What can I say… I love the Pacific Northwest. Yes, it rains, and yes, it’s cloudy, but there are endless number of things to do and see! Literally-pick a direction and drive! I have created a list of long weekend ideas from Portland that you can check out too!

1) Crater Lake
This is definitely a place to check out- Crater Lake looks so surreal it shouldn’t exist! Check out my weekend guide for Crater Lake here!

2) The Wilamette Valley

Long weekend ideas from Portland don’t actually have to be hours away… The Wilamette Valley is commonly referred to as “Oregon Wine County,” and is about one hour away! There are over 600+ wineries to choose from and such little time so how does one even know where to start?! Though there are a plethora of options, Oregon’s climate makes for a splendid Pinot Noir. When recommending wineries, I always look at view and atmosphere, as well as food/snack availability. Beware that wine tasting is rarely the “$10 a tasting now” as most wineries as for $20+ a tasting, so doing three a day adds up!

My general suggestion would be:
Saturday: Willakenzie, Gran Moraine, Stoller
Sunday: Archery Summit, White Rose Estate, Domaine Serene
Monday: Detox and hike Hike Trail of Ten Falls at Silver Falls State Park. Unfortunately, most of this trail is not dog friendly, but you can hike certain small sections with dogs.

3) Walla Walla

I know you’re probably thinking, Walla Walla what? This is a city that many people have never heard of but deserves your undivided attention! Downtown Walla Walla is very walkable and a great place to stay. Walla Walla has some amazing breakfast places and wineries, which is a huge plus in my book!
Day 1: Start your morning with Bacon and Eggs or Maple Counter Cafe. After, head over to Lewis and Clark State Park to spend time in the swimming holes. Next, check out Whitman College architecture and the sculpture park. At the end of the night, finish your dinner at Saffron Mediterranean Kitchen.
Day 2: Start your morning with Maple Counter Cafe, and make sure you fill up on food here, because next on the itinerary is wine, wine and wine! After breakfast, tour The Blue Mountain Cidery & Visit The Taphouse, then, drive to Tranche and enjoy the views, wine and firepit! Finally, after hours and hours of wine tasting, end your night at Passatempo Taverna for some amazing pasta.
Day 3: Lunch at Graze and head back to Portland

4) Seattle
Check out the itinerary here!

5) Olympic National Park
Check out the itinerary here!

6) Smith Rock & Bend
Bend is an AWESOME choice, no matter what time of year and is perfect for all ages, fitness levels and families. During the winter you will find many places to ski and snowshoe, and during all other seasons you will find a plethora of mountain biking, hiking, shopping, restaurants and fall in love with this small town! Some options include: visiting one of the many breweries, hiking
Hiking Suggestions: Tumalo Falls, Green Lakes Trail (permit required), or if you into mountaineering or advanced hiking; South Sisters‘ trail (permit required)!
I would then set aside one entire day for Smith Rock State Park, with the most popular hike being Misery Ridge. Smith Rock is said to be the Yosemite of Oregon and a sacred place for many hikers.

7) Alvord Hot Springs & Steen Mountains
Firstly to note, the Steen Mountains are one of the most remote places in Oregon. Deep in Southeast Oregon sits the Steen Mountains. you will have no service and limited restaurants and gas stations, so this trip will need careful planning with prep work and navigation. This is a word class destination many people seek out for camping, remote backpacking, fishing and hunting. From Portland, you will drive towards Bend, and 2-3 hours yonder you will find the city of Frenchglen, the entrance of the Steens Mountain Wilderness Area.

One iconic thing to do in Steen Mountains is Steens Mountain Loop Road. After camping underneath dreamy stars, spend time hiking Kiger Gorge Overlook and Wildhorse Lake. Finally, the Alvord Hot Springs are also 30-40 minutes away and another tourist attraction but keep it on the down low so it maintains its beauty!

8) The Wallowas
The Wallowas are said to be the Switzerland of Oregon. However, I am not going to lie, when driving on the freeway it’s hard to see why it’s considered the “Switzerland of Oregon.” To really understand you need to be IN the Wallowas wilderness! Hiding in Eastern Oregon, you will see ghost towns which were previously gold mining settlements, farmlands with scenic mountains as the backdrop, glacial lakes, and the beautiful Eagle Cap Wilderness.

My recommendation would be a backpacking trip in the Wallowas, such as Mirror Lake via Two Pan Trailhead. However, I know that is not everyone’s cup of tea, so if you don’t feel like scaling a mountain, then there are many more options. Firstly, take the tram! The Wallowa Lake Tramway can take you up to Mt. Howard. Here, you can spend two hours exploring the views of the rolling hills and Hells Canyon. After the tram, take a scenic road trip around the Wallowas on the beautiful Hells Canyon Scenic Byway. Lastly, I would suggest staying in Joseph, a city with a cute artsy downtown and art gallery, as well as a stellar view.

