Weirdest Things To Do in Portland, Oregon

56 Weird & Wonderful Things to do in Portland, Oregon

Portland is really… REALLY weird. We might have stolen the “keep Portland weird” catchphrase from Austin, Texas but I’d argue that if our Unipiper was leading us into a battle over weirdness, we would undoubtedly win.

As someone who was born and raised in Portland, I’d like to think I know a few things about this quirky little city. If you’re headed to Portland and want to get a little weird, here are 56 ways to do it… Enjoy!

Portland, Oregon: Weird & Unusual Things To Do - Lost Hen

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56 Fun, Unique, Weird, and Unusual Things to do in Portland

1. Test Your Limits at Creepy’s

Portland has its fair share of “weird” bars, but Creepy’s might just take the cake. If the idea of dolls and toys coming to life freaks you out, this might not be the place for you. 

If you don’t mind drinking while the taxidermied animal heads and portraits of Victorian children with moving eyeballs stare back at you, this may be your idea of a good time! Oh, and don’t be surprised if the vintage toys and creepy clowns suddenly start moving on their own.


2. Visit the Clown Room at Funhouse Lounge

Portland, Oregon: Weird & Unusual Things To Do - Clown Room, Funhouse Lounge

The Funhouse Lounge serves up unique nightly shows like Dominatrix Improv or Burlesque Stand-up Comedy that alone would make this a worthy stop on our list of weird things to do in Portland. But the icing on the cake is their clown room where you can sip a cocktail while surrounded by hundreds of creepy clown pictures. Guaranteed to induce nightmares for any coulrophobiacs out there.


3. Visit the World’s Smallest Park

Weird Things to do in Portland, Oregon: Mill Ends Park - The Smallest Park in the World

At just 452 square inches, Mill Ends Park is the smallest park in the world according to the Guinness Book of World Records. You can find it at the corner of SW Front Avenue and Taylor Street. Be sure to stop by this weird little park for a photo while wandering around downtown Portland!


4. Explore the Shanghai Tunnels

Have you ever heard of “shanghaiing”? It’s the illegal capturing and selling of able-bodied men to sea captains and it used to be an underground operation in Portland, Oregon. Literally underground. The Shanghai Tunnels run underneath the city connecting the downtown area to the Willamette River. According to legend, men were drugged (or simply overly intoxicated), kidnapped, dragged into the tunnels, and then held captive until they could be sold.

You can take a tour of the underground tunnels and learn more about Portland’s sordid past.

Book a Portland Ghost Tour


5. Buy a Joint (Don’t Worry, it’s legal!)

Portland, Oregon: Weird & Unique Things To Do - Recreational Marijuana

If you are over the age of 21, the use of recreational marijuana in a private residence is legal in Oregon. And you’ll find plenty of dispensaries all over Portland where you can walk in, talk to an expert about strains, and then walk out with a joint. Just don’t tell mom. Oh, and don’t try to smoke in public or take it across the border with you.


6. Zoom Around Town on an Electric Scooter

The electric scooter craze has arrived in Portland and they are now super easy for busy commuters and carefree tourists to rent. Just sign up for the mobile app by one of the three companies piloting the technology – Bird, Lime, or Spin – then locate an available scooter and use your app to start your scooter rental. Off you go on a weird adventure around town!


7. Visit the First-Ever Voodoo Doughnut

Weird Things to do in Portland, Oregon: Voodoo Doughnut

A lot has changed since Voodoo Doughnut opened its first location in Old Town Portland. For starters, the famous Voodoo Doughnut Eating Challenge, in which contestants would smash a .5-pound donut, is a thing of the past. And gone are the days when happy couples could get married at Voodoo Doughnut!

With 19 locations in the US, and many more openings on the horizon, Voodoo Doughnut has changed a lot. But if you’re Portland-bound, you can still visit the humble original location at 22 Southwest 3rd Avenue in Old Town.  

Work blue with the chocolate-covered Cock N’ Balls with Bavarian cream filling, add a little spice to your life with the cayenne pepper-infused Ring of Fire, or simply order up the classic Bacon Maple Bar to get a taste of how it all began.


8. Better Yet, Take a Donut Tour

Of course, there are lots of other amazing donut shops in Portland – Blue Star DonutsPip’s Original Doughnuts & ChaiNOLA Doughnuts, and Doe Donuts, just to name a few. 

