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About the Author

Kay Kingsman

Kay Kingsman is a travel blogger based in Portland and the voice behind The Awkward Traveller blog. When she’s not recounting her hilariously embarrassing adventures abroad, Kingsman uses her platform to provide tips and information to make travel more accessible and attainable. She’s featured in Forbes, Buzzfeed and Dame Traveler.

6 Must-Visit Black-History Spots in Oregon

November 22, 2022
When I thought about the rich, complex and deep-rooted history of Black people in America, Oregon didn’t come to mind. Stunning natural beauty around every corner? Definitely. Delicious and innovative restaurants popping up every month? Oh, for sure. But … Black history? That was one aspect of Oregon that was harder to grasp. More
found in
Culture & History ,

Find Art, Culture and Sensational Shopping in Milwaukie

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August 1, 2022
Milwaukie was originally named after Milwaukee, Wisconsin, but this city just south of Portland has its own, entirely Oregon history. Fusing a small-town vibe with big-city culture, it’s also a great place to visit. Easily accessible by car, light rail, foot or bicycle, Milwaukie brims with public art, a bustling farmers market with over 70 vendors, and independent businesses creating everything from custom tea blends to quirky paint-by-numbers kits. More
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Portland Region , Milwaukie , Favorite Trips , Cities , Trip Ideas ,

How to Eat Well on an I-5 Road Trip in Oregon

February 22, 2022
My first Oregon experience was heading up Interstate 5 (or I-5) to Corvallis from California nearly 10 years ago for university, watching the scenery rapidly change from the desert mountains of Southern California to the lush Oregon terrain. Safe to say I was hooked. More
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Willamette Valley , Favorite Trips , Trip Ideas ,

Oregon-Made Film Wins Spot at Sundance

January 13, 2022
Bringing the snowcapped mountains of Southern Oregon all the way to the largest independent film festival in the United States, the short film “You Go Girl!” will premiere on January 20 at the 2022 Sundance Film Festival. More
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Southern Oregon , Ashland , Filmed in Oregon , Culture & History ,

Oregon Tribal Spotlight: Klamath Tribes

October 8, 2021
You may be familiar with Southern Oregon’s Klamath Basin, a mix of swaying grasslands, serene lakes and dense forests. You may not have known the rich history and culture of the Klamath Tribes embedded in the snowcapped mountains. One of nine federally recognized Indigenous Nations in Oregon, the Klamath Tribes consist of three groups who have inhabited the area since time immemorial: the Klamath, Yahooskin and Modoc. More
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Southern Oregon , Klamath Falls , Native American Culture , Culture & History ,

Road Tripper’s Guide to the Portland Region

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August 12, 2021
In Portland the vacation vibes can switch between climbing mountains and window shopping in the city at the snap of a finger — or a turn of your car’s ignition. You can be exploring waterfalls and dog-friendly trails in the morning and tasting wine, kiteboarding or spotting gray whales in the afternoon. More
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Portland Region , Portland , Favorite Trips , Trip Ideas ,

How to Celebrate Juneteenth in Oregon

June 15, 2021
Oregon, mark your calendars for June 19, 2022, for Juneteenth celebrations featuring live music and performances, food and goods from local businesses, and the honoring of Black history in the state and across the nation.  If you’re unfamiliar with the holiday, Juneteenth is the acknowledgement of the collective end of slavery in the United States and is a long-standing African American holiday that honors the resistance and resilience of Black people in America. More
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Culture & Heritage Events , Events ,

Tips for Your First Oregon Campervan Experience

May 13, 2021
Unpredictable is the name of the game in the campervan world — apparently, it means getting used to having no cell service. I mean, I’m a Millennial — I don’t do anything without my phone. But digitally disconnecting is half the excitement — it’s ultimately what kept me coming back over the years, after I took my first campervan trip, admittedly a bit ill-timed, during Portland’s 2016 “snowpocalypse.” What was supposed to be an easy weekend getaway to the Coast in my friend’s old minivan... More

Road Tripping While Black in Oregon

October 9, 2020
When you prepare for a grand road trip, a few questions might run through your head: Is the driving playlist up to date? When was the car’s last oil change? Are there enough snacks? But for BIPOC travelers (Black, Indigenous, people of color), there are other questions that might arise. More
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Favorite Trips , Trip Ideas ,

Support Oregon’s Black-Owned Businesses

July 29, 2020
Throughout Oregon, you can find an array of cuisine, from African and Caribbean to Southern and Pacific Northwestern, put forth by Black business owners. You can find friendly shop owners welcoming to all. They deserve your support.  More
found in
Trip Ideas ,
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