th & 16th

Enjoy a ride on vintage rail cars with Santa and his elves through the heart of the city.

Old Port Winter Holiday Historic Walking Tour
Every Saturday in December

Bring the family on this historical adventure and learn about Old Port’s rich history and places of interest. 90 minute walking tour.

Horse & Wagon Rides
Fridays, Saturdays & Sundays through December 16th

Enjoy a free 30 minute horse & wagon ride through the beautifully decorated historic downtown Portland. Pick up and drop off in Monument Square.

Winter Lights
All Season

Come and see the fantastic colors and shapes of these beautiful winter lights that bring radiance and warmth to downtown Portland throughout the holiday season.

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