Our Favorite Ways to Spend the Holiday Season Around Portland, OR

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Portland. This charming Northwestern city punches well above its weight, boasting beautiful and varied scenery, famously independent and unique neighborhoods, and innovation all in a city that’s yet to break 4 million. If you’ve chosen Portland as your holiday season destination, you won’t be disappointed, with so much happening here year-round. Read on for some of our favorite festivals and events here around Rose City.

Pittock Mansion Christmas

Overlooking the Portland region, the Pittock Mansion is as gorgeous as it is enchanting, with its series of holiday season exhibits for all to enjoy. Aside from the breathtaking views, Pittock Mansion also offers a number of hiking and outdoor activities, beautiful flower beds, gardens for photos, and this year, a zany exhibit of lovable critters doing the holiday season their way. This is a great, relaxed, low-stakes activity for groups, families, friends, couples, and solo adventurers alike to enjoy one of the Portland area’s most breathtaking sights during the holiday season.

Holiday Ale Festival

The Portland Holiday Ale Festival is a great outing and way to enjoy some of the Portland area’s best in food and beer, owing to the region’s strong heritage in small businesses, microbrews, and grassroots gastronomic culture. Take the whole party out to Portland’s Holiday Ale Festival and warm up with a selection of over fifty beers and ciders, accompanied with a number of holiday season treats and delicacies all-around a towering Christmas tree. Bring your appetite and your friends to the Holiday Ale Festival while you’re in Portland this holiday season.

Holiday Express

A great option for families and those traveling with younger members in their party, the Holiday Express is a magical journey along the Willamette River and some of the city’s most iconic sights in this holiday-themed event. Visitors will ride in one of Portland’s beloved steam locomotives and enjoy sights, songs, and the smells of the holiday season as Santa, his elves and the party goes on inside the train during the trip! Complete with shows, entertainment, song, dance, and packed with holiday season festivities, the Holiday Express is a memorable option for any family and younger travelers.

Crafty Wonderland

Get your holiday shopping done all in one spot and see some of the best in Portland’s independent art, creativity, and small business. Crafty Wonderland is an event that only happens twice a year, where visitors pack the grounds to score a true one-of-a-kind item, whether clothing, jewelry, artwork and prints, fragrances and soap, DIY kits, books, cards, and of course, food. For all those creative outlets and interests, whether it’s gardening, construction, cooking, fashion, or photography, there’s something for everyone to explore and enjoy at Crafty Wonderland. Catch this massive event and get to meet and shop some of Portland’s finest in the arts all in one spot, Crafty Wonderland!

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