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The Big American Road Trip. An idea that had been simmering in my mind for some time now. I’d mapped a decent part of California, braved the thundering New York subways, got lost while solo adventuring in Arizona, soaked myself in the Florida sunshine and partied hard in Boston. So where to next in the weird and wonderful United States of America? Craving a dose of nature, be it mountain air or seascape (preferably where the blue of the ocean mirrored the political stance of the destination in question), my attention turned to Oregon. A jewel of the Pacific Northwest, Oregon is home to some of the most sublime natural vistas on the planet, where rugged shorelines meet dense forestry, desert panoramas and snow-capped mountain ranges. That, combined with my deep-rooted love for homegrown creativity and film (with countless classics shot in the state), sealed the deal. Before you ask, “What about Trump?” relax - Oregon is pretty much as Democratic as they come. Just a week before I arrived, Portland staged a cheeky (literally), rebellious naked bike ride, with stars like Benson Boone pedalling in protest. With a landscape large enough to fit the UK inside, Oregon offers so much to explore that a touch of politics won’t overshadow its natural beauty and vibrant culture. With eight days on the road and 900 miles behind the wheel, it was easy to see why Oregon is a mecca for cinema buffs, nature enthusiasts, athletes, artists, liberals and anyone yearning for adventure. From thrift stores to wineries, coffee shops and haute hotels, discover the ultimate cool-girl guide to Oregon below. Portland, Oregon’s largest city, prides itself on being, well, different. You’ll likely see signs reading ‘Keep Portland Weird’ plastered on shop windows, the unofficial slogan of the humming metropolis. And joyously weird it is. While downtown maintains a steady rhythm, areas such as Hawthorne vibrate on a higher frequency. Independent coffee roasters (oh, how I long for the electrifying kick of that coffee), unmissable thrift stores, witchy apothecaries, quirky book shops and breweries culminate in a vibrant scene dominated by left-leaning inhabitants that champion queer culture loud and proud. The city has a distinct counterculture, boasting a colourful vintage scene, a thriving LGBTQ+ community and even theatre groups recreating The Rocky Horror Picture Show for live audiences. Weird and wonderful indeed. Where to stay Woodlark Hotel The Woodlark Hotel, which sits in downtown Portland, is an airy, modern hideaway for both locals and visitors alike. Dine at Bullard, the hotel’s Texas-inspired restaurant that marries West Coast flair with Southern hospitality or kick back with a cocktail in hand at Abigail Hall, a cosy, 40-seater bar that offers delectable snacks and elegant tipples. With gargantuan, cloud-like beds that were a sight for sore eyes following a ten hour flight and welcoming staff, the hotel made for the perfect stay while battling the initial stages of pan-Atlantic jet lag. Where to shop 2nd Street A few minutes down the road from The Woodlark lies 2nd Street - my forever favourite thrift spot. This gem of a consignment store is bursting with valuable finds. From Vivienne Westwood to Prada, Ralph Lauren to Marc Jacobs and so much more, the shop is always top of our list to visit when we return to the US. Be sure to visit the larger sister store in Hawthorne, which left our wallets empty and our suitcases full. Roots & Crowns Founded by Max Turk, a self-professed Jewish Queer Plant Witch, Roots & Crowns is a small batch apothecary located in Nob Hill which is absolutely not to be missed. From natural lilac-infused perfumes to botanical skincare, herbal remedies and more, the shop is brimming with unique products that satisfy all of the senses. Tender Loving Empire Tender Loving Empire was founded by Brianne and Jared Mees - then two creatives fresh out of college, obsessed with handmade art and the people behind it. What started as rogue concerts and pop-up art shows in abandoned spaces grew into a full-fledged company. In 2006, the pair landed in Portland with a shoebox of savings and an idea: to build a community where creativity thrives. Nearly two decades later, Tender Loving