Oregon holidays

Holidays to Oregon are for exploring the kind of jaw-dropping landscapes you only find in the Pacific Northwest. There are dense evergreen forests, raging waterfalls and wild, windswept beaches perfect for storm watching. But to truly dive headfirst into this fertile region, spend a little time in Portland, whose rugged, independent spirit has produced some of the most exciting restaurants, breweries and bars in the country.

Top destinations in Oregon

Cannon Beach

From breathtaking sunsets over Haystack Rock to hikes through mossy rainforests, see why this charming coastal town deserves a place on your Pacific Northwest itinerary.

Portland

Oregon’s hippest city has never looked better, with cutting-edge galleries, next-wave breweries and access to some of the best urban parks in the United States.

Medford

Tucked into the ruggedly beautiful Rogue Valley, southern Oregon’s largest city is a great base for outdoor adventures, from skiing to hiking and lavender picking.

Oregon: fast facts

Language

English

Currency

United States dollar ($)

Time zone

Portland - UTC−8 (PST) and UTC−7 (PDT)

High season

June – September

Low season

November – March

We scan 100 billion prices, so you don’t have to

Compare prices to bag a cheap holiday to Oregon

Book your holiday to Oregon, all in one place

Oregon holiday highlights

Oregon
Brand USA

See Crater Lake

A trip to Crater Lake is one of the best things to do in Oregon. Perched atop the Cascade Mountains, the deepest lake in the US is also one of the clearest. Experience this picturesque playground at your own speed at Crater Lake National Park. Hike over 160 kilometres of trails, hop on a trolley tour, or take a zip line for a bird’s eye view.

Drive the coast

Take an unforgettable road trip along scenic Highway 101, which hugs Oregon’s misty coastline. You’ll see historic lighthouses, like the one in Yaquina Bay, which boasts an intact 1870s residence. Stop at Netarts for oysters on the half shell, and tour the famous cranberry bogs in Bandon. In Hammond, check out the shipwreck of the Peter Iredale, still decaying where it ran aground in 1906.

Go wine tasting

Oregonians take their adult beverages seriously. Head to the Willamette Valley to tour vineyards (there are more than 800 of them) and sample some of the best pinot noir and chardonnay in the region. Prefer grain over grapes? There’s no better place to explore Oregon’s booming brewery scene than outdoorsy Bend, an early adopter of the country’s thriving craft beer movement.

Things to do in Oregon

Oregon
Brand USA

Top attractions

Experience Oregon’s wild beauty on the Trail of Ten Falls in Silver Falls State Park, where waterfalls tumble through mossy forest. On the coast, visit the Neskowin Ghost Forest to see centuries-old tree stumps emerge eerily from the sand. And no place better embodies the spirit of Portland than Powell’s City of Books, the largest independent bookshop in the world.

Beaches

Just 90 minutes from Portland, Cannon Beach is one of the most iconic beaches in Oregon. Massive Haystack Rock, featured in the movie ‘The Goonies’, juts from the water, a symbol of the state’s 583 kilometres of coastline. Resort town Seaside boasts a bikeable oceanfront promenade and a carousel. In Florence, the expansive Oregon Dunes reach to the Pacific Ocean.

Nature

Experience Oregon’s natural beauty at Columbia River Gorge, a 1,200-metre-deep river canyon where you’ll find the stunning Multnomah Falls. Nearby ski spot Mount Hood is home to glaciers and snowfields. Looking to relax? Seek out one of the dozens of natural hot springs in the state, like Terwilliger Hot Springs in the Willamette National Forest.

Cuisine

Some of the best restaurants in Oregon are on four wheels. Portland’s sprawling food cart scene serves up everything from fried chicken to sushi. Find them in pods throughout the city. Portland also has a collection of inventive doughnut shops. On the coast, look for fresh fish, oysters and Dungeness crab. Newport, with its bustling fish market, is a prime spot for seafood.

Culture and museums

Visit the best museums in Oregon in its cultural capital, Portland. Explore Native American carvings, 19th-century landscape paintings and more at the Portland Art Museum. Tour a submarine or stargaze inside the planetarium at the Oregon Museum of Science and Industry. Theatre fans should head to Ashland for the annual Oregon Shakespeare Festival, which presents modern works alongside those by the Bard.

Nightlife

Portland boasts the liveliest nightlife in Oregon. Head to the Pearl District, where you’ll find wall-to-wall craft breweries alongside some of the best cocktail lounges in the Pacific Northwest. The city also hosts standout performance spaces like Crystal Ballroom and Revolution Hall, a former high school turned music venue that channels vintage charm with a modern edge.

Find the best time to visit Oregon

Weather in Oregon through the year

March – May: Expect wet weather throughout Oregon in spring, when the state explodes in fresh greenery and colourful blooms. Put on your walking shoes and stroll sites like Portland Japanese Garden at their most verdant.

