Autostraddle Goes Outside, in Chicago and Portland!

This article was created in partnership with REI.

Autostraddle and REI have teamed up for an exciting October event that you won’t want to miss. We’ll be experiencing the joy of the outdoors with two cute and accessible autumn hikes, one in Chicago and one in Portland! Each event will be capped at 25 people. Read on to find out how you can join up with Shelli and Vanessa in each city.

Woman sits on a rock, facing away from the camera, beholding a majestic view of a canyon

This could be you! No, this is neither Portland nor Chicago, but it is The Great Outdoors.

Walk along the lakefront with Shelli in Chicago!

Hiya my hiking hotties!

Shelli here, Culture Editor at Autostraddle dot com, Chicago Cutie, and during the fall — a dyke who loves walkabouts!

I am by no means a outdoor kinda babe, like why would I go outside — there is no TV out there and a ton of bugs — but in the fall, as I am sitting in my gorgeous apartment, windows open, curtains dancing, and a hot boozy drink in my hand, sometimes I can’t help but wonder — what’s it like out there?

And then when I snap out of making myself the main character in a Chicago romcom (complete with a lawyer love interest who I meet while dancing at a bar one night and ultimately fall in love with) I realize — I can just go out there and find out!

So, that is exactly what Autostraddle is doing in this event sponsored by REI, all with the goal to make you fall in love with the joy of the great outdoors! 25 of y’all will be able to join me outside on a perfect fall day in Chicago! We will pop on our flyest (and comfortable) outdoor fits, throw on our simple sneakers, grab a bottle of water and hit the lakefront trail on Saturday, October 29th at 11 AM! We’re gonna start at Theatre On The Lake and walk 2.5 miles to end our hike at The Peace Garden. Our starting point is easy to get to via rideshare and public transit. Don’t worry, you’ll def be able to spot me — I’ll be hopped up on cold brew and by then I’ll be a redhead.

The Chicago skyline, next to the lake, as the sun sets

Is this where you meet the LOYL (love of your life)???

It’s honestly the perfect season to meet, connect, and gather with a bunch of new queer homies. Where a bunch of us from all walks of city life can meet up, spend an hour together moving our bodies, enjoying our city, and vibing with queer babes who could become queer family. What if you meet your new bestie while walking along Chicago’s beautiful lakefront? What if you meet your new workout homie while surrounded by a group of giggling queers? Or what if you meet your date to your friend’s Halloween party and then make out and fall in lust or love? You won’t know unless you RSVP and come and kick it (and walk it out) with me!

And P.S I will be taking LOTS of pics during the event! So get ready for me to annoy you with my sexy little camera!! Also, this is Chicago — y’all know we don’t let the weather run us — so we will be doing this rain or shine!


WHAT: 2.5 beautiful miles along the lake!
WHERE: The lakefront trail, meet at Theatre On The Lake
WHEN: Saturday, October 29th, meet at 11 AM
RSVP: by filling this out, by Wednesday, October 26th!

Explore the Oaks Bottom Wildlife Refuge in Portland with Vanessa!

Babes, it’s officially Autumn, and you know what that means: Hiking season is here in the PNW! Sure, sure, summer is a great time to be out and about on the trail, but can we talk about the magic that is moss covered trees and foggy days and perfect flannel combined with a cute beanie and hiking boots? One of my favorite things about Portland is that there’s never really a time of year when you can’t go hiking, and in my opinion, things only get better outside when it gets a little bit cooler and you can beat the summer crowds.

So why am I waxing poetic about hiking? Because I want you to join me on a hike this month, obviously! Autostraddle is teaming up with REI to get y’all glowing with the joy of experiencing the outdoors this year, and I want to invite 25 of you to come experience it together at Oaks Bottom Wildlife Refuge!

A pathway in the Oaks Bottom Wildlife Refuge, adorned with trees and grass, light dappling through the flora

Now imagine this gorgeous pathway adorned with gorgeous queers!! (image from Visit Oaks Bottom Wildlife Refuge)

I chose this location with the help of our pals at REI, and the way it came about is kind of interesting, in my opinion. Here’s some super insidery behind the scenes info: When I was choosing a hike for this activity, I was adamant that it should be accessible to as many humans as possible. That means low elevation and shorter mileage, but it also meant a place that one could reasonably get to without a car. While I love the plethora of hikes around the Portland area, I do find that many of them are impossible to access with only public transport. Enter: Oaks Bottom Wildlife Refuge. You can take the MAX or the bus to get there! The walk from public transit is not insignificant — it’s anywhere from .9 miles to 1.6 miles, depending on which public transit option you decide to take — but if you feel up to adding that walking time onto our hike, it feels very cool to me that the option for public transit access is there.

