7 Fun Date Ideas in Portland, Oregon!

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oh portlandia. where we do even start with you for fun date ideas in portland, oregon? i am glad amanda started this series because i don’t feel like i give enough love to city that i’ve called home for more than 5 years!

since it does rain here quite a bit (we are generally in the same weather pattern as seattle), the city has had to come up with eclectic and entertaining things to do so not everyone moves away when the winter hits and (then winter stays around longer than an awkward acquaintance you see at the 80’s dance party).

that being said, be warned that the summers will trick you because they are so glorious that you believe a little rain is no big deal. this cycle has been happening for 5 years now.

Fun Dates in Portland

my husband and i love dates and we make it a priority to even schedule love days. these are the top spots for dates around portland that we’ve been on recently!

1) 80’s video dance party!

we’ve done this a few times and it’s pretty tubular, dude! most people get dressed up in their favorite pair of parachute pants and vibrantly colored shirts. i usually throw my hair up in a side pony, find bright pink lipstick and get crazy. more details here but it’s every friday night at the crystal ballroom and $6 bucks to get in while everyone dances and snaps to 80’s music videos!

2) walk the waterfront

we are pretty fortunate to live 73 steps away from the waterfront and now that we have a puppy, we get to walk along it often. one of our favorite dates is to grab our favorite coffee from barista, and do the 3 mile loop from the hawthorne bridge to the steel bridge, over & back!

things to do in portland

you can also rent bikes to ride along here and throughout the city too. we aren’t really bike people – don’t tell portland.

also, from march until christmas eve, the portland saturday (and sunday) market happens every weekend along the waterfront. you can buy awesome and zany things from the people of portlandia! and kettle corn. don’t forget that. oh and elephant ears (doughy, massive pastries covered in cinnamon and sugar).

3) powell’s bookstore date

believe it or not, powell’s stretches an entire city block and they have 4 other locations too! it’s a book lover’s oasis. we happen to love browsing books together and then usually end up at a restaurant nearby. each and every time we go, i go straight to the business/public speaking section and make my husband take a picture with new his book on the shelves there. extremely proud wife right here!

make sure you go to the “rare book room” while you’re there too!

7 date ideas in portland oregon

4) distillery tour

fine, portland is better known for having the largest amount of mico-breweries (31 to be exact)  than any other city in the country but beer sucks we prefer liquor or wine. there is now something called ‘distillery row‘ which features 7 independent distilleries crafting vodka, gin, rum and whiskey!

i’m going to suggest you go to le bistro montage and get some crazy mac ‘n cheese (with or without alligator, your call) to soak up some of that booze afterwards.

5) happy hour galore!

portland is packed with excellent restaurants and bars that serve up happy hour right! if we are feeling fancy, then we like to go to departure’s rooftop bar and plan to take over see the world.

in the winter, it gets dark at like 4:15pm here so you can still catch the night lights during happy hour (4-6pm and then 10pm-close tuesday through thursday).

downtown portland at night

portland city grill has an excellent happy hour too (one of the best burgers) with an awesome view of the city (when it’s not gloomy out).

or if you go there for lunch, any glass of wine is only $5…including this champagne that is usually $25 for a glass. i don’t even like champagne that much but i had to get it because i know a good deal when i see it. dates can happen during lunch too, folks! that’s what’s called “afternoon delight.”


there are a ton of quirky bars all over portland and you really can’t go wrong. one that sticks out is the totally vegan bar (which in no way means healthy) the bye and bye. happy hour 4-7pm every day!

6) private karaoke  party

this may be more of a group date thing (or not because serenading each other could be sexy fun or just hilarious, in our case) but you can affordably rent out your own private karaoke room at the voicebox in both NE and SE portland!  i’m talking like $5-$8 an hour (per person) for less than 10 people or there are group rates!

i’ve dropped britney spears in there, tom petty and some trey songz just to be well-rounded. they also serve food and booze if you need a little extra motivation. duets are strongly encouraged.

7) get your sweet tooth on!

for some reason, many of our dates involve going to get dessert and portland is the perfect place to indulge.

of course if you’re visiting, you’ll want to check out voodoo donuts because everyone will ask if you did. plus you can buy underwear there that says ‘the magic is in the hole,’ and that makes me laugh.

our favorite places include salt+straw very fancy ice cream (their flavors will blow your mind in a good way). please note the raindrops on my glasses because it’s portland.

date night portland salt and straw chelsea and ryan avery

our other favorite place to go on a special date night is papa haydn! it’s spendy but worth it. i’ve never eaten a full meal there but have been countless time for desserts. it’s a popular place so if you don’t want to wait to be seated to eat your cake, you can get it to go and sit elsewhere (or in your car because it’s probably raining).

i’ll just leave this right here:

compliments of papa haydn

compliments of papa haydn

this list has inspired me to put together a longer list of fun things to do when you come visit portland so be on the look out coming soon!

join up to feature your favorite date spots in your city if you so feel like it!

