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Perfect solo date (but also feel free to have a friend tag along), in Portland. Transit friendly , walkable and bike friendly. Introducing beautiful views, thrifting, local food recommendations for lunch and dinner. 

Solo Date ideas in Portland Oregon! 

Explore South Waterfront Greenway in Downtown Portland, ideal for walking or running, while enjoying lush views. Pack essentials and wear comfortable shoes for the long, scenic route.

Scenic Walk

✅ Before you go
• make sure to pack your sunscreen
• metered parking if you bring a car
• if you’re bringing a furry friend make sure to bring poop bags!
• bring refreshments to stay hydrated and snacks, this greenway goes for miles down south
• bring comfortable walking/running shoes 

💪 Pro tips
• go during the day to enjoy the sun and views!
• there is construction at some point (and for a short time) but it does not obstruct the the walk way.

South Waterfront Greenway 

Visit Eem for an exceptional Thai BBQ experience. Enjoy appetizers and creative cocktails in a vibrant environment. Don't miss the chicken!

Thai Dining

✅ Before you go
• bring an empty stomach!


💪 Pro tips
• order appetizers
• a drink!
• and enjoy the vibrant mood!
• love the chicken here!


Eem 

Visit Alchemy Plants & Thrift near Eem for a delightful thrifting experience with a chance to find unique treasures like Astrological Keychains or a dumpling candle.

Thrifting

✅ Before you go
• 

💪 Pro tips
• near Eem! 


Alchemy thrift 

Explore the Alberta Arts District on 21st in Portland for a diverse array of thrift stores and cute local shops.

Thrift Shopping

✅ Before you go
• 

💪 Pro tips
• a whole street filled with thrift and cute stores!!

Alberta Arts District on 21st

Enjoy exquisite pasta and wine pairings at Gumba in Portland's Alberta Arts District. Remember to make a reservation beforehand for the best experience.

Fine Dining

✅ Before you go
• Make a reservation!!

💪 Pro tips
• order with wine 🤍

Gumba

I'm taking you along for a little solo adventure in Portland, Oregon.

I started off by enjoying these lush green ways. People.

I swear Portland has some serious nature game going on.

It was the perfect way to start my day just relaxing,

enjoying the views and the sunrise after that stroll, I decided to get some food.

is a Thai restaurant just located north of Portland, Oregon.

vibrant to tropical greenery and it just felt so fresh to

be inside because look at all of these plants so beautiful.

I wasn't too hungry this morning. I did opt to order some fried chicken and a

vegetable dish. I would say my experience here was a little lackluster,

but maybe because I didn't order like the main courses that were recommended,

but I thought their drinks were named very cleverly like they had arranged marriage

After getting some food, I really wanted to go shopping.

So I stumbled upon this place called the alchemy.

I was so excited because it's been a while since I've been thrifting.

So I was really looking forward to what I'd find today.

We're talking like Disco Planners, Astrological Keychains and yes,

I took a little bit more of a walk down and

I stumbled upon this pop up shop for local artists.

cute figurines and I couldn't help but support a local Filipino vendor.

So I ended up buying this car that said Mahal

which means I love you very much my love in the

And I gifted that card when my fiance finally arrived to Oregon.

After stumbling upon that great find, I decided to hop on some bike,

town bikes and cruise my way to Alberta Arts District.

I had first heard about this place on tiktok

and what caught my eye was the vintage cowgirl boots I saw in the video.

So I wanted to see them for myself. And I was also on the look for a leather belt.

I also found this corset for a really great price,

but let's just say my bus didn't quite fill it out.

Gumba. This place is a definite must people make a reservation?

Don't even get me started on the wine pairings.

They're absolute perfection another day and another adventure in the books.

So yeah, if you ever thought of doing a solo date slash adventure.

I commend you to do it. It's so much fun. Live your life to the fullest.

Stay curious and above all. See you next time.

Enjoy some happy hour apps in the Montavilla area and then take a stroll through one of Portland’s largest park to catch the sunset!

Weekday Happy Hour🍹+ Golden Hour 🌅 in SE 

At Thatchers in Montavilla, Portland, enjoy happy hour specialties like poppers and cauliflower bites as well as Taco Thursdays deals.

Happy Hour Dining

✅ Before you go
• They offer deals for Taco Thursdays
• They only offer ground beef tacos for Taco Thursdays 
• They are known for their Philly cheesesteaks 

💪 Pro tip
• Happy Hour deals on the menu have an “HH” in front of the menu item. 
• We ordered the poppers, cauli bites, soft tacos, and hard shell tacos 
• They offer weekly tequila specials 

Enjoy apps at Thatchers 

Enjoy a picturesque sunset at Mt. Tabor Park in Portland, complete with trails, grassy picnic areas, and limited parking.

Sunset Watching

✅ Before you go
• Street Parking and Parking lot access are available but limited. 
• There are 3 trails that go through Mount Tabor https://www.taborfriends.org/maps
• There are mosquitoes! If you’re prone to getting bug bites, bring bug spray 
• Plenty of grassy areas, bring a picnic blanket to hang out on

💪 Pro tips
• To park near the summit, drive down Mt. Tabor 
• To park near the reservoir, drive down SE Salmon Way or SE Reservoir Loop Dr

Catch the Sunset at Mt. Tabor Park

Here's a weekday itinerary to enjoy some time outside.