If you want to try them all, then how about a donut tour?


9. Snap a Photo of your Feet on the PDX Carpet

Weird Things to do in Portland, Oregon: PDX Airport Carpet

The PDX carpet gained notoriety due to its unique design and the fact that people loved to take pictures of their stocking feet on it. It was the weird but classic social media sign that you were coming or going. The famous carpet has been replaced throughout most of the Portland airport with an updated design, but you can still find a small section of the old iconic carpet in Terminal A.

Plus, PDX carpet enthusiasts will be pleased to learn that the iconic carpet is set to feature in PDX’s new terminal, which is set to open soon! And if you really want your iconic Portland airport carpet picture to be amazing, buy a pair of PDX carpet-patterned socks to wear for your photo shoot!

Weird Things to do in Portland, Oregon: PDX Carpet Socks

10. Play Old School Video Games at Ground Kontrol

With over 60 classic video games and 27 pinball machines, Ground Kontrol is a Portland gamer’s paradise. Kids have to leave in the evening when the bar opens so that the adults can really let loose!


11. Eat “Pear and Blue Cheese” Ice Cream at Salt & Straw

You’ll find countless ice cream shops around Portland boasting unique flavor combinations that mix sweet with salty. But the first one to really step outside of the box was Salt & Straw. And to this day they remain the most popular. If you go on a hot day, you’ll undoubtedly have to stand in a line that trails out the door and down the block but trust us, the wait is worth it.

Plus, they’ll let you sample as many flavors as you’d like before settling on your favorite! Do what I do and sample all of the flavors that interest you and then just buy a pint for later.


12. Go Antiquing at Hippo Hardware

When you see the toga-clad hippos painted on the columns in front, you’ll know you’re at the right place. Hippo Hardware is theoretically a salvage and hardware store. But this behemoth 3-story, 30,000 square-foot Portland business also offers “assorted collectibles, trinkets, whatnots, and whoziwhatsits depending on what we get in.”

Not only are you free to rummage through the various assortment of strange knickknacks they have acquired over the years, but it’s strongly encouraged. According to their website, “The spirit of Hippo Hardware is to rejoice in the individual, the unique, and the original.” How Portland weird is that?


13. Sleep in a Haunted Hotel

The Heathman Hotel has been called one of the most haunted hotels in America. Guests report items mysteriously moving around the room, the sensation of someone crawling into bed with them, cold spots, strange noises, and hazy faces staring out of the shadows. Rooms 703, 803, and 1003 are particularly active with paranormal activity.

Stay there during your trip to Portland… if you dare…


14. Pay Tribute to Portland’s Beloved Late Drag Queen, Darcelle

Weird Things to do in Portland, Oregon: Darcelle's Drag Queen Burlesque Show

Walter Cole was born in 1930 and passed in 2023. He had a wife and two children and lived a “conventional” life in Portland before developing his “alter ego” –Darcelle XV. He first wore a woman’s dress at age 37 and until his recent passing he held the title of the oldest female impersonator on the West Coast. You can pay tribute to him and see beautiful ladies performing drag burlesque at his popular Portland venue, Darcelle XV.


15. Sing a “Stripperoke” Karaoke Tune at Devil’s Point Strip Club

Portland has the most strip clubs per capita of any city in the US – one for every  ~11,200 residents. But most of the strip clubs in Portland aren’t exactly “run of the mill”. You’ll find tattooed women with mohawks cutting the heads off of sex dolls with a chainsaw and all types of other bizarre burlesque behavior. Don’t mess with them, they can definitely kick your ass.

Every Sunday night Devil’s Point hosts “Stripperoke”. It’s like karaoke, but with strippers dancing around you while you sing. It’s great fun for the whole family! Just kidding, adults only.


16. Sing Karaoke with a Live Band at “Karaoke from Hell”

Get the chance to feel like a real rock star by singing karaoke with a live band! Every Monday night Dante’s hosts “Karaoke from Hell” where you can pick from the hundreds of song options, stand on stage in front of a crowd of cheering fans, and jam out with a live band.


17. Ride naked at the World Naked Bike Ride

Once a year, hundreds of Portlanders strip off their clothes, jump on their cruisers, and join the World Naked Bike Ride and subsequent awkward naked after-party. It’s great fun, just make sure you add extra cushion to your seat so those bare buns don’t chafe.


