In Portland’s Hollywood district, a neighbor-led walk inspired by Jane Jacobs helps people see a familiar street in a new way. Strong Towns PDX organizer Natalie Legras shares how she pulled together a low-key neighborhood walk that feels more like hanging out than hosting an event. Starting with a few map pins and a small group of neighbors, the walk opens up conversations about old houses turned apartments, new infill, and why some corners lost their shops. Natalie explains how donuts, farmers markets, and a welcoming volunteer culture keep people coming back, and how these modest efforts deepen care for Portland.
Hey everyone. Welcome to Bottom-Up Shorts. Today's conversation lands the day after Jane Jacobs's birthday, which is a great moment to reflect on the kind of city building that she championed and the kind that we're still working toward.
There's a line from a Strong Towns article that sticks with me: Strong Towns is Jane Jacobs in action. That idea isn't just theoretical. It's saying we need to focus at a block level on what is happening in our places, and really grow to understand from the bottom up: How do we take notice and then take action in order to make our places stronger?
I loved another article that was written by Kea Wilson. She said, "What would Jane Jacobs do in our place? She would start where she is, with what she has, and work with her neighbors." That's really the heart of it. I actually love that as a description of what we're trying to do with Bottom-Up Shorts: profile people who start with what they have, with their neighbors, and start where they are.
Today, I'm joined by Natalie Legras, a leader with Strong Towns PDX in Portland, Oregon. She's been organizing Jane's Walks in her neighborhood, including one last year, and helping others step into that role too. This is exactly the kind of local, neighbor-led work that Jacobs believed in, and I feel that's why these walks are such a great way to honor her legacy, but also help our places.
Let's get into it. Welcome, Natalie.
Thanks, Norm.
Can you describe what a Jane's Walk is, how to do one, and what it's been like to host one?
Absolutely. In my neighborhood, I live in Hollywood, in Portland. This is a really incredible district. It's a commercial district with the historic Hollywood Theatre, which is quite the destination. There's lots of housing, all different types of housing: old housing, new housing, single-family homes, towers. We've got quite a variety.
I thought it was a great opportunity to take a walk through the neighborhood with folks from around the city and folks from the neighborhood, and just see what's out there. We could see some of the new businesses that are starting up in our neighborhood and get an idea of what's going on in Hollywood.
Did you have a script? Did you have a map? What did you have as you set out?
I am probably the world's worst event planner, so I like to keep it really simple. I did a few things with the help of our Strong Towns PDX volunteers to advertise this. We sent out an email, and there was a social media post. I prepared a few things for that.
Overall, it was really just a matter of going on Google Maps and dropping a few pins. Especially last year, I had a really simple format. I like to keep it casual. I just pulled out my phone with the pins in it, and we walked around and pointed out some cool buildings.
So: "Look, that's an old brick building from 100 years ago. Look, there's some new infill, a five-over-one here." It was really fun to see and hear from everyone else in the group if they had some insight into what that building used to be or what's coming up next around the corner.
I was doing a walking tour in Providence and was talking about a structure that clearly, at some point, had a little commercial space right in the front of it and then the main house at the back. I was talking about some of the challenges for people who want to do something similar with their own homes.
As we started moving along, a woman came out of the home and said, "Hey, what are you guys up to?" I ended up having a little side conversation with her, got a bunch of extra information, and was so excited to share it with the group.
It is that period of growing an understanding of, "Hey, what's going on in my community?" Would you say there were people who were totally new to what you were doing, and what were some of their reactions?
Yes. We had a few people who had never been to our local Strong Towns PDX meetups before, so some folks maybe had been following along on social media and hadn't found the right opportunity to join in.
I will say I bribed everyone with a visit to, in my opinion, the best donuts in Portland: Doe Donuts. Shout out to them. We stopped for donuts, and I also planned it on the farmers market day so we could go at the end and grab some treats at the farmers market.
I think that made it really fun for someone who might not have been sure what this Strong Towns thing is, or what our group was, to join and just enjoy a nice walk and some donuts.
