8 incredible things to do on a Portland holiday

When you arrive in Portland, you’ll most likely want to spend your first day getting a lay of the land. Simply taking yourself for a wander is a fantastic ‘thing to do’, but if you want that extra dose of local insight, we recommend joining an organised tour. The Pink Trolley City Tour of Portland is a popular choice, taking you on a scenic ride and stopping off at the famous International Rose Test Gardens. Or, you could discover the city by bike on a guided cycling tour, discovering some quality food and beer finds along the way.

If you enjoy spending time outdoors, Oregon’s Mt Hood Territory is a must-see during your Portland holiday. Alongside the namesake snow-topped mountain, here you’ll find lush valleys, glossy lakes, and boundless rivers and streams. Whether you fancy getting sweaty on a challenging trek, racing along wooded biking trails, or kayaking across the tranquil water, this is the place to go. And, if you want to get a bit closer to the area’s flora and fauna, why not visit the Tualatin River National Wildlife Refuge or enjoy a bike ride on the Tualatin Valley Scenic Bikeway?

One of the many things Portland has to boast about is its incredible farm-to-table dining scene. While there are a number of places you can head to if you want to experience this for yourself, the Tualatin Valley and Mt. Hood Territory are great starting points. Enjoy an intimate, al-fresco dinner at one of the region’s picturesque vineyards and indulge in a wine-paired tasting menu that celebrates the delicious local produce. Alternatively, be sure to check out the famous food cart pods that dot the region for some mouth-wateringly good street food. Or, if you’re staying closer to the city centre, check out Kann, named the 'Best New Restaurant in America' for 2022 by Esquire Magazine.

No matter what season you choose to visit Portland, you’re bound to be blown away by this city’s natural beauty. And what’s great is that you don’t have to travel far to connect with nature, thanks to the abundance of parks and green spaces in and around the Central City district. The Portland Japanese Garden is a particularly peaceful spot you can visit year-round, with its gently cascading waterfalls and maple trees that blaze red in autumn. Or, if you’re planning a holiday between May and October, you’ll be able to see the International Rose Test Gardens in full bloom.  

If you consider yourself a bit of a night owl or simply enjoy making the most of your evenings out when you’re on holiday, then you’re in for a treat, as Portland’s buzzing atmosphere extends well past sunset. You could watch some theatre, opera or ballet at one of the city’s top venues – many of which are encompassed by Portland’5 Centers for the Arts. Alternatively, keep it casual and catch a live music gig. Whether you opt for an underground jazz improv session, an indie rock concert, or a high-capacity festival, you’ll always find something to suit your taste.  

Dubbed the ‘craft beer capital’, Portland is known for taking its beverages pretty seriously. There are over 70 breweries scattered across the city, and – in our humble opinion – it’s worth popping into at least one or two during your stay! Join a group tour to meet some fellow beer enthusiasts, or go solo and follow the Mt Hood Territory Tap Trail. Another fantastic option is to stay in Portland’s famed Tualatin Valley, known for its top-class wines. Check out the Tualatin Valley Scenic Vineyard & Valley tour route and visit one (or more) of the wineries or tasting rooms, sampling the signature tipples.

For all the thrill seekers thinking about a Portland holiday, High-Flying Adventures in the Tualatin Valley or Mt. Hood Territory should definitely be on your radar. From nail-biting ziplines and daring treetop adventures to epic glider plane flights over the rolling landscape - there’s plenty here to get your heart racing. Having a go at any one of those activities will have earned you a glass of wine at the local vineyard, but if you want to up the adrenaline even more, there’s always the option to swap your sauvignon for a skydive - freefalling from over 14,000 feet on a tandem jump.

Whether you’re shopping for yourself or on the hunt for a souvenir for a friend or family member, you’ll unlikely come back from your Portland trip empty-handed. After all, there’s no sales tax in Oregon, so you’ve got a good excuse for that extra little indulgence. If it’s luxury goods you’re after, you’ll want to make your way down to Pioneer Palace, the city’s main upscale shopping mall. Then, you can spend some time exploring some of the locally-owned boutiques and second-hand vintage shops. And, if you’re in the city on the weekend, make sure you don’t miss the Portland Saturday Market.