So you’re thinking about a trip to Oregon? Good choice. It’s the kind of place that creeps up on you. One minute you’re wandering through rose gardens in the city and the next, you’re sipping wine with mountain views or standing in front of a waterfall that looks like something off a postcard.
And that’s just the start.
This itinerary is perfect if it’s your first time here. Solo trip, couples getaway or a fun group holiday — this itinerary gives you the best mix of city, nature and local gems.
You can also check out my guide on how to have an epic first trip to Chicago for more ideas if you’re planning a first-time city adventure.
We’re starting in Portland and ending with those ‘wow’ nature moments Oregon does so well.
From flower festivals to food carts, mountain drives to vineyard sips — here’s how to explore Oregon properly the first time around.
Portland Rose Festival
If you’re planning to explore Oregon in late spring, don’t miss the Portland Rose Festival. It’s more than just a floral parade.
It’s marching bands, street food, rides and a full-on celebration of Portland pride.
The Grand Floral Parade is the main event, but don’t skip CityFair at Tom McCall Waterfront Park. There are carnival rides, live music and plenty of family-friendly fun.
If you time your trip right, you’ll see Fleet Week too — when Navy ships dock in the city and open their doors to visitors.
Check out my complete guide to the Rose Festival Parade. 
It’s the kind of atmosphere you remember for years. Full of energy, full of colour and a great intro to the city.
Explore Oregon’s Gardens
To properly explore Oregon’s natural beauty, start small with Portland’s famous gardens. The International Rose Test Garden is tucked inside Washington Park and smells as dreamy as it looks.
With more than 10,000 rose bushes, it’s best visited in bloom (May to October).
Nearby, step into the Japanese Botanical Garden, one of the most authentic outside of Japan. Peaceful ponds, miniature landscapes and perfect photo backdrops.
Whether you’re into gardens or not, both are worth a stroll. Quiet, calming and close to the city centre.
These two spots are perfect for unwinding after the buzz of the Rose Festival.
Pittock Mansion and Lan Su Garden
From flowers to historic flair. Pittock Mansion sits on a hill with sweeping views of Portland and beyond. This stately home gives you a glimpse into Portland’s past.
Take your time walking through the restored rooms.
Then, head downtown to the Lan Su Chinese Garden, a traditional Suzhou-style garden in the middle of the city. You’d never know you’re a block from the busy streets once you’re inside.
With covered walkways and reflective pools, it’s one of Portland’s hidden gems.
Take your camera and take your time — both places are slow travel at its best.
More Amazing City Spots
If you love books (who doesn’t?), you’ll love this next stop. Start with a wander through Powell’s Books, the largest independent bookstore in the world. It’s huge. Floors of every genre imaginable.
Grab a coffee inside and then head out for something sweet. Voodoo Donuts is Portland’s most famous treat stop. Expect quirky shapes, bold colours and sugary overload. The line is usually long, but it moves fast.
Later, grab a drink at Midtown Beer Garden, home to 25+ food carts. From tacos to Thai, there’s something for every craving. Great people-watching too.
Downtown Finds
If you’re exploring downtown Portland, pop into Tea and Threads by Barnes and Morgan. It’s a calm, welcoming space where you can sip expertly brewed teas while browsing hand-stitched textiles.
This small business is all about thoughtful living and craftsmanship — a lovely stop if you like to support local makers.
Just a short walk away, Orox Leather Co. is another gem, offering handcrafted leather bags and accessories made right here in the city.
Both are perfect for picking up something meaningful, stylish and built to last.
Hawthorne Boulevard
Over in Southeast Portland, Hawthorne Boulevard is where things get delightfully eclectic.
This is the spot for quirky boutiques, vintage treasure troves and independent stores with real character. It’s relaxed, creative and full of colour — just like Portland itself.
Can’t-miss stop? Cubo de Cuba. Grab a plate of Cuban comfort food, sit outside and soak up the local buzz. It’s casual, tasty and hits the spot between shops.
Afternoon Tea and Night Bites in Portland
In the afternoon, treat yourself to high tea at Abigail Hall. This vintage-style bar in the Woodlark Hotel does a lovely selection of teas, savoury bites and cake stands that feel like a special occasion.
Later, head to The Flock Food Court for something more casual. With options from pizza to Korean BBQ, it’s a lively place to kick off your evening.
Still not done? End the night with a drink at the Bellpine Bar at the Ritz Carlton. The cocktails are fantastic and the views just as good.
Other places for a great lunch are Luc Lac Vietnamese Kitchen — fresh, quick, and full of flavour.
For dinner, book a table at G-Love, one of the city’s hottest spots. Their farm-to-street food concept is unique and the vibe is spot-on.
Ebiking and Waterfalls
Once you’ve soaked up Portland’s culture, it’s time to hit the great outdoors.
Head east to the Columbia River Gorge and try biking through the Columbia River Gorge — it’s one of the best ways to take in the scenery without tiring yourself out.
The route winds through forests and along cliff edges with amazing views over the river.
Don’t miss Multnomah Falls — Oregon’s tallest and most photographed waterfall. It’s an easy stop, and the viewing platform puts you right in front of the cascading drop.
This stretch of the state is ideal for adventurers. Hiking trails, lookout points and hidden gems — a perfect way to explore Oregon beyond its cities.
You can catch the real beauty of the falls here.
Tualatin Valley Wine Tour
For a slower day, head out with Good Vibes Tour with Shane. This small group tour takes you through the Tualatin Valley, just outside Portland.
It’s home to some of Oregon’s best wineries.
You’ll visit Ruby Vineyard, Raptor Ridge, and Ponzi Vineyards, where you can sip Pinot Noir and snack on cheese boards with vineyard views.
It’s relaxed, fun and a great way to explore Oregon’s wine scene without the crowds.
Shane keeps the tour light and personal — ideal if you want something a bit more local.
Coastal Nostalgia in Astoria
If you’ve got a couple of days to spare, make your way north to Astoria, one of Oregon’s oldest towns. This charming port city is packed with maritime history, great seafood and views over the Columbia River.
It’s also a must-visit for 80s movie fans — Astoria was the filming location for The Goonies. You can even walk past the house where Mikey and the gang kicked off their adventure.
Don’t miss the Oregon Film Museum, housed in the old Clatsop County Jail, which was used in the opening scenes of the film.
Add in scenic hikes, cosy cafés and a laid-back coastal vibe, and you’ve got another brilliant side to explore in Oregon.
Where to Stay in Oregon
Before heading out to explore the countryside, book a few nights at the Woodlark Hotel in downtown Portland.
It’s central, stylish, and has everything you need within walking distance.
Then, for a more peaceful stay, spend a night or two at Sosta House in wine country.
It’s a modern bed and breakfast with thoughtful touches, lovely hosts and the kind of calm you didn’t know you needed.
Both options give you two very different Oregon vibes — city cool and rural retreat.
Explore Oregon Your Way
There’s no wrong way to explore Oregon, but this itinerary gives you a taste of the very best.
Start with Portland’s creative buzz. Wander through gardens, browse indie bookshops and eat your way around the food halls.
Then head out for wide-open landscapes, waterfalls and wine country calm — the parts of Oregon that really stay with you.
From ships docking at the Rose Festival to cliff-edge views in the Columbia River Gorge, every stop shows you something new.
Oregon’s easy-going, welcoming and full of good surprises.
Leave space for slow mornings, spontaneous detours and the joy of discovering somewhere unexpected. That’s how you really get to know Oregon — one moment at a time.
If you’d like to explore more of the USA, head here.