We'll get some cheap eats at a chill dive bar and then

catch the sunset at one of the largest parks in Southeast Portland.

So we're heading to the Montavilla area to check out Thatcher's for happy hour.

but most of their items are around $6 so I got the poppers and the cauliflower bites.

Because they have deals for Taco Thursdays.

We then headed over to Mount Tabor Park to catch the sunset.

The park is built on an extinct volcano and has a few trails you can walk on.

We initially headed to the summit where you're encapsulated by the

trees and it feels like you're away from the city.

Another favorite spot of the park is the reservoir.

I love looking into the reflection of the water and

you can see the city skyline in the distance.

So grab a friend and make the most of a weekday evening with good bites, 

and a little adventure in Southeast Portland.

Sip and savor some delicious beer and food here! It’s a great spot to hang out and unwind. They’ve also got fun events going on throughout the year. Cheers! 🍻 

Cheers to Level Beer 🍻 

At Level Beer in Argay, Portland, enjoy a wide selection of beers and expert advice from knowledgeable bartenders. Perfect for trying new brews!

Beer Tasting

💪 Pro tips
• The bartenders know their beer so don’t be afraid to ask lots of questions and try new things! 

Grab a beer

At Level Beer in Portland, you can indulge in a variety of food from different trucks, including a must-try dessert truck. Come hungry and enjoy!

Food Trucks Dining

✅ Before you go
• Come hungry! There are food trucks with lots of options! 

💪 Pro tips
• Don’t miss out on the dessert truck! 

Grab some food

They've got great flavors and have something on the menu for everyone.

and my husband likes more hoppy and bitter flavors,

and we both found something we really enjoyed.

Then we raced over to the food carts and grabbed a ton of different options.

We also loved the ambience created in the seating area.

of different events going on throughout the month.

It’s wildflower season! And you gotta check out the Mosier Plateau trail. This 3 mile hike is located just past Hood River, about an hour away from Portland.

Hike with Wildflowers along Mosier Plateau 🌼

Explore Mosier Plateau Trail for a scenic 3-mile hike featuring wildflowers, a waterfall, and stunning views over the Columbia River. Ideal for spring outings when wildflowers bloom.

Hiking

✅ Before you go
• Bring something to cover your ears as the top of the trail can be very windy.
• During the busy seasons, parking can be tough. There is a lot close to the trailhead, but a lot of people also park along the side of the road. Just be sure you aren’t blocking any roadways when parking.

💪 Pro tips
• Hit up Hood River after for some good food!

Mosier Plateau Trail

It's wildflower season and you've got to check out the Mosier Plateau Trail.

This 3 mile hike is located just past Hood River,

you'll find a picturesque waterfall waiting for you.

It's a great start and a motivator to the top!

but maybe not as much as you'll see in this video.

I did love watching the grass and flowers blow in the wind

I've been on a few wildflower hikes in this area,

but the view at the top of this trail is the best hands down.

The overlook towards the Columbia River is definitely worth the climb,

there's a small path to keep going for another 0.5 mile or so,

or you can call it the halfway point and start your trek back.

If you're looking to see the spring wildflowers

with an added sprinkle of waterfalls and gorgeous views,

as they are in full bloom through May and June.

Take some time to enjoy the spring season in Oregon!

Cafe and restaurant daytime DJ sets are popping up around Portland, so check out this group who organizes these events! 


Here's your plan for enjoying a vibrant brunch with DJ sets and flavorful Vietnamese coffee

Spins, sips, and brunch pop-up ☕️🎶

Enjoy a vibrant DJ brunch with strong Vietnamese coffee and Asian fusion dishes at Prime Tap House during the annual event hosted by How Sweet.

Brunch DJ Event

✅ Before you go
• check out How Sweet Instagram page for future pop-up events https://www.instagram.com/howsweet.pdx?igsh=MWpqZzdpNDJhZGZneg==
• Saigonesso sells their coffee drinks at Ding Ting https://www.instagram.com/saigonesso?igsh=ZHl3c2k3eTVibjdl
• Prime Tap House only serves brunch once a year, on regular days they are a brewery & wings restaurant https://www.instagram.com/primetaphouse?igsh=NnF5aW5sdzBnd3Ex

💪 Pro tip
• If How Sweet is hosting a cafe or brunch event, it will be PACKED, so get there at opening or expect a wait

Turn up & Sunny Side Up with How Sweet at Prime Tap House

Prime Tap House hosted their annual brunch event,

and they partnered with How Sweet and Saigonesso

This was the line for Saigonesso within 30 minutes of opening,

but it was worth the wait because their coffee was so strong and flavorful.

they were serving Asian fusion dishes and my friends and I got one of everything.

My favorite dish was the mango sticky rice French toast,

Nothing brings the community together like good food and good music,

so be on the lookout for more events that will be hosted by How Sweet in the future.