Fun Dates in PortlandNotes from a Newlywedquestions:
1) what is a funky, fun date activity to do in your town?
2) how do you feel about publicly singing and dancing?
3) last date you went on?


  1. Cassie

    January 20, 2015 at 9:20 am

    I am so pinning this. I grew up in California and then lived in Arizona but still have never made it to Portland. I know I would fall in love!

    • chelsea

      January 20, 2015 at 10:47 am

      you HAVE to come play in portland, cassie! it’s spectacular and you will totally fall in love. come visit in june-october and you should be good 🙂

  2. LIndsay @ The Wife in Training

    January 20, 2015 at 10:50 am

    I want to come to Portland and do every single one of these things.

    • chelsea

      January 20, 2015 at 10:55 am

      do it!!! i couldn’t even begin to talk about brunch in this fair land but it will blow your pants off…in a good way. COME PLAY.
      chelsea recently posted…7 Fun Date Ideas in Portland, Oregon!

  3. Elizabeth T

    January 20, 2015 at 12:36 pm

    So I’m pretty sure I’m going to have to somehow convince my husband we need to move to Portland. Like…soon.
    Elizabeth T recently posted…Can You Take a Roadtrip in Hawaii??? {January Date Night}

  4. Amanda

    January 20, 2015 at 12:51 pm

    Umm yeah, you successfully convinced me that Portland is awesome. Any town that regularly hosts ’80s dance parties is coo by me.
    Of course, I’d also go for a date that involved stalking the Grimm set, haha. #obsessed
    Amanda recently posted…Date Nights in Fargo: Tell Me About Your Town

    • chelsea

      January 20, 2015 at 1:02 pm

      it’s pretty great out here, amanda! plus everyone basically sort of just looks like they are at an 80s hipster party all day every day. that would be a great date to talk the grimm set! i’ve seen them around!!

  5. Ashley Servis

    January 20, 2015 at 8:26 pm

    I live in stayton. An hour and half away and I cannot wait to explore Portland this summer with my husband. We have lived here for four years now and I really need to explore! Cannot wait to read more.
    Ashley Servis recently posted…Be Spontaneous In The Kitchen

    • chelsea

      January 21, 2015 at 8:40 am

      wooohoo! so glad you’re coming to play in portland this summer, ashley! i’m going to put together a larger list so hopefully you can fill your days here with lots of fun things!
      chelsea recently posted…7 Fun Date Ideas in Portland, Oregon!

  6. jennifermckennasays

    January 20, 2015 at 9:03 pm

    1. Austin, Texas- One of the early dates we went on was “Lucy in Disguise” trying on costumes didn’t cost a dime and I also found out his favourite holiday is Halloween
    2. Publicly singing and dancing- Its simply the way the Haston Family does things.
    3.On my birthday, Jeremy and I went to the movies for “Into the Woods” and we pretended it was a “first date”

    • chelsea

      January 21, 2015 at 8:42 am

      ohh that’s a fun date, jennifer! i’ve only spent a little bit of time in austin but apparently portland stole your ‘keep portland/austin weird’ so i know it’s a fun quirky place too! love that you pretended you were on a ‘first date’ for seeing that movie-how cute!

  7. Courtney! @ Redefining Athlete

    January 21, 2015 at 1:16 pm

    yay! I’m glad you posted this. We’re visiting this weekend for my husband’s birthday. I already had Voodoo Donut and Powell’s on our list, but I’m so adding that mac and cheese 🙂
    Courtney! @ Redefining Athlete recently posted…Disney Bound! & A Runner’s Guide to Kansas City!

    • chelsea

      January 21, 2015 at 1:57 pm

      hoooray courtney! i’m so glad you are coming here this weekend!!! it’s a good weekend to have a birthday (mine is this weekend too and my mom is coming to visit)! it’s even supposed to be sunny! you are going to have a blast at le bistro montage! make sure you save a little so you can get their famous ‘to-go’ works of art 🙂
      chelsea recently posted…Married Life Chats Vol. I

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