One of the benefits of going for a walk, and maybe you could reflect on this, is that you don't have to look one to one. It's a little less intimidating than showing up in a room where there's a speaker at the front, and you're cheek by jowl with other people you maybe don't know. Over time, you start to have those conversations.
Did you employ little stops along the way? Was it a continuous monologue? Did you have a loudspeaker? I'm fascinated by the technical details because, like you said, you just sort of ran with it. In the end, what did that look like?
I don't have it with me in this room, but I did bring our Strong Towns PDX little pennant flags that we've been handing out to folks, just to identify myself. I think that helped everyone know who was standing in the crowd that was gathering. It helped folks find us.
I did not have a loudspeaker. I probably could have used one because I don't have a very loud voice, but it worked out great. I just stood up on some benches as we were talking, or stopped the group three to four times throughout the walk.
I had done a little bit of research. In Portland, it's called PortlandMaps. We've got some data from the city about what buildings are and when they were built. So I had done some research, but the first time I hosted this walk, I didn't do any of that. I just pointed at stuff and said, "That looks cool. Does anyone know anything else about this?"
That was great. The conversation is organic. One person will know something about the food hall that just opened up, which I had been waiting for. Luckily, it was open the day we walked by, so we got to peek inside. It was very unstructured, and it was perfect.
A good neighborhood walk when it's hosted like this is often like a really good potluck. Everybody has something they can share, and sometimes they didn't even realize they had a granola bar in their back pocket that they can contribute. There's that realization of, "Oh, that's interesting. That reminds me of this," or, "That really helps to clarify."
One of my little party tricks that I love for walks like this is to walk up to a structure and ask, "All right, how many units are in this home?" After people start to guess, my answer is always, "It doesn't matter. These are great homes." The benefit is the shell can become home to one family, two families, three families, several unrelated adults, whatever that might look like.
Then you can actually go and count the number of mailboxes or take a look at the number of gas meters on the side and maybe get a more definitive picture. Over time, if you do it a few times, you get the group chanting back, "It doesn't matter."
The ways in which our zoning really comes to the forefront, and what we've done with our places, becomes very evident when you do it on the street. It's not just arbitrarily looking at it from a bird's-eye view on a map. It's on the street: Why isn't this still a commercial space? Why can't there be a little donut shop popping up here?
Portland has a lot of great features, and I'd love to know about your story. What brought you to Portland? Have you always been in Portland? How did you become involved in Strong Towns PDX?
Absolutely. I grew up in Oregon, but I lived in a really small town out in the middle of nowhere, about an hour away. I moved to Portland four years ago, and I actually made a choice between living here in the Hollywood district, where I live, or more in the suburbs of outer Southeast Portland.
I didn't know how much that decision would change the course of my life. I thought it would be nice to live near the MAX station here, but I really didn't know that being this close and connected to the city, to the transit, and to greenways for biking, would be such an amazing experience.
Portland has this bike festival called Pedalpalooza every summer. It's all summer, with three or four bike rides a day. I had heard about Strong Towns from YouTube and online, but then I was connected with Strong Towns PDX through some of the bike community here in Portland.
I showed up, and everyone was so extremely welcoming. I've always loved maps and architecture and buildings and seeing how things change over time, so the things they were talking about in the meetings were also very interesting to me.
The more I showed up, the more I loved the way this group inspires folks. Whether it's your first meeting, your first time showing up to something, or you've been around for a long time, this group really supports what its members are doing. If you have an idea, the answer is, "Okay, how can we help you do that?" I really appreciate the grassroots, bottom-up way of creating this community here.
Can you unpack that just a little bit more? I love that language of, if you have an idea. We sometimes have groups where it's, "Okay, you're going to have to convince the rest of us of your idea, and then maybe we'll adopt it."
What I've noticed is that some of our Local Conversation groups take the opposite approach, which is, "That's a great idea. How do we support you so you can become someone who leads that effort?" Can you share a little bit more about what that meant for you, to be empowered in that way?