June – October: While summer nights (and even some days) can still be chilly, these are the region’s warmest and driest months. It is also Oregon’s fire season — monitor any active wildfires and heed safety warnings, especially when hiking and camping.

November – February: Rain and fog dominate the coast in winter, while snow falls in the higher altitudes. This is the best time to visit Oregon to hit the slopes.

Events in Oregon

Bend Winterfest (February): One of the top winter events in Oregon, this multi-day festival transforms Bend into a snowy playground. Highlights include skiing and snowboarding competitions, ice carving displays, fire pits, live music and local food vendors — all set against the scenic backdrop of the Cascade Range.

Oregon Shakespeare Festival (March to October): Held in the charming town of Ashland, this celebration of the Bard presents fresh takes on classic plays alongside modern ones like Stephen Sondheim’s ‘Into the Woods’.

Portland Rose Festival (May to June): Portland bursts with colour and creativity during this beloved tradition, featuring quirky parades, fireworks, dragon boat races and citywide celebrations.

Know before you go

Budget

You don’t have to work too hard to have a cheap holiday in Oregon, especially if you visit in the cooler months. You’ll usually find great value eats at food trucks in the cities. An inexpensive meal will cost about 18 US dollars ($). A domestic beer is around $7, and a cappuccino is under $5. A short cab ride will run you about $10.

Health and safety

Oregon’s a great place to explore, but a little prep goes a long way. Pack layers — the weather can shift quickly, especially in the mountains and along the coast. Stay on marked trails, keep wildlife at a distance, and never leave valuables in your car. In summer, check for wildfire updates and follow any local restrictions.

Free things to do

Explore the Portland Art Museum’s vast collection of over 50,000 works — free to visitors under 17 and to all on first Thursdays. Then head outdoors to one of Oregon’s admission-free state parks, including the breathtaking Silver Falls State Park, where forest trails lead to the 54-metre South Falls (parking fees may apply if driving).

Family friendly

Visit McMinnville’s Evergreen Aviation & Space Museum to see the world’s largest wooden plane, then cool off next door at Wings and Waves Waterpark. In late summer, head to Salem for the Oregon State Fair, packed with rides, fried treats and farm fun. For year-round adventures, check the state parks calendar for kid-friendly events like birdhouse building.

Getting around Oregon

Portland
traveloregon.com

Public transport

Buses: Oregon’s POINT bus system is an affordable option that connects major cities, rural outposts and transit hubs like Amtrak. Private coaches, such as Greyhound and FlixBus, also operate throughout the state.

Trains: Amtrak operates two scenic routes in Oregon. The Amtrak Cascades has stops stretching between Portland and Eugene, while the Coast Starlight stops in Klamath Falls.

Boats: Three ferries operate in the Willamette Valley, providing short crossings along the Willamette River. They’re popular with cyclists accessing rural backroads but also carry motorcycles and cars for convenient transport across the water.

Domestic flights

If you’re short on time, skip the scenic drives and hop on a domestic flight to reach areas throughout the state. Oregon’s major hub is Portland International Airport, which is a destination in its own right. You’ll also find regional hubs in Eugene, Klamath Falls and just north of Bend.

Find domestic flights

Driving and car hire

With 29 scenic byways, Oregon is best explored by car. Major hire companies operate throughout the state, making it easy to find a vehicle. Check road conditions before heading out in winter, and carry snow chains if advised, especially when driving through mountain passes or remote areas.

Check car hire

FAQs about Oregon holidays

For urban vibes surrounded by lush greenery, start in artsy Portland. If you’re more in the mood for wine tasting and rural luxury, post up in the Willamette Valley. Bend is the place to be in winter if you love snow sports.
If you only have a long weekend, base yourself in Portland and plan at least one day trip to a nearby site like the Columbia River Gorge or the Willamette Valley. Stay five days or longer for a more comprehensive experience, like driving the Oregon Coast.
The summer months are the best time to visit Oregon for beach walks and outdoor adventures. If you don’t mind rain, aim for winter, when rates dip. The ski season usually begins in November and can extend through May. The autumn harvest season is ideal for vineyard tours — and it’s a good time to see the leaves change colour.
Oregon is a safe place to travel, but be careful when heading for the outdoors. Be aware of wildfire advisories, and follow posted guidelines and staff advice when visiting parks and beaches.
English is the most widely spoken language in Oregon, followed by Spanish. In East Portland, you'll also hear Vietnamese, reflecting the area's large Southeast Asian community. While English is dominant statewide, Oregon’s cultural diversity adds a range of languages to the mix, especially in urban areas.
You’ll use US dollars ($) in Oregon. Banks, currency exchanges and ATMs can easily be found in cities and even many rural areas. Tipping is common, and a 20% gratuity for good service in a restaurant is normal. Plan on dropping around $5 a day for hotel cleaning staff.