18. Try a Boozy S’more at the “Cabin in the City”

As the name implies, step inside the 1927 S’mores Company and you really will feel like you’ve been transported to a cabin in the woods. This rustic shop is all about the camping vibes, which is why this place specializes in all things s’mores. 

But this is Portland, after all, so don’t expect your run-of-the-mill marshmallows and chocolate sandwiched between graham crackers. Try The Original 1927 with a gourmet vanilla marshmallow and bittersweet chocolate ganache. Better yet, go boozy with the Whiskey Salted Caramel or the Bourbon Peach Cobbler. 

They also do a variety of seasonal s’mores that are always creative and delicious!


19. Attend the Portland Oddities and Curiosities Expo

Held in October, the Portland Oddities and Curiosities Expo is “for lovers of the strange, unusual, and bizarre.” If you’ve been looking to pick up some taxidermy, a creepy new outfit, or just an ultra-dark piece of art, attending this expo is definitely one of the weirdest things to do in Portland. 


20. Eat Vegan at the Casa Diablo Strip Club

Does it even get more “weird Portland” than a vegan strip club? No, no it doesn’t.


21. Visit the Freakybuttrue Peculiarium

Portland, Oregon: Weird & Unique Things To Do - Freakybuttrue Peculiarium

The Freakybuttrue Peculiarium is both a museum and a store and is filled with strange oddities that you never knew existed. You must see them to believe it.


22. Get Weird at Wyrd Leatherworks and Meadery

The medieval fantasy-themed Wyrd Leatherworks and Meadery is all about celebrating the cosplay crew. So, if you want to don your fantastical or historical best while sipping homemade mead by the fire, this intimate tasting hall is the spot for you!


23. Snap a Selfie with the Paul Bunyan Statue

Taking a picture with the 31-foot-tall statue of the iconic lumberjack Paul Bunyan is easily one of the most unique things to do in Portland. You’ll find Paul, as he’s known to locals, standing tall in Portland’s Kenton District.

Wondering what he’s doing there? Paul was built in 1959 to celebrate Oregon’s 100th birthday and has now been listed on the National Register of Historical Places!


24. Tie a Plastic Horse to the Curb

As you stroll through the neighborhoods of Portland, you’ll start to notice the metal rings embedded in the sidewalks. These rings date back to the 1800s when they were used to tie up horse carts. The Portland Horse Project began in 2005 when artist Scott Wayne Indiana began tying tiny horses to the unused rings. The movement took on a life of its own and soon people all over the city were tying tiny horses to the rings in their neighborhoods.

If you do add your own tiny plastic horse to Portland’s urban landscape, make sure you snap a photo and tell the community about it on their Facebook page.


25. Watch the Roller Derby Girls get Aggressive

Watch the “Break Neck Betties” take on the “Wheels of Justice” or the “Guns N Rollers” clash against “8 Wheel Assassins”.  We’re talking about full-body contact roller skating. We have been to several Rose City Roller Derby bouts and we still have no idea how this sport works, but they sell beer at the venue so who cares?


26. Hike to the Witches’ Castle

Portland, Oregon: Weird & Unique Things To Do - Witches Castle

The “Witches Castle” is a stone structure that was built in the 1930s as a park ranger station and a restroom for hikers. It was heavily damaged and is now covered in moss and graffiti and is a popular spot for teens to have parties on the weekends. There’s no connection to actual witches, it’s just a creepy old structure along a really beautiful hike in Portland’s Forest Park.

From the Upper Macleay parking lot, it’s about a half-mile hike to the Witches Castle or you can park at the Lower Macleay lot for a bit of a longer walk.


27. See the Swifts Roost at Chapman School

Every year in late August, thousands of Vaux’s Swifts gather in preparation to migrate to Central America and Venezuela. And one place in particular that one swift population has been choosing since the 1980s is a chimney at Chapman School in Portland. Hundreds of people gather on the lawn at the school one hour before sunset to watch the swifts swooping through the air in unison.


