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Best weekend and day trips outside of Portland, OR

The best guide for weekend and day trips outside of Portland, OR. Recommended Spots Central Oregon Central Oregon is one of my favorite parts of…

by  Emily

The best guide for weekend and day trips outside of Portland, OR.

Recommended Spots

  • Central Oregon
  • Columbia River Gorge
  • Oregon Coast

Central Oregon

Central Oregon is one of my favorite parts of the state. Whether you’re planning a weekend trip or staying for a week, you’ll find plenty to do. Between the mountain views, high desert landscapes, small towns, breweries, and endless outdoor adventures, it’s a destination you can visit any time of year.

Bend

If you’re spending a few days in Oregon, Bend is absolutely worth adding to your itinerary. Tucked along the eastern side of the Cascade Mountains, Bend has something to offer in every season.

In the winter, head to Mt. Bachelor or Hoodoo for skiing and snowboarding. During the summer, spend your days floating the Deschutes River, hiking, paddleboarding on one of the Cascade Lakes, or exploring nearby lava caves. After a day outside, grab dinner and a beer at one of Bend’s many local breweries. It’s hard to go wrong.

Where to Stay

If you’re looking for a resort, there are several great options with golf courses, pools, bike trails, restaurants, and plenty of activities for families.

Resorts

Hotels

Things to Do

Winter

  • Ski or snowboard at Mt. Bachelor
  • Spend a day at Hoodoo Ski Area
  • Walk around Downtown Bend and browse the local shops
  • Warm up with coffee or visit one of the many breweries

Summer

  • Float the Deschutes River through town
  • Hike at Smith Rock State Park
  • Drive the Cascade Lakes Scenic Byway
  • Spend the day at Sparks Lake, Elk Lake, or Devil’s Lake
  • Explore Lava River Cave
  • Watch the sunset from Pilot Butte
  • Rent a paddleboard or kayak
  • Visit a few local breweries

Where to Eat & Drink

There are so many great restaurants in Bend, but these are a few of my favorites:

For breweries, check out Deschutes Brewery, Crux Fermentation Project(my fave!), Bend Brewing Company, Sunriver Brewing, 10 Barrel Brewing, Goodlife Brewing, or Monkless Brewing.

Sisters

About 30 minutes from Bend, Sisters is one of the cutest small towns in Central Oregon. The downtown area is full of locally owned shops, art galleries, and cafés, making it an easy place to spend a few hours.

If you’re driving through, stop at Sisters Coffee Company for coffee or grab a milkshake from Sno Cap Drive-In. If you happen to be visiting during one of the town’s festivals or markets, it’s worth spending a little extra time exploring.

Redmond

Most people fly into Redmond and head straight to Bend, but Redmond is worth checking out too. It’s usually a little quieter, often more affordable, and has a growing food and brewery scene.

Spend some time walking around downtown, grab breakfast at Mo’s Egg House, or stop by Initiative Brewing after a day of exploring. Smith Rock State Park is only about 20 minutes away, making Redmond a great place to stay if hiking or rock climbing is at the top of your list.

Don’t Miss Nearby

If you have extra time, there are a few places around Central Oregon that are worth the drive.

  • Smith Rock State Park has some of the best hiking in Oregon, with incredible views of the Crooked River and towering rock formations.
  • Tumalo Falls is an easy stop just outside of Bend and one of the area’s most beautiful waterfalls.
  • Newberry National Volcanic Monument is home to lava flows, volcanic landscapes, Paulina Lake, and miles of hiking trails.
  • The Cascade Lakes Scenic Byway is one of the prettiest drives in Oregon, especially during the summer and early fall.
  • The Painted Hills are about two hours from Bend and make a great day trip if you have the time.

No matter when you visit, Central Oregon is the kind of place that’s easy to fall in love with. You can spend the morning hiking, the afternoon on the river, and end the day with good food and a local beer. It’s one of those places that makes you want to plan your next trip before you’ve even left.

Columbia River Gorge

Hit the Trails

Whether you’re looking for a challenging hike or an easy walk with incredible views, the Columbia River Gorge has plenty to choose from.

