Portland is an incredible destination for year-round adventures but during the fall and winter months it is a downright magical place to be. Whether you’re itching to discover what makes the city weird or craving a Pacific Northwest holiday, the City of Roses is guaranteed to deliver on a family vacation you’ll never forget. Put in for your days off and get your travel itinerary ready, we’ve put together a guide to three perfect days in Portland, and it includes all of the must-experience major attractions and under-appreciated to-dos the city has to offer. Read on to find out more.

Day 1

photo: iStock

Take a ride on a Portland Street Car. This very Portland-y mode of transportation takes you right through the popular Pearl District where you will find one of the city's most iconic stores: Powell’s City of Books. You can’t leave Portland without perusing the largest new and used bookstore in the world! Powell’s takes up an entire city block, has 9 color-coded rooms with over 3,500 sections and approximately 1 million books. Tie up all of your holiday shopping in this one cool spot!

Celebrate the last of the harvest season, with a trip to Beaverton’s Farmers Market—Oregon’s largest all-agricultural market. You’ll find fresh local produce, artisan food products and some of the best local entertainment. Fuel up with some tasty bites while taking in the home-grown musical flavor! Note: the market is only open through the end of November.

A visit to the Oregon Zoo is a must while you are in town. If your visit takes place late November through December you are in luck. Zoo Lights is one of Portland’s most iconic holiday traditions. The event draws thousands of spectators eager to view the more than 1.5 million lights on display across the property.

Time to check into your hotel! We recommend a Marriott International hotel; they have created a shopping package that takes advantage of Oregon’s tax-free shopping (bonus: free money over the holidays!). Click here to learn more and save this holiday season.

Day 2

photo: chw4r7z via flickr

There’s no better way to start your day than with a coffee from one of Portland’s famous roasters. Grab a cup at the Pearl District's Coava where you can also purchase a bag of beans to take home with you and savor.

If live theater is your thing, indulge in the spirit of the season while taking in a show at the Center Stage at the Armory. This theater is home to the largest theater company in Portland and one of the top 20 regional theaters in the country. You can catch The Second City’s A Christmas Carol: Twist Your Dickens from Nov. 27 through Dec. 23 for a humorous take on the classic tale. Or purchase tickets to A Christmas Paired with Winter Song, a touching holiday story accompanied by the most beloved tunes.

For a taste of Portland’s superior ethnic dining experience, head to Nak Won in Beaverton for scrumptious Korean cuisine with the reputation for being some of the best food in Portland. This area is also home to the renowned Vida Veggie, which serves incredible organic Latin-inspired vegetarian and vegan food that even meat-eaters will appreciate.

After you’ve fueled up for the afternoon, embark on the Beaverton wine trail. This adventure will take out to Cooper Mountain Vineyards at the top of Cooper Mountain in southwest Beaverton. From there you move on to Hamacher Wines at Ponzi Historic Estate where you can sip on wines from both Hamacher and Ponzi.

Day 3

photo: The Oregon Garden

A visit to Portland isn’t complete without a visit to Pioneer Square. Grab a cup of coffee and enjoy the festive atmosphere. The Square’s tree lighting takes place on Nov. 23 and Santa is sure to make an appearance. Take advantage and get your family pics with the jolly old saint.

Take a stroll in one or two of the scenic parks that call the Pearl District home. Jamison Square is one of the area’s most iconic parks. During the hot summer months, families flock to it to let their kids cool off in its interactive fountains that are designed to function like tidal pools. While the water doesn’t run throughout the colder months, it maintains its appeal with plenty of stone benches to sit and relax on while enjoying the festive tree and decorative lighting.

For an expansive park with a play area try North Park Blocks. Or, wind your way along paths through Tanner Springs Park where you can experience a preserved wetland with a spring-fed pond located right in the heart of the Pearl! When you’ve worked up an appetite, there is an array of family-friendly eateries in the area. Grab a slice of pie at Hot Lips Pizza or dine in style at the ever-popular Andina.

If holiday photos and shopping are on your list of to-dos, head to the Beaverton area's Washington Square Mall where you can visit Santa’s Headquarters and grab a quick shot with the magical man himself and pick up some gifts for your loved ones. If you get done fast, there are coffee shops, parks and the Tualatin Nature Park nearby for some extra fun.

End your stay with a visit to Portland’s Japanese Garden where you can immerse yourself in the Japanese culture while checking out exhibits, wandering through the gardens and a bite and sip in Unami Café before heading back to check out of your Marriott hotel.

—Annette Benedetti


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3 Perfect Days in San Francisco 

3 Perfect Days in Seattle 


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