28. Make a Wish at the Wishing Tree

Portland, Oregon: Weird & Unique Things To Do - Wishing Tree

This tree on Northeast Seventh Avenue in Portland has been a favorite for those looking to read the wishes of others or make their own wish for years. Jot yours down on a manila tag and tie it to the trunk. It’s sure to come true…


29. Lounge Naked at Collins Beach

Collins Beach is a clothing-optional sandy beach located on the Columbia River on Sauvie Island. If you aren’t a fan of tan lines, you can bare it all without fear here. But please, for the sake of everyone around you, don’t act creepy and/or awkward. The best way to avoid being creepy is to lounge on Collins Beach in this:

Weird Things to do in Portland, Oregon: Hairy Swimsuit

While you’re there, don’t miss the Collin’s Beach UFO Boat, a strange old UFO-shaped boat abandoned and now covered in graffiti.


30. Soak Naked at Bagby Hot Springs

Bagby Hot Springs is a magical place tucked into the Mount Hood National Forest about two hours outside of Portland. An elaborate system of wooden aqueducts channels hot water into a collection of private and public soaking tubs hollowed out of old-growth timber.

As with most Oregon hot springs, Bagby is a clothing-optional soaking area. But be warned, the people exercising their right to exhibitionism are generally not the ones you would want to see naked.


31. Burn your Mouth on Wings at Fire on the Mountain

Head to one of Portland’s Fire on the Mountain locations, where you can test your limits with their super spicy El Jefe sauce. Prepare for your mouth to be on fire! 


32. Second-Hand Shop at Last Thursday on Alberta Street

Portland, Oregon: Weird & Unique Things To Do - Last Thursday on N. Alberta Street

First Thursday is an event in the Pearl district of Portland where posh people dress up to sip wine samples while browsing art galleries. Last Thursday on Alberta Street is almost the exact opposite. Grungy hippies fire dance in the streets, people dress up like gnomes, and stands selling bizarre art creations dominate the sidewalks. The last time I was there, I almost bought an action figure that had a dinosaur head on a superman body. Almost…

Grab an outdoor table at one of the bars near 20th street for some epic people-watching.

You should check out First Thursday too, but it’s not even a little bit weird.


33. Get Drunk at the Movies

There are quite a few second-run movie theaters in Portland where you can see movies that have been in theaters for a while at a fraction of the price. You can also purchase beer and wine at many of these. But the most popular venues in town belong to the McMenamins chain. You can count on them for good movies, comfy seating, piping hot pizza, and cold draft beer. It’s the perfect rainy day activity in Portland.


34. Light your Coffee on Fire at Huber’s

Established in 1879, Huber’s is the oldest restaurant in Portland. The restaurant is fine dining (i.e. expensive) but if you head to the bar in the back, you’ll find a more casual atmosphere and the best Spanish coffee in Portland.

The servers make quite a show out of preparing your coffee. They will bring a tray to your table, light things on fire, and pour the alcohol into your glass from way above their head. Get your phone out, you’ll want to record this! (and make sure you tip your server)


35. Dress up Like Santa for Santacon

Portland, Oregon: Weird & Unique Things To Do - Santa Con

If you find yourself in Portland during the holiday season, you’re in luck. Hundreds of people dressed as Santa meetup to begin a weird, drunken, debaucherous pub crawl known as Santacon. You’ll meet a ton of new friends and have an absolute blast!


36. Watch the Adult Soapbox Derby

Every year since 1997, Portlanders have been building coaster cars powered only by gravity to race down a hill at Mt. Tabor Park. It’s called the Adult Soapbox Derby and unlike some of the other things on this weird list, it actually IS fun for the whole family.

The car designs range from hilarious to extremely innovative and everything in between. Thousands of people gather to see the costumed teams competing for awards in speed, engineering, and other creative categories.


37. Drink a Beer While in Detention at the Kennedy School

Kennedy School was actually an elementary school in Portland that has been converted into a hotel, complete with a movie theater and several bars and restaurants inside. McMenamins renovated the abandoned school to create one of the most unique spaces in all of Portland.  Even if you don’t stay in one of the cute hotel rooms, it’s worth stopping by for a beer to check it out.


38. Bounce on the Dance Floor at the Crystal Ballroom

Portland, Oregon: Weird & Unique Things To Do - Crystal Ballroom

The Crystal Ballroom is a music venue in Portland that regularly has live performances by popular bands. The dance floor is what makes this particular space special. It’s spring-loaded so when the place gets crowded and people start dancing, the floor really starts to move. It’s like dancing on a mattress with 500 strangers.