  • Dog Mountain is one of the area’s most popular hikes, especially in late spring when the hillside is covered in wildflowers. It’s definitely a workout, but the panoramic views from the top are worth every step.
  • Hood River to Mosier Trail is a much more relaxed option. This paved trail follows the Columbia River and is perfect for walking, biking, or enjoying sunset views.
  • Coyote Wall is another favorite, with rolling hills, wildflowers in the spring, and some of the best views of the Gorge.
  • Wahclella Falls is a short hike that leads to a beautiful waterfall tucked inside a canyon.
  • Multnomah Falls is a must if it’s your first time visiting the Gorge. Go early in the morning to beat the crowds.

Where to Eat & Drink

After a day outside, Hood River is the perfect place to refuel. Whether you’re craving pizza, burgers, tacos, or a craft beer with a view, you really can’t go wrong.

Some of my favorites are:

Don’t Miss

One of my favorite ways to spend a day around Hood River is driving the Hood River Fruit Loop. Depending on the season, you’ll find blooming orchards, U-pick fruit, lavender fields, wineries, cideries, farm stands, and mountain views around almost every corner. It’s one of those drives where you’ll want to stop every few miles.

A few can’t-miss stops include:

If you’re visiting in the fall, this area is especially beautiful. Between the changing leaves, apple orchards, pumpkin patches, and views of Mt. Hood, it’s hard to beat.

Oregon Coast

If there’s one road trip you have to take while you’re in Oregon, it’s the Oregon Coast. Every beach town has its own personality, and no matter where you stop, you’ll find rugged cliffs, wide sandy beaches, sea stacks, fresh seafood, and incredible sunsets.

The northern coast is perfect for a day trip from Portland, with most towns less than two hours away. If you’re heading farther south, I’d recommend making it an overnight (or even a weekend) trip so you have time to slow down and explore.

Here are a few of my favorite stops along the coast.

Cannon Beach

Cannon Beach is probably the most recognizable spot on the Oregon Coast, and for good reason. It’s home to the iconic Haystack Rock, one of the most photographed landmarks in the state. While it can get busy, it’s absolutely worth visiting at least once.

Spend some time walking the beach, browse the cute downtown shops, and if you have time, head over to Ecola State Park for some of the best coastal views in Oregon. If you’re visiting during low tide, keep an eye out for tide pools around Haystack Rock.

Where to eat

Manzanita

Just 20 minutes south of Cannon Beach, Manzanita is one of my favorite small beach towns. It’s quieter, a little less crowded, and has a long stretch of beach that’s perfect for a walk. If you’re looking for a slower pace, this is your spot.

Take a stroll down Laneda Avenue, browse the local shops, grab a coffee, and enjoy the beach without the crowds.

Where to eat

Pacific City

Pacific City feels like the classic Oregon Coast town. It’s smaller than Cannon Beach but has some of the best views on the coast. Cape Kiwanda, the giant sand dune, and the offshore Haystack Rock make this one of my favorite places to spend a day.

If you’re feeling adventurous, climb the sand dune for an incredible view of the coastline. Then head down to watch the surfers or the famous dory boats launch right from the beach. It’s something you don’t see every day.

Where to eat

Newport

If you’re making your way down the coast, Newport is one of the best places to spend the night. There’s enough to do here that you can easily fill an entire weekend.

Walk around Nye Beach, explore the local shops, grab coffee, or spend an afternoon on the sand. Head over to the Historic Bayfront to watch sea lions lounging on the docks, browse the shops, or book a crabbing or fishing trip.

Families will love the Oregon Coast Aquarium, and don’t miss Yaquina Head Outstanding Natural Area or Yaquina Bay Lighthouse while you’re in town.

Where to eat

A Few More Coastal Favorites

If you have extra time, these towns are also worth adding to your itinerary:

  • Seaside for the classic boardwalk, arcade, and family-friendly atmosphere.
  • Depoe Bay for whale watching. During migration season, there’s a good chance you’ll spot gray whales right from shore.
  • Yachats for dramatic coastline, tide pools, and easy access to Cape Perpetua.
  • Lincoln City for shopping, glass floats, and miles of sandy beaches. If you’re lucky, you might even find one of the hidden hand-blown glass floats along the shore.
  • Gearhart for quiet coastal charm, historic shingled cottages, and wide-open, uncrowded beaches. If you wander down to the shore at low tide, you will find miles of sand practically paved with intact sand dollars.

No matter which towns you visit, don’t be afraid to pull over at the scenic viewpoints along Highway 101. Some of the best views on the Oregon Coast aren’t planned. They’re the random beaches, overlooks, and roadside stops you stumble across along the way. That’s part of what makes this stretch of coastline so special.