The Very Best of Oregon

Oregon is my all time favorite state. Although it’s not as famous as its neighbor to the south, there are no shortage of gems to discover in this nature-rich state. Oregon caters to a variety of tourists; nature lovers, beach goers, beer enthusiasts, theater fans, and that doesn’t even begin to scratch the surface of what Oregon can offer.
Over the next 7 days I will take you on my ideal vacation through the state and suggest activities and tips that I hope you find useful.
(This article may contain some affiliate links).


(Otter Crest Beach, courtesy of @oysterdork)

Day 1


The first stop on my ideal vacation would be Portland, Oregon, which is the largest city in Oregon. It’s known for its greenery, quirky citizens, amazing eats and inspiring the Emmy award-winning series, Portlandia. One thing I love about the downtown area of Portland is the compactness and how walkable it is (seriously, check out the downtown walkability score!)

Even though I’m someone who generally loves major cities (New York City, Los Angeles, Seoul, etc.) one thing that you won’t find in those places is a sense of calmness amongst locals and their warm demeanor. That’s not to say that any of the places I mentioned aren’t capable of those qualities, but rather the locals in Portland seem to take more time to enjoy their surroundings and shun corporate culture. The “rat race” culture is nowhere to be found, which could be attributed to the nature-focused peaceful lifestyle many citizens have.

Historic Landmark City of Portland Oregon Old Town Sign
Historic Landmark City of Portland Oregon Old Town Sign

(The iconic Portland Oregon sign courtesy of Deposit Photos).

If you love books, you MUST hit up Powell’s City of Books. As the world’s largest independent bookstore, Powell’s prides itself on remaining a success despite competition from mega companies like Amazon and Barnes & Noble. This four-story shop is so large it literally covers an entire block and houses approximately 1 million books. I already own way too many books for my own good, but as far as addictions go I figure owning books isn’t too bad of a habit to have. Personally, my favorite genres are travel and autobiographies.

pasted image 0 (8)(Image courtesy of Powell’s Books)

An undeniable fact about Portland is that it is foodie heaven. Vegans, carnivores, omnivores and everyone in between can easily find something that will not only suit their palate but leave them craving for more.

A few reasons could be attributed to why the food is so dang good. The proximity to the ocean allows people to eat the freshest caught seafood. In some towns fish is caught and prepared that same day. Additionally, the state is fortunate enough to have fertile, moist soil that makes an ideal environment for growing produce that can thrive.

One restaurant that stands out is Pok Pok. Pok Pok was founded by Andy Ricker, a chef who trained in Northern Thailand and brought the cuisine to the Pacific Northwest. This isn’t your run of the mill Pad Thai or green curry joint. As someone with Northern Thai ancestry it makes me overjoyed to see dishes I grew up with on a menu be made accessible to Americans. Items like som tum and khao soi rarely get the attention they deserve, which is a shame because these foods were staples when I was growing up and I wish everyone could try them. If his name sounds familiar chances are you watched him and Anthony Bourdain on Parts Unknown, trying out local cuisine in Chiang Mai, Thailand.

51890441_297918110888111_1520524464592957281_n(Khao soi noodles, photo courtesy of @pokpokpdx)

Day 2


A trip to Portland wouldn’t be complete without spending time in nature. Growing up in the Pacific Northwest has left me spoiled for beautiful scenery and lush forests. There are endless opportunities to explore the outdoors in Oregon but for the sake of this article I would recommend you spend your time in Forest Park, which has over 80 miles of trails. While entrance to the park is free, you must adhere to the park rules and be mindful of your surroundings. This means not staying past the 10pm closing time and keeping your dog on a leash at all times.

If you’re more of a garden person, I recommend visiting the Portland Japanese Garden. My favorite time of year is spring when cherry blossoms are in full bloom. In fall you can enjoy lovely views of red, yellow and orange foliage.

Here are the admission fees straight from the site:

Adult: $16.95
Senior (65+): $14.50
Student: $13.50
Youth (6-17): $11.50
Child (5 and under): Free
Members: Free

Waterfall at Portland Japanese Garden in Oregon Panorama
Waterfall at Portland Japanese Garden in Oregon Panorama

Activities in Portland:

Family friendly- For families with young children, Playdate PDX is the perfect option for indoor fun. It’s a giant indoor playground for kids that also allows parents to relax and socialize while their kids have fun. One really nice thing about Playdate PDX is that after 5pm on Mondays admission is FREE, which is great for families on a budget. Adult admission is always free, on weekdays children ages 3 and under only pay $4 and children 4 years and older have a fee of $8. You can check up to date prices here.

Teen friendly- What teen doesn’t love an amusement park? For the adventurous types I’d suggest going to Oaks Amusement Park, located south of downtown Portland. Activities you can enjoy at the park include roller skating, mini golf, rides, and a variety of games. The park is only open for a limited time (spring to late summer-with the exception of the roller rink, which is open year-round). Activities range from .25 cents up to $41. You can check prices here.