39. Visit the Statue that Gave the Show Portlandia its Name

Portland, Oregon: Weird & Unusual Things To Do - Portlandia Statue

The Portlandia statue is the second-largest copper repoussé statue in the United States. What is the largest you ask? The statue of Liberty, of course. You’ll find the Portlandia Statue perched above the entrance to the equally quirky postmodern Portland Building on SW 5th Avenue.

The Portland statue is also a popular stop for most Portland Walking Tours.


40. Join a Bike Pub Crawl

If you can get some friends together on a sunny afternoon, BrewCycle is a fun way to see the city and check out some Portland breweries. Or you can sign up on your own and make some new friends! Either way, you’ll get some exercise while simultaneously getting a little drunk.

If you’re not into the idea of a “BrewCycle,” then you can always opt for a plain ol’ walking tour of Portland’s breweries.


41. Trade Books at a Tiny Community Library

There are cute little “community libraries” in neighborhoods all around Portland where you can take a book if you leave a book. The book choices generally aren’t amazing but the tiny libraries are pretty creative.


42. Shop for Books at Powell’s

Portland, Oregon: Weird & Unusual Things To Do - Powell's Book Store

If you can’t find the book that you’re looking for at the tiny community libraries, head to Powell’s Bookstore. With an inventory of over two million volumes, they are the largest independent bookstore in the world. The store actually occupies an entire city block! You can spend hours just wandering around, sipping coffee while browsing the impressive collection.


43. Sip the Creepiest Drinks in Town at Raven’s Manor

Part bar, part haunted house, part laboratory, Raven’s Manor touts itself as a “haunted manor-themed bar with an interactive mixology experience like no other.” Order up a “Deadly Tonic” or an “Eerie Elixir,” and if you’re hungry, the menu features horrifying dishes, like the Grubs in “Pest” O and the Steaked to Death.


44. Walk Across the No-Cars-Allowed Bridge

Portland, Oregon: Weird & Unique Things To Do - Tilikum Crossing

The Tilikum Crossing Bridge in Portland is the first major bridge in the US that was designed to allow access to public transit vehicles, cyclists, and pedestrians – but not cars. The architecture of it is really beautiful, no doubt you’ll spot it immediately from the downtown waterfront.


45. Go Zoobombing

There’s no question that Portland has an obsession with bicycles. But the Zoobombers take it one step further. Every Sunday evening they gather with their tiny tricked-out kids’ bikes, board the MAX (Portland’s light rail), and ride from downtown Portland to Washington Park station near the zoo. Then they coast down through the West Hills back to their starting point where they all pile back onto the MAX and do it over again.

If you want to join in the fun but don’t have your own set of miniature wheels, don’t worry. They keep a collection of loner bikes piled up at the corner of 13th and Broadway (affectionately known as the “Zoobomb Pile”).


46. Visit the Vacuum Museum

Since 1932, Stark’s Vacuums has been selling its namesake appliance and is one of the largest independent vacuum cleaner retailers in the country. But their real claim to fame is their oddball Vacuum Museum located inside of their flagship store on NE Grand Avenue in Portland. It used to house over 300 random pieces of vacuum-cleaning history but now the collection has been reduced to “25 of the most iconic and loved vacuums in history.”


47. Shop at Paxton Gate

Shopping at Paxton Gate is like wandering through your weird uncle’s study. If your weird uncle was 50% Charles Darwin and 50% Indiana Jones. You can pick up anything from a fossilized Tyrannosaurus Rex tooth to a human skull. For the ultimate weird Portland souvenir, inquire about their DIY taxidermy jackalope class.


48. Get “Laid” at a Tiki Bar

The Alibi Tiki Bar in Portland, Oregon


Portland winters can be long, wet, and gloomy. What better way to cure your winter woes than by sipping a fruity island cocktail while surrounded by tiki masks, taxidermied blowfish, and an indoor waterfall? Head to The Alibi Tiki Lounge to experience Portland’s most eclectic bar and most popular karaoke joint. There is no way you can miss the giant flashing neon sign as you’re cruising up Interstate Avenue.

If you’re heading to Portland in the winter, make sure you pack accordingly!