9) Sunriver

Like the resort life in the mountains? Then Sunriver is for you! Whether you are looking for a cozy getaway or a long weekend filled with adventure, there are endless options in this majestic city.
Day 1 Hit the Trails: There are endless amount of walking trails that you must explore on your first day! No matter where you stay, guaranteed there will be a hike within 10 minutes. Finally, to top the night off, drive over to the Oregon Observatory on River Road to check out the stars! This observatory has over 10 telescopes and a learning center where you can soak in all the astrology facts.
Day 2 Lava Caves and Sunriver Resort Marina: Visit the Newberry National Volcanic Monument which has an underground point, the Lava River Cave. Here, you will be in a 1.5-mile portion of a cave that is open for self-guided tours. Be sure to bring a flashlight and a jacket as it can chilly underground. After exploring the cave and getting your fix of Indiana Jones, head over the Sunriver Resort Marina and check out all the water activities they have!
Day 3 Tumalo Falls and more Sunriver: Start the day the Sunriver Nature Center, followed by Sunriver Village. The Nature Center is a great place for families as there are interactive activities for children. The Sunriver Village is an open mall and awesome for all ages with activities ranging from craft beer to fine arts. Finally, before heading home check out the impressive 97-foot waterfall at Tumalo Falls!

10) Medford-Ashland
Known for its world class theater, wine regions, outdoor adventure, outdoor scenery and more- Ashland is for you! You may have heard of Ashland from your high school class when studying Shakespear, but I promise you don’t just have to visit for the Shakespear Festival! If you do choose to go for the Shakespear Festival, expect theatrical magic!
Day 1: On your way into town, feel free to stop in Medford, 20 minutes before Ashland, and get one more city checked off your list. In Medford, you can check out the downtown & the Village at Medford. Once, you have gotten antiques and shopping off your list, head to Ashland! You will find miles of hiking trails in Lithia Park.
Day 2: Check out Siskiyou Mountain Park – Parks Division – Parks and Recreation – City of Ashland, Oregon and Chozu Bath and Tea Gardens. Depending on what time you are done with this, save time for drinking at one of the wineries! Check out a list of more restaurants and wineries here.
Day 3: If you have it in you, check out my itinerary for one day in Crater Lake! This is definitely a place to visit, but it does make for an exceptionally long day!

11) Columbia River Gorge & Hood River

Similar to the Wilamette Valley, long weekend ideas from Portland don’t actually have to be hours away…within one hour on the 84 you will see so much beauty you won’t know where to start! One of my favorite day and weekend places to check out! I can never get enough of the drive along the 84 as there are numerous hikes, waterfalls, scenic vistas, restaurants and things to do for all ages! A good starting place of places to check out would be:
First Day: Vista House, Multnomah Falls, Columbia River Gorge, Beacon Rock, Hood River and Rowena Crest Viewpoint!
Day 2: Start your morning hiking Coyote Wall and then drive the famous 35-mile road called the “The Fruit Loop” filled with wineries, breweries, lavender fields and farms.
Last Day: Hood River is additionally known for its world class windsurfing, or any other water sport such as paddleboarding, kayaking and rafting! Spend the day in the water with some lessons!

12) Oregon Coast- Astoria, Seaside & Cannon Beach, Manzanita

13) Leavenworth

Leavenworth is SOOO dreamy and will keep you coming back for more! This is by far a personal favorite as it is accommodating for all ages and interests. I personally love it for the rad mountains and plethora of wineries and breweries! Leavenworth is worth visiting in every season. In the summertime, you will find a numerous amount of hikes, in the fall time you will find golden larches everywhere, in the springtime you will find rafting, in the wintertime you will find dreamy twinkly lights with horse carriages. You could spend days just walking around the town, floating the river, and exploring the city park.
My favorite hiking options would be: Colchuck Lake (get here EARLY), Minotaur Lake & Icicle Ridge Trail
Favorite food options: To be honest, it is quite hard to find a decent place to eat in Leavenworth if you are vegetarian or vegan, but when in doubt… there is a Mexican restaurant locally in town, Los Camperos! Leavenworth is primarily known for its bratwurst and pretzels which can be found practically everywhere. There is also Rudloofs Pizza, which is good for most diet types!
Favorite drinking places: Silvara Cellars, Blue Spirits Distilling & Bergdorf Cellars (bergdorfcellarswine.com)

I hope you enjoyed this list of long weekend ideas from Portland! Have anymore you want to add to the list? Feel free to message me!

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