Empire spans seven stores, represents hundreds of makers, and continues to champion art, music, and connection. Step inside to uncover the cutest Oregon-themed gems, from keyrings to gourmet chilli jams, artworks, cards, jewellery and more. After all, when it comes to Oregon, local is king. Founded in 1932, Danner offers heritage-driven performance footwear that marries rugged American craftsmanship with modern engineering. With full-grain leather, Vibram soles, and a robust recrafting service, Danner boots are built to endure uphill adventure, work, and everyday style alike - hence why the brand was the first port of call when fashioning Reese Witherspoon’s hiking boots in Jean-Marc Vallée’s 2014 film Wild. The Trail 2650 in Oil Green/Jet Black came home with me. Crossroads Another secondhand hub to explore, Crossroads in Hawthorne is saturated with stellar thrift finds. From designer labels like Acne Studios and Wales Bonner to Oregon-born sportswear brands such as Nike, the large store is filled with epic, well-priced pieces to bag. Where to drink & dine Fools & Horses Lose yourself in the low strum of the double bass at Fools & Horses, a cocktail bar and kitchen in northwest Portland. Offering a neat selection of innovative cocktails (I highly recommend the Blossom) in addition to jazz night (hence the strings), the cosy, low-lit spot is primed for date nights and girly get-togethers. Pop into sister bar Pink Rabbit next door for round two. Blends Juice Bar Kickstart the day with a seriously good acai bowl at Blends Juice Bar. Topped with berries, desiccated coconut, granola, bananas and a generous lick of honey, these fruity feasts are the primed for health and wellness enthusiasts craving a sweet start to the morning. Stumptown Coffee Roasters Oregonians like their coffee strong - meaning you’ll likely be bouncing off the walls for a good few hours after one sip. Founded in Portland by Duane Sorenson in 1999, Stumptown Coffee Roasters is a mainstay - sourcing exceptional coffee from the world’s finest farms, forging transparent farmer relationships, and roasting with obsessive (and delicious) attention to detail. Never Coffee Lab A charming spot for your mid morning caffeine top up, Never Coffee Lab is the proud formulator of ten signature latte blends - with the Yuzu Salt Latte proving to be a popular pick. Featuring notes of yuzu fruit, sansho pepper and burnt sugar with coconut cream, the unexpected blend is a treat for the senses. The aptly titled Oregon Latte was a personal favourite, marked by notes of Cascade hops, dulce de leche and locally-produced Jacobson sea salt. Where to explore Portland Japanese Garden Craving a corner of quiet away from the city? Head to the Portland Japanese Garden and bask in the beauty of the serene retreat, featuring winding paths, moss-covered stones, flowing streams, and framed by views of the city. Founded on the principle of cultural harmony, the garden is celebrated as one of the most authentically Japanese landscapes beyond Japan’s borders. Explore the romantic Rose Garden, pay a visit to the resident Koi fish and watch in awe as the cascading waterfalls tumble before you. For more information about Portland, please visit travelportland.com. Now, it’s time to hit the road. Film lovers, make sure to download the SetJetters app before you go - it’s your guide to discovering the countless iconic movie locations worth stopping for along the way. Included in the mix is St. Helens, a pretty little spot where you can find Bella Swan’s house from Twilight (topless, tree-scaling Taylor Lautner not included, apologies) and the set of the Disney Channel classic Halloweentown. Then onto Astoria. Located in the northwest corner of the state, the town is famous for its cameo in The Goonies. Visit The Goonies’ iconic house and the Oregon Film Museum - set in the historic Clatsop County Jail, where the movie’s opening jailbreak was filmed. Small but mighty, the museum celebrates Oregon’s rich cinematic legacy, offering behind-the-scenes stories and stills from the many films shot across the state. Wander through the building, which was a working jail from 1914 to 1976, and uncover mini sets where you can record your own film clips with friends and most importantly, spy both One-Eyed Willy