49. Drink at a Speakeasy

You’re liable to walk right past the Bible Club if you are strolling around SE Portland. From the outside, it’s a nondescript residential house with curtains drawn and no signage. But step through the front door and you’re transported to the 1900s by a secret speakeasy bar serving up creative cocktails to those in the know.


50. Check out the Zymoglyphic Museum

The Zymoglyphic Museum is a new entry to Portland’s ever-growing list of eclectic museums and attractions. It claims to be “the world’s only institution devoted to the study and display of art, artifacts, and natural history of the Zymoglyphic region”. It’s a collection of the creations that artist Jim Stewart put on display in a curio cabinet fashion.

It’s only open on the second and fourth Sundays of the month, but you can request a special viewing appointment by emailing the curator (AKA Jim) at zymoglyphic@gmail.com.


51. Play Pirate-Themed Glow-in-the-Dark Miniature Golf

Pirate-themed glow-in-the-dark miniature golf is a lot of weirdness to take in, but it really does exist. And the cherry on top is that Glowing Greens is hidden in the basement of a boring old QDOBA Mexican Restaurant in downtown Portland. Make sure you get a pair of their 3D glasses to really make the experience disorienting.


52. Sip Coffee with Some Spirits

While we’re on the topic of the paranormal, Rimsky-Korsakoffee is Portland’s most haunted coffee house. It’s in an old Victorian House in the Buckman neighborhood. Patrons believe that the tables occasionally turn, ever so slowly. So when you reach down for your cup of coffee it has mysteriously rotated away from your seat.

Make sure you use the restroom while you’re there for an extra surprise!


53. Eat a Donut-Centric Brunch at HunnyMilk

Famous for its set brunch menu, at HunnyMilk, you will choose a savory item, a sweet item, and a drink. This is Portland, so it’s no surprise that every dish here incorporates a donut in some form or another!

The “Savory” menu boasts an “Everything” Beignet Benedict with avo and crème fraîche hollandaise, the Cheezy Herb Biscuit Holes and Chorizo Gravy with spicy maple syrup, and the Popcorn Chicken and Waffle Donuts with truffle honey.

For the “Sweet” option, you can go for the Apple Pie Churro-Nut, the blueberry-stuffed Sourdough Pancake Donut, or the Strawberry Shortcake Bars with a rhubarb compote. Either way you go, the presentation makes everything almost too good to eat!


54. Pair your Wine with your Astrological Sign

Pairings Portland describes itself as “Portland’s weirdest wine shop and bar”. How can wine be weird you ask? Well, not only do they pair wine with food, but also with astrological signs, TV and movie characters, dog breeds, and songs. It’s a fun and approachable way to taste some wine and have some laughs while doing it!


55. Listen to the Acoustics at Pioneer Square

Weird Things to do in Portland, Oregon: Echo Chamber in Pioneer Square

Pioneer Square is the center of downtown Portland – both physically and socially – and is always full of Portlanders eating lunch, reading, and chatting with friends. But what many people (even locals) don’t realize is that the square contains a secret echo chamber. If you stand on the inlaid plaque at the center of the amphitheater on the Northwest corner (by the Starbucks), your voice will be amplified as if you’re speaking through a microphone.

While you are there get your picture with the famous “Allow Me” statue. He is more commonly known as “Umbrella Man” and is the most photographed man in Portland.


56. Smoke and then Sweat

Who doesn’t love to smoke a joint right before an aerobics class? Well, me, honestly. My preference is to devour a bag of Cheetos while watching Keeping up with the Kardashians. But if you do actually like to be productive when you’re high, then Mary Jane Fonda is the perfect class for you. DM them on Instagram for a class schedule.

So what are you waiting for? Get out there and start exploring Portland, you weirdos!


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Author

  • Valerie Wheatley

    Val grew up in Portland, Oregon but moved to Oahu on a whim back in 2013. She sold her house and all of her belongings and bought a one-way ticket. Since then she’s taken two around-the-world trips and has visited 60-ish countries while living out of a duffel bag.

    Val started documenting the Wandering Wheatleys travels back in 2013 as a way to update friends and family about her whereabouts and to relay humorous daily interactions. The only readers were her mom and her mother-in-law but that didn’t stop her!

    These days you’ll find Val dreaming up future trips, creating new travel content, managing a team of amazing travel enthusiasts, and chasing around her two adorable but naughty kids.

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