The ‘City of Roses’ and perhaps the hipster capital of the world is a desirable place to be with new and old blending seamlessly.

If you’re old enough to remember The Goonies, Oregon is bound to have a place in your heart; And Portland, Oregon is exactly as you might imagine it would be now the boys have grown up and are covered in tattoos, donning beards and nose rings, but still scooting around on skateboards.

With a vibe cool enough to freeze a chickpea ice cream (a real vegan thing at Little Bean), you might be surprised at the friendliness of the locals, who often break a smile underneath their uniform beanie and/or moustache, and even though medical marijuana is legal, I’m sure this is not connected! 

However, the reputation of being a hip and happening place doesn’t come without its prejudices from the locals. The influx of out of towners since the hipster boom in the 90s has pushed Portland natives further out to the suburbs, and artisan coffee shops, tattoo parlours and microbreweries with flamboyant names and ironic interiors, have forced residential rents up, so be sure to double check for bicycles as you wander around town!

However there is still a huge creative community, and the ‘City of Roses’ is a desirable place to be with new and old blending seamlessly. Split into two definite sides by the Willamette River, you can find Tudor, Victorian and colonial-style houses rubbing shoulders in the suburbs, with repurposed factories making the best use of space in the East; New-build eco-skyscrapers steal the limelight downtown, and industrial brick warehouses take prominence in the cobblestoned Pearl District.

Neighbourhoods are important, and you find locals eating, drinking and supporting their regular haunts, but it’s easy enough to jump in an Uber across town and try out the latest rooftop bar, brunch spot or veggie restaurant. But as a quick guide, Downtown is a mash-up of vintage boutiques, fusion cuisine, traditional diners, coffee shops, and hole-in-the-wall bars which attracts the very cool urban crowd. The Alberta Arts District is a little more upmarket and boasts classy art galleries and designer boutiques for those with more money, and 

SE Portland is a foodies heaven with alternative pizza joints, food carts an abundance of vintage, kitsch and New Age stores including the vegan mecca- a mini-mart, lifestyle store and tattoo parlour on one block. Whereas neighbouring Hawthorne represents the veggie dining options and retro stores. The Pearl District is perfectly located for walking around and taking in the sights; It also has lots of bars if you get thirsty on your travels.

However, off the beaten track, St. John’s, is what many locals claim Portland was back in the day– original dive bars, arty yet unpretentious boutiques, filled with no frills locals, who just happen to be very hip! 

And don’t forget the Farmers Market near the University, which takes place every Saturday. Mingle with the good looking locals and admire their homegrown goodies! 

Apart from food, Portland is a hub for arts and culture. Shamelessly proclaiming “Keep Portland Weird” on the side of a dive club, this has actually become the official city motto. However, there is a range of culture from the huge contemporary and indigenous art at the large and airy Portland Art Museum, which deserves at least half a day of anyone’s visit so you can truly embrace the large collection which fills three connected buildings.

Contemporary dance fans will love Portland’s Community dance centre Bodyvox; The warehouse space regularly showcases fresh, informed presentations designed to impress, entertain and make you think; Theatres are widely represented, with The Armory,  offering two stages, and taking pride of place in a stunning converted military unit, which is the epitome of Portland’s all-encompassing vision. The Portland Centre Stage at The Armory is the largest theatre company in the city, and the Artistic Director promises an eclectic mix of vigour, verve and vitality in all the shows, where the audience is so close to the stage that they almost become part of the play.

The Mission Theatre is also worth a visit, with its burlesque-inspired stage and mezzanine, this restored building draws fuses the olde worlde with eastern sensuality, and is a great place for a date night. For more underground shows, the Portland Center for the Performing Arts, puts on bargain music, dance and theatre performances, and is the starting point for many fringe performers.

But if you’re more of a groupie than a musicals fan, there are plenty of hipster hangouts for music, food and performance where you can get a dose of food and culture in one. If you fancy reliving your Breakfast Club days, Revolution Hall is the place to be. A converted high school which was restored after a fire in 1924, it is the home of many a hip roots, jazz or comedy night, which takes place in the main auditorium. With a beautifully renovated roof deck bar, it gathers crowds of beautiful people all year round. 

The city’s Crystal Ballroom is another hipster hangout, which unsurprisingly entertains a restaurant/craft brewery/club/music venue under one roof, along with the McMenamins pub and theatre, where you can drink beer whilst watching indie (natch) films. However, not everyone likes micro beer (or cider)…. Gin and whisky are making ripples with the influencers and cocktail bars are on the rise, and you can even sample local wine from nearby Willamette Valley, which has produced several fruity homegrown blends… 

Visitors to Portland will not come home empty handed, as shopping is encouraged as a sport! And each neighbourhood offers its own personality, with more than just the average shops. With an above average proportion of hip young things, it is no wonder that there is an excess of thrift shops and consignment stores. These aren’t like our Save the Children shops which you can find on your local high street, they are huge warehouses with items carefully colour co-ordinated and sized with precision, and Portlanders love them! If you are looking for high-end labels or have a penchant for the nineties, eighties or seventies, be prepared to roll your sleeves up and rummage! The stock is priced fairly, and shopping in Portland is tax-free. You can’t go wrong with Buffalo Exchange, which has several outlets across the city, but if you want to make a day of it, head to Hawthorne for a mixed bag of shops, where you are guaranteed to find something for all tastes, but it’s also good for designer homeware, Made in Portland goods and a great independent milliner.

Whatever your reason for visiting Portland, you can’t help but thrive on its cosmopolitan vibe; It is the perfect pitching spot for anyone with a sense of adventure, and the large liberal city embraces diversity, smoking pot and craft beer festivals in equal measure. You can source everything from skateboards to organic cotton t-shirts to personalised jewellery. The urban spaces and social media enhance Portland’s industrial appeal, and the constant nightlife, healthy living and craft beers do nothing to discourage the pre-baby spenders. 

Combined with Portland’s emphasis on self-expression the city is a breeding ground for many independent businesses and startups. But it’s not just an inner city destination, go in summer and you can be immersed in nature. Just two hours will transport you to two mountain ranges which are ideal for hiking, and the Pacific Ocean. It is also the home of one of the country’s largest parks taking up 5,000 acres and holds plenty of summer festivals.

Even the hotels are cool. The Jupiter ‘Next’ Hotel could easily be confused with a Kooples commercial, staffed by beautiful creatures; The sister hotel to one of Portland’s classics, the original Jupiter, which offers a more classic 60’s motel vibe next door, it has vamped up its decor and embraced the millennials, and it’s recent addition to SE Portland means it is kickstarting a renaissance of the area. With its adjoining bar-restaurant ‘Hey Love’ and the infamous ‘Doug Fir’ basement lounge, you won’t have to leave the neighbourhood! 

With an industrial feel, the rooms have a Scandi vibe and you can just hang out in social lounge space- set up for co-working as well as chilling, or enjoy the open air terrace on the upper deck for guests, you won’t actually need to leave the premises. But if you don’t have a MacBook Air and some wireless headphones, you will most definitely be in the minority…