surrounded by treasure and Data’s techy costume. Pinchers of Power and all. Astoria is also home to a handful of kooky stores to peruse. Be sure to stop into Weird Sisters Freak Boutique, a quirky, underground shop selling curious costumes, fish slippers, vintage pieces and costume jewels, plus Garbo’s Vintage Wear for a classic jumbled thrift experience. For those wanting a more contemporary shopping experience, head to Hello Doe for natural beauty products, gifts and more. Before heading back to The Norblad for the night, a hotel that sits just moments away from galleries, breweries, and the Columbia River waterfront in downtown Astoria, be sure to grab a pint at Bridgewater Bistro before hitting the hay. The next morning, walk to Sleeper Coffee for a strong brew while overlooking the shimmering azure waters that stretch to the shores of Washington. Ecola State Park, Cannon Beach & Newport Next stop - Newport. Wanting to gain the full Goonies experience, it was vital we stopped at Ecola State Park en route to visit the set of the Fratelli’s hideout. Safe to say, the park defied our expectations. While the fictional building was taken down after the film wrapped, visitors can soak up stunning panoramic views of the wild Oregon coastline, marked by large, rugged rocks and swathes of white sandy beaches. These postcard panoramas are bolstered by several hiking trails to explore, yet most are reserved for experienced hikers only. As you wind up the forested roads to the start of the trails, be sure to take in the ethereality of the sky-kissing pines and rich emerald greenery of the magnificent nature spot. A short drive from Ecola State Park is Cannon Beach. Steeped in sea-salted air, Cannon Beach is a must-see coastal town with picture-perfect views. Often cited as Oregon’s best beach and named after a naval cannon that washed up after a shipwreck in the 1840s, Cannon Beach is home to the iconic Haystack Rock - which undoubtedly cropped up on your ‘For You’ page when scrolling through TikTok for pre-Oregon trip inspiration. Stop here to marvel at the sweeping shore and make the most of a breathtaking photo opp. Finally, Newport. While the town itself doesn’t have a huge amount to offer, it provided one of the best hotel experiences of the whole trip. Hotel Sylvia carved out a moment of calm we craved after a jam-packed start to our Oregon adventures. Nestled on the cliffs of Nye Beach, the historic and freshly‑renovated hotel evokes a quiet literary retreat by the sea. With 22 themed rooms celebrating authors and genres, the oceanfront hub delivers with unmatched seascape views, while cosy reading nooks and nods to storytelling invite you to disconnect, reflect and simply soak in the coastal calm. Also, extra points for the delicious breakfast. Somewhat begrudgingly, we checked out of the charming Hotel Sylvia and once again, hit the road - this time setting our sights on Ashland. En route, stop at the Heceta Head Lighthouse to stretch your legs (if time allows) and glimpse the wildlife seeking refuge on the shore. Belt up for a long yet near-transcendent four hour drive ahead of you. Be sure to go south on Highway 101, then east on Highway 38 through the Umpqua River Valley for the most awe-inspiring views spanning dramatic coastlines to fairytale woodlands, iridescent serpentine rivers, rolling valleys and more. The drive will forever be etched in my mind, thanks to the spellbinding landscapes that unfolded before us. If time (and tolerance) allows, stop for a winery lunch in the Umpqua Valley. The valley is one of Southern Oregon’s most diverse growing regions, where the fruitful environment and mild climate produce more than 40 grape varietals from Pinot Noir and Tempranillo to Viognier and Malbec. Eventually you’ll reach Ashland - the town which serves as inspiration for Laika’s 2009 dark fantasy horror Coraline. One of my favourite films, Coraline follows the story of a feisty young girl who stumbles upon another, more sinister, world within her home. Stop-motion fans will immediately recognise the sweet, earth-toned storefronts, flanked by fiery autumn trees that epitomise the beauty of ‘fall’ in the US. Tourists typically pay a visit to Ashland to attend the world-famous Oregon Shakespeare Festival, which is also