Adult only- A must do activity for adults in Portland is Pedalounge. What is Pedalounge? Basically it’s a pub crawl on a large, collective bicycle. You pedal together with a group to go from bar to bar. No drinking is allowed on the actual bicycle (although this rule is exempt in some other cities). This highly-rated activity is great for bachelorette parties, birthdays or even just to sight see around Portland. At time of writing it cost $26 per person. You can book a session here.

Day 3


The next destination on the list is Bend, Oregon, located about 3.5 hours southeast of Portland. Bend is an adventurous town that packs a lot of punch. Many of my friends go to Bend to snowboard and ski at Mount Bachelor.

Mt Bachelor ski park near Bend Oregon
Mt Bachelor ski park near Bend Oregon

(Mount Bachelor in winter, courtesy of Deposit Photos)

I prefer outdoor activities in spring and summer. If I had a free day I’d hike South Sister. It’s a challenging hike and at 9.5 hours you know you’re going to be absolutely exhausted afterwards. As the third highest mountain in Oregon you can’t expect it to be easy, right? If you want to read a first hand account on conquering this summit, here is a blog post detailing one hiker’s experience.

A seemingly endless field of lava leads out to the Sisters near Bend Oregon
A seemingly endless field of lava leads out to the Sisters near Bend Oregon

(Three Sisters Mountain, courtesy of Deposit Photos)

Day 4


I’m not gonna lie, after a day of strenuous activity there’s nothing more that I want than a cold pint of beer. The only issue is choosing an establishment when there are about 22 breweries. That’s why I would want to book a tour with Beer Me Bend Brewery Tours.

Activities in Bend:

Family friendly- If your family loves to golf then Widgi Creek is up your alley! Amenities include a 18 hole championship course,13,000+ square feet of putting green and 5,000+ square feet of chipping green.
Rates start at $29, more info here.

If museums are more your thing then check out High Desert Museum. High Desert Museum offers interactive exhibits that explore the nature and cultural history of Central Oregon. Two exhibits that will guarantee to intrigue your family are the Autzen Otter Exhibit and Donald M Kerr Birds of Prey Center (in this center you can see a golden eagle, horned owl and other fascinating species).
Rates vary, depending on season: General admission starts at
$17, with Senior rates at $14. Additional rate information here.

Teen friendly- If your teen is a water baby they’ll love SHARC (Sun River Aquatics & Recreation Center). They have tubing, water slides, hot tub and disc golf (not water-related but still fun).
General admission starts at $16. More rates here.

Adult only- Do you love good beer? If so, chances are you’ve heard of Deschutes Brewery. Their beers are sold across the globe and taste delicious as well. If you want to know how this brew is made, I would recommend booking a tour with them here
(link is for 21+ only).

Day 5

Crater Lake

From Bend, Oregon I’d drive 2 hours south to Crater Lake. I’ve been to Crater Lake three times but I keep coming back because its beauty is unparalleled. Not only does the beauty make it enjoyable to look at, there’s also other interesting reasons as to what makes this lake unique. Enjoy my mini list!

It is the deepest lake in the U.S.
It’s Oregon’s ONLY national park.
The island in the middle of the lake is called Wizard Island and you can actually hike it!
There is no inlet or outlet to the lake.
There is a famous stump in the lake known as “The Old Man of the Lake”.

Activities in Crater Lake:

The main attraction in Crater Lake is, well, Crater Lake. It’s an attraction suitable for all ages but if you have young children please be mindful of them being near any ledges close to the lake and viewpoints.

While the lake is technically open year round, some entry points are closed due to heavy snowfall (because of the elevation there is always at least some snow at Crater Lake). The best time to visit is between July-September, when all the roads and facilities are open. If you visit Crater Lake I recommend bringing lunch as the lunch at the Crater Lake Village is pricey and honestly not too appetizing. Costs at time of writing range from $20-$55, depending on the type vehicle and pass you want to get. More info on Crater Lake can be found here.


(You won’t regret traveling to see this view, promise. Image courtesy of Deposit Photos)

Day 6


The last stop on my ideal Oregon vacation is Ashland, Oregon. Ashland is home to the Oregon Shakespeare Festival, Lithia Park, and Southern Oregon University. I first discovered this charming town in high school, when I went on annual theater trips. I quickly fell in love with the shops and general vibe of the town (I also just really love banners).

Not to mention, the town has cute establishments such as the Tudor Guild Gift Shop (complete with Shakespeare head lollipops!) and Oberon’s Restaurant & Bar (an excellent place to grab a pint!)

Ashland, Oregon – September 30: People walking to the shops with vehicles parked on the streets. September 30 2018, Ashland, Oregon

(Image of downtown Ashland, courtesy of Deposit Photos)

When I go to Ashland, a free activity I enjoy is taking a stroll through Lithia Park. The trails are easy and the scenery is peaceful (especially if babbling brooks are your thing).

After going to the park I like to window shop at local establishments. Ashland has a large variety of shops to satisfy everyone’s shopping needs. Here’s a directory of current shops around town. My favorites are The Music Coop and Renaissance Rose.