Absolutely. All of us are volunteers, right? This is no one's full-time job in Portland. What that means is that if all of us want to see something happen, we have to do it ourselves. That's the community.
That might sound bad, but it's also so empowering because you don't have to ask permission to do something. You can organize a walk and say, "Hey, Strong Towns group, I'm organizing this walk. Do you want to come? Can you post it on your Instagram? Can you send it out in your email?"
Almost always, the answer is yes. What can we do? Do you need someone to work on this with you? Can we help you? Can we connect you with someone we know who would be really interested in this? It's organizing at a foundational level.
And not needing to do everything solo, or after so long that the initial energy or the spark dissipates. I think that's fantastic, and I love the way you've shared that.
Do you want to share any other tips or suggestions for somebody who wants to set up a Jane's Walk?
Definitely. First, it really helps if you show up and keep showing up. Whether that's a Strong Towns Local Conversation, your neighborhood association, or another community organization you're involved with, just become a familiar face in that group.
If you want to start a walk, you can pick a day that works for you. It doesn't have to be fancy. It doesn't have to be perfectly put together. You can put a few pins in a Google Map and walk around with some friends. It could be five people. It could be 20 people.
You can do some research if you want to, or you can just point at buildings and say, "That looks great," or, "Look at the construction they're doing on the street over there. What's going on?" Just ask those questions. Ask folks who are walking by if they know what's going on there.
I love it. It doesn't have to be totally scripted out or perfectly planned. There's no way to control the weather. There's no way to control who shows up. There's actually no way to control the serendipitous things that can occur, like you said, something being open and realizing, "Oh, we could go in and have a quick little peek around." I think that's fantastic.
By the time this comes out, Jane Jacobs Week will be in full effect. That means that by the time you listen to this as an audience member, you're going to have a full year in which you can do several practice walks and begin to develop the opportunity for that to take place. I think you'll be surprised at the real value it can have.
I can speak from my own experience too. Some of my favorite moments in Strong Towns have been when I've been able to do walking tours on the ground with people, even in areas I've never been to, and just being able to see it and perceive the shape of many hands improving our community.
Natalie, what is it that gives you hope in your community as we close?
I'm inspired by my neighbors who showed up for a walk to hang out with me for a couple hours and get a donut. Walks might not be their thing, but some folks are organizing a book club. Some folks just go out and trim the branches in front of the stop sign on their street, repaint the curb yellow when the yellow paint wears off, or, where it gets cold in the winter, shovel their neighbor's sidewalk.
It's these kinds of things. I can tell that everyone who came out to the walk last weekend really wants to see how great Portland is doing. They want our neighborhood to be better. They want our city to be better, and they're willing to jump in and take the next step. We just need the pathways, and we need to enable people to be able to do that.
When you do that, we always say, if you love your place, it'll love you back. One of the things that stands out in these types of walks is often people being like, "Oh, that's so cool," or, "Oh, I had no idea." I think that fosters a deeper sense of appreciation for what we have, as well as that resolve to take those small steps to begin to fruitfully address what's going on in our places.
Natalie, it has been a treat to have you on. Thank you so much for joining us on Bottom-Up Shorts today.
Thank you for having me.
Folks, please do go check out the Strong Towns PDX website, as well as follow them on social media. They are doing fantastic work there: Natalie and Victoria and Jeremiah and so many others who are part of the crew there.
We're so thrilled that Strong Towns has an active presence in Portland, as well as in so many other places. If you are considering setting up a Local Conversation, it is a simple but really effective thing to set up a neighborhood walk and begin to walk the community and understand it even more intimately.
When you do that, I promise it will certainly give you a deeper resolve that your community is worth working for. With that, take care, and take care of your places.
This episode was produced by Strong Towns, a nonprofit movement for building financially resilient communities. If what you heard today matters to you, deepen your connection by becoming a Strong Towns member at strongtowns.org/membership.