referenced in the spook-tastic film. Ideal for literacy lovers. After a brief stroll in Lithia Park, which has an undeniable hippie feel to it, head to your reservation at Cocorico for one of the best meals of your life (no exaggeration here - the Marionberry pie is to die for.) The neo-rustic kitchen, helmed by Chef Nat Brosi, is absolutely not to be missed. Inhale the zesty freshness of the apple and arugula (rocket for my British readers) salad, followed by the chickpea tagine topped with rose harissa, turmeric, dried blueberry and mushroom crisp, before indulging in a warm slice of Marionberry magic finished with a dollop of vanilla ice cream. Wash it down with the Marionberry Lemon Drop, crafted with Wild Roots Marionberry vodka, cointreau and fresh lemon. Heaven. Head back to the Ashland Springs Hotel to nurse your food baby and replenish your energy following a long day of driving. Located just a 20 minute drive from the Californian border in downtown Ashland, the historic landmark is a spacious, vintage-inspired establishment complete with grand architecture and a playfully kitsch feel. Crater Lake & Bend Set an early alarm because you’re off to Bend. Get up and grab an on-the-go brekkie from Mix Bakery (10/10 carb-loaded yum-factor) before jumping in the car and heading north to Crater Lake. Crater Lake National Park, perched atop Southern Oregon’s Cascade Mountains, is a year-round wonder of deep blue waters, sheer 2,000-foot cliffs, and volcanic history. Formed 7,700 years ago when Mount Mazama collapsed, the caldera reaches depths of 1,943 feet - the deepest in the US Rim Drive. The park’s dramatic landscapes offer hiking, skiing, and a living classroom of natural beauty - but be sure to check which driving routes are open before visiting as this can vary. Bend was one of my favourite stops and offered up a more lively scene than prior towns visited. Situated in the high desert of Central Oregon, the town is lined with independent boutiques, restaurants, cafés, bars and breweries and surrounded by epic nature from mountains to volcanoes. Bathed in desert sunshine and framed by ponderosa pines and open grasslands, the city sits just 20 minutes from the majestic Cascades. Once called ‘Farewell Bend,’ this riverside town offers 600 miles of mountain biking trails, 800 ancient lava caves, and Mt. Bachelor’s 4,300 acres of skiable slopes. When winter snow blankets the peaks, locals hit the slopes en masse - making the most of the 360-degree skiing experience the mountains have to offer. Summer brings lazy floats down the Deschutes, with a whitewater park and even a manmade surf wave that perfectly encapsulates the town’s outdoorsy soul. Shopping enthusiasts can meander through the Old Mill district and enjoy the Keratin Dreams cocktail at Lady Bird Cultural Society after a day of skiing, fishing, hiking, biking or golfing. A civilised alternative to La Folie Deuce with no drunken ski home required. Bend’s storybook charm has long drawn in an eclectic cast of characters. Among its more notable past residents are George Putnam - New York publishing heir, former mayor, and husband to the ill-fated aviator Amelia Earhart. The town’s cinematic allure hasn’t gone unnoticed either: Wild captured the serenity of Paulina Lake in the nearby Newberry Volcanic National Monument, while Swordfish, starring John Travolta, spotlighted the dramatic cliffs of Smith Rock State Park - the birthplace of American sport climbing and another must-see stop on your travels. For the adventure seekers, it's time to layer up because tonight, you’re one with nature. Pre-book the Moonlight & Starlight Canoe Tour with Wanderlust Tours to marvel at the sights and sounds that nighttime in Central Oregon has to offer while paddling under the milky way (yes - the actual milky way.) This is a one-of-a-kind experience - made even better by the utterly badass yet considerate guides who lead you through the activity with calming ease and supply you with hot chocolate and snickerdoodle cookies to keep energy levels up. Take a moment to pause and reflect under a blanket of twinkling stars before hopping back in the van, shedding the thermals and whacking the heating right up. Roll into bed at The Oxford Hotel - a dreamy, celebrity-approved stay in downtown