I was also DELIGHTED to choose this location for our hike because I’ve personally never visited it before, despite being an avid hiker, so it will be exciting and novel for all of us — AND, to be honest, my partner and I have fallen head over heels in love with WINGSPAN this year, so the idea of going to a real life wildlife habitat, as opposed to creating one on a board in my living room, is TRULY THRILLING. Maybe you also love Wingspan? Maybe you’ve also never been to Oaks Bottom Wildlife Refuge? Maybe you’re just excited about joining a bunch of Straddlers on a fun end of October hike? I can’t wait. See you soon at the Wildlife Refuge!


WHAT: 3.5 miles hike with 220ft elevation gain
WHERE: Oaks Bottom Wildlife Refuge (We’ll gather at the Sellwood Park Trailhead parking lot and take the Oaks Bottom Loop Trail, 3.5 miles total, for as long as we want to go)
WHEN: Saturday, October 29 at 11am
WHAT TO BRING: Comfortable walking shoes, rain jacket if it’s rainy, backpack with water bottle and a snack, sunscreen (even if it’s overcast), binoculars, anything you need to be comfortable on a hike/nature walk
RSVP: by filling this out, by Wednesday, October 26th!

We can’t wait to go hiking with you!

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Vanessa is a writer, a teacher, and the community editor at Autostraddle. Very hot, very fun, very weird. Find her on twitter and instagram.

Vanessa has written 404 articles for us.


  1. Oaks Bottom is not a hike. Its a totally flat area of around 100 acres mostly water. How you would get 3 miles out of that is beyond me. Nice place but more of a walk and a very short one. Forest Park, Arboretum or Tryon Creek are the obvious choices.

  2. This is so cool. I just signed up for the Chicago walk (after googling where the Peace Park is – it’s on Buena Ave / a little south of Montrose).

    I love the lakefront and I’ve been meaning to try to find queer people to walk with, so this is perfect. Thank you Shelli for hosting!

    And Vanessa – I love Wingspan! One of my SILs got most of my extended family into it. I have two regular zoom Wingspan games with different parts of my family.

  3. This makes me so happy! I have been missing queer community to a heartbreaking degree these past few years. Hardly any events are accessible to me, as a high risk immunocompromised person with Long Covid — but outdoor hikes with minimal elevation? Now that I could safely do! This is actually the ONLY queer event I have seen posted about since 2020 that I could participate in. Bravo!

  4. Love this! Can we do a NYC one? While it’s not really a hiking destination, Central Park is beautiful, and The Ramble is pretty nature-y.

    I have never been to Chicago or Portland, but they are both on my bucket list.

    I recently learned there’s a park in Portland on a VOLCANO! Have you been to Mount Tabor Park, Vanessa (or anyone else reading this)?

    Happy Outdoors! As a lifelong New Yorker, I’ve recently gotten into nature. I’ve been to 4 national parks in Colorado with my partner, and I’m a 32 year-old Junior Park Ranger at Rocky Mountain National Park.

    I also just (as in yesterday) finished Alison Bechdel’s newest graphic memoir, “The Secret to Superhuman Strength” and I recommend it to fellow nature-interested folx.

    Shabbat Shalom! Happy Hiking!

  5. This is very exciting, especially since I live in Chicago and always appreciate a reason to go to the parks along the Lakeshore! Is this something it would make sense to bring a kid to? It seems like a potentially kid-friendly context, but I also totally understand if it’s meant to be more of an adults-only thing. (Or I guess rsvps may already be filled, in which case it’s moot. *shrug*)

  6. I would love an event in Seattle but I want to go to this sooo bad I will be driving down that Saturday. If there are any other Seattle area queers who want to go to this let me know. Maybe we can carpool. My capricorn autistic self insists we leave as soon as possible to get a good parking spot! So if you don’t mind someone bossy and weird, hit me up.

    my ig if forest.island.queer :)

    So stoked!

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