Day 7


On my last day in Ashland I would definitely go see a play. The actors chosen for OSF are always top notch and trained at reputable academies. My favorite play I saw at OSF was “Vietgone”, a story about the play director’s parents and their story about falling in love at a refugee camp in Arkansas. It sounds like a sappy love story but I was laughing through most of the play as it was not set up as a tragedy, but as a tribute to the director’s parents’ journey. If it happens to be performing near you I would recommend it 100%.

Activities in Ashland:

In terms of activities, I always recommend going to the Oregon Shakespeare Festival, which takes place between March to October. Two things I love about the OSF: The intimacy of the theaters and the diversity, not only in terms of play genres but with the actors involved. At the time of writing this post, there is a show being put on about a Cambodian rock band

Some shows may have a limited runtime, so I’d recommend checking dates and booking early to secure a spot.

Other activities in Ashland:

Family-friendly- Scienceworks is a hands on museum that is enjoyed by family members of all ages. They have year round and temporary exhibits to keep things fresh and interesting at the museum. Kids have the chance to learn about painting, music, anatomy and a variety of other fascinating topics.
Hours of operation: Tuesday – Sunday, 10AM-5PM.
Admission cost direct from the site
$10.00 for kids ages 2-12
$12.00 for teens and adults
$10.00 for seniors 65+
Free for children under 2

Teen friendly- Teens can get their hearts racing by participating in exciting activities through figuring out clues at Escape Ashland. There are a few scenarios you can choose from, including a saloon or an audition theme. Games can accommodate 2-8 players. Larger groups should contact the company directly to discuss special arrangements.

Prices directly quoted from the site, “The Audition – Groups of 2: $40 adults, $35 students; groups of 3-5 $30 adults, $25 students; groups of 6-8 $28 adults, $23 students. We offer military discount the same as student discount.

The Ramblin’ Rogue – Groups of 2: $45 adults, $40 students; groups of 3: $35 adults, $30 students; groups of 4-5: $30 adults, 2 $28 students; groups of 6-8 $28 adults, $25 students. Military discount the same as student.” (, 2019). Complimentary cold drinks are included in the price.

Adult only- Head to Jackson Wellsprings to satisfy your sauna and spa cravings. This getaway located just outside Ashland is the perfect location to get some TLC.
Facilities include natural hot springs, private tubs, sauna, camping and even a Ladies Night. Some evenings are even clothing optional (please check here for more info). Cost is $10 for adults/$8 for seniors. Seasonal passes are available. More info here.


The best way to see Oregon is via car. Larger cities such as Portland and Eugene do have some public transportation options like trams and buses, but just like the majority of the U.S. the most reliable method of transportation is having a private car. You can rent them at establishments such as Enterprise, Avis, or Budget.

To Pump or Not to Pump

If you drive a car in the U.S. you’ve probably heard about Oregon’s unique law that forbid drivers from filling up their own cars with gas. As of writing this piece in 2019, this is the latest information I can find regarding the most recent pumping laws (disclaimer-I’m not a legal representative, laws regarding pumping are ongoing).
According to KGW8, citizens are exempt from this law if their vehicle only accepts diesel. Additionally if you have a motorized scooter you are allowed to pump your own gas. Lastly, populations of >40,000 are typically allowed to pump their own gas but in major towns such as Portland and Eugene you are still likely to encounter an attendant who will pump your gas for you.


In Oregon there are accommodation opportunities for every budget. From camping to staying in luxury hotels, the choice is yours. My preferred booking website is, where I’ve not only booked hotel rooms but even cruise ship vacations as well.


-Oregon is stunning year round but the ideal time to visit is between June-September, when the weather is most pleasant. Check with to plan your trip accordingly.

-Oregon has countless festivals and fairs throughout the year. My personal favorite is the Oregon Country Fair near Eugene that takes place every July. The only way I could describe it is part Renaissance Fair, part circus and part Burning Man. Easily the best part of the fair is the people-watching, as many fair attendees love to ham it up for the camera.

-Yes, Oregon has a reputation for being rainy. While Portlanders may shun raingear that doesn’t mean you should come unprepared. My preferred rainproof wear comes from Columbia but other brands should be fine as long as there’s a strong outer shell.

-One major attraction of Oregon I didn’t get to cover is the Oregon coast, which is an absolute must see on a trip to Oregon. I’ve been fortunate enough to go on a road trip all the way from Brookings to Astoria via the 101 coastal route, which is home to some of the most pristine beaches in the U.S. If you’d like to ask further questions about traveling along the Oregon coast, please contact me here.

Author bio:

pasted image 0 (9)Laura K. Sayles works as a virtual assistant online and travel planner. Her travels have taken her through 17 states, 37 countries (and counting). She has also lived overseas in New Zealand, Thailand and South Korea. When she’s not working or traveling, she is most likely on a search for the best cup of espresso.


Laura thank you for sharing Oregon with us! It looks BEAUTIFUL there! Wellspings sounds amazing right about now! I would love to have a ladies night there!

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