Bend and the town’s first and only luxury boutique hotel. Boasting 59 spacious and luxurious executive suites, many with views of the Cascade Mountains, the hotel conjures up sleek serenity with its modern interiors, airy rooms and hospitable staff. The next morning, be sure to head to Sparrow Bakery for a hefty hit of sugary goodness. Locals will insist you drop in for the famed Ocean Roll, glazed with sticky cardamom and puffed to perfection. It’s well worth it. Bid farewell to both the diet and the lovely Oxford Hotel and set off for Mt. Hood with some scenic stops along the way. For more information about Bend, please visit visitbend.com and visitcentraloregon.com, Mt. Hood & Timberline Lodge Perched high on the slopes of Mt. Hood, Timberline Lodge & Ski Area is something of a living legend - and the only ski destination in North America open all year round. With the 2021 addition of Summit Pass, the resort now boasts 4,540 feet of vertical terrain, the longest continuous descent in the United States. From crisp November mornings to toasty summer days, Timberline’s Palmer Express lift keeps the snow dreams alive well into September, drawing pros and beginners alike. The main draw of the stop? Timberline Lodge’s striking exterior famously starred in Stanley Kubrick’s The Shining, standing in for the eerie Overlook Hotel. While the interiors were filmed in Colorado, the lodge’s spooky façade and snowbound setting captured the film’s haunting, isolated atmosphere. Today, it remains a pilgrimage site for both cinephiles and Shelley Duvall sympathisers. Hood River and Multnomah Falls Throughout our trip, locals kept telling us about how much we’d love Hood River - and they weren’t wrong. The tiny town is one of Oregon’s crown jewels, beloved by young families and avid windsurfers alike. Pristinely curated secondhand stores such Ice Cream For Crow Vintage (we found vintage Dior - it was major) and the diddiest Goodwill you will ever lay eyes on nod to its youthful energy, while pFriem Family Brewers and Ferment Brewing Company embrace the town’s homegrown spirit. Speaking of, visitors can take part in the Hood River Valley Fruit Loop, a 35-mile self-guided journey through orchards, wineries, breweries, cideries, and flower fields, where 28 farm stands showcase the valley’s rich agricultural heritage and bountiful pears, apples, and cherries. Afterwards, grab a table at Celilo - a refined yet relaxed dining experience that celebrates Pacific Northwest cuisine made with seasonal, locally-sourced ingredients. Book in at the Hood River Hotel, a downtown retreat built in 1911 and now one of the town’s most beloved vintage haunts. Expect vibrant art‑filled interiors, turntables in the rooms, and a homely vibe that nods to the past while offering all the comforts you’d want today. If you’re planning on circling back to Portland, drop in to see Multnomah Falls - Oregon’s tallest waterfall. Standing at 620 feet, the waterfall is a breathtaking natural wonder just a short drive from the city. Cascading in two tiers, the falls are framed by lush Pacific Northwest forest, with the iconic Benson Bridge offering a perfect vantage point for photos. Easily accessible via a scenic trail or from the highway, Multnomah Falls enchants visitors year-round and understandably so. An itty-bitty spot with oodles of small-town charm (a hallmark of Oregon) Hood River captures the state’s spirit perfectly: locally-made, effortlessly beautiful, and full of friendly faces (and most importantly, golden retrievers.) If London’s humdrum ever gets too much, you’ll know where to find me. It’s near-impossible not to be romantic about Oregon. It may lack the sun-drunk dreaminess of California and the pulsing buzz of the East Coast, but its homegrown, off-beat energy and epic stop-dead-in-your-tracks scenery is unlike anything I’ve experienced before. For those seeking the ultimate adventure, the kind you’ll be telling your kids about one day with misty-eyed wonder, Oregon is calling. In short, I’ve never said ‘wow’ so many times in such a short span - whether at a “rad” view or something utterly bonkers witnessed in Portland. If that doesn’t make you book a flight, I’m not sure what will. For more information or to plan your trip, visit https://traveloregon.com
