It says a lot about the character of a city, how much they are willing to put into historic preservation. “Can’t know where you’re going if you don’t know where you’ve been,” as the cliché goes. Of course, you can visit the Chicago History Museum for a macro view of the city, but what about the granular details of individual neighborhoods? There is so much to be learned in each slice of this metropolis, and if you’re lucky, your neighborhood has people passionate enough to run something like the Edgewater Historical Society.
We begin our guide today in Andersonville, in a one-room building on a corner of Ashland Avenue. The Edgewater Historical Society & Museum (EHSM, let’s say) is free to the public and open on Saturday and Sunday afternoons. Friendly, volunteer staff greets you as you walk inside. These are people who genuinely care about the neighborhood and are happy to answer questions on topics ranging from the age of heritage trees to finer details of the old Chicago Yacht Club. 
Like history, the exhibits are ever-changing. As of this writing, the most prominent features are a look at the Indigenous peoples’ history of the area, a guide to heritage trees and native plants, and review of the legendary Edgewater Beach Hotel.
Indigenous peoples have a long history around the northeast area of Chicago. Nearby streets Ridge Ave and Rogers Ave were both trails used by the Ojibwe, Odawa, and Potawatomi people to access Lake Michigan. The museum acknowledges Edgewater sits on stolen land. Artifacts from Indigenous peoples as well as settler-era Chicago abound, and one little paragraph in one little guide cannot summarize the difficult history of how “shikaakwa” became “Chicago.”
Further highlighting just how old the ground we stand on is, the Heritage Tree exhibit gives us some fascinating fodder for the rest of our walk: how old do you think that tree is? Illustrations show what species of trees live in the area, plus there is advice on how to conduct a tree survey of your own. 
Shifting over to the elegant side of 20th century Chicago, we see an exhibit on the Edgewater Beach Hotel. Formerly a massive, multi-building, multi-lawn beach resort, the only remnant left today is the Edgewater Beach Apartments at 5555 N Sheridan—aka “the pink building” you might see on posters, postcards, or outside a Red Line window passing the Bryn Mawr stop.
To picture the Chicago of any of these three exhibits is to imagine a more open space, one with fewer skyscrapers. Not to say skyscrapers are bad—skyscrapers often mean gorgeous architecture and a more vibrant community. As we continue our walk, especially getting out into the neighborhood, it’s useful to think about the ways landscapes change over the long view of history.
Heading east from Ashland, just past the shops on Clark Street, and you get into the storied subsection of Lakewood-Balmoral (you should be on Balmoral Avenue, in fact). Edgewater’s history as a playground for the rich is on display in these quirky single-family homes, but these streets are not some pretentious gated community. Folks here are friendly, green-thumbed, and if you’re here on Halloween, generous trick-or-treat hosts.
Walk directly east from the EHSM until you get to Balmoral and Glenwood, from which you can see south to 5346 N. Glenwood. It’s not on the historic homes list, but its striking blue-and-white painted exterior is a nice example of some of the aesthetics we’re in for.
To get to a historic home, you have to instead turn north: 1426 W. Rascher Avenue, a sprawling house with vintage charm that’s the crown jewel of this treasure trove of a side street.
The thing about this neighborhood is the character of each house. To walk these blocks is to wonder about the story of each decorative decision. You see paint jobs that look like they could be paying homage to The Old Country, you see gardens that look like they are tended to out of passion rather than HOA obligation.
We’d be remiss if we didn’t include at least a portion of the namesake intersection, N. Lakewood and W. Balmoral, in this guide. Pick a direction, any direction, on Lakewood? You can’t go wrong. Brick buildings, stucco buildings, ivy-covered buildings—name a flourish, it’s here. We probably should’ve said earlier that this guide is best experienced on a sunny day and you should wear comfortable shoes, because someone in your party will be saying “ooh let’s see what’s over here” at every crosswalk you come to.
Now that we’ve finished our walking tour, who’s thirsty? Let’s keep our brains working, though, and maybe go someplace that will inspire us. Someplace we can reflect on all we’ve learned about today. Let’s go to Understudy Coffee and Books.
Opened in 2023 by a couple of recent DePaul theater grads, Understudy—as its name implies—is a coffee shop for the creative set. “Aren’t they all?” You might ask. Not like Understudy. Here is a cafe attached to a bookstore, but not in perfunctory, corporatized Barnes & Noble way (the coffee’s good, for one thing). The shelves are stocked primarily with plays and books on theater production. Or if you need supplies, there’s a healthy stock of notebooks and pens, too.
That’s because Understudy was designed for creativity and collaboration as much as coffee and conversation. Owners Danny Fender and Adam Todd Crawford wanted to create a gathering space for Chicago theater people, where actors could come to find materials and technique books. It shows, too—the chairs and couches are comfortable, but this is a real lounge space. An art deco interior lends the feeling of bygone grandiosity. You practically want to break into song over your croissant.
There is a legacy of theater in Andersonville that Crawford and Fender are conscientious of fitting into. Crawford says he wanted The Understudy to look “like it had been here for 100 years and just got a fresh coat of paint,” and it seems like you could trick a newcomer into thinking that was true. Response from the community has been overwhelmingly positive, Crawford says.
Just because the space serves two needs does not mean one gets short shrift, though. “We’re not 50% bookstore, 50% coffee shop,” Crawford says. “We’re 100% bookstore and 100% coffee shop.”
You’ll find typical coffee shop fare here—bagels, pastries, and all manner of warm, caffeinated drinks. But rotating menu items, often designed by staff members, are available, too. “What we do is honor the hard work it takes to make beautiful things happen,” Crawford says, and you can taste it in the coffee. Besides coffee, there are teas and lemonades, which come in handy in the evening, when the lounge morphs into an event space for open mics and performances.
As we wrap up our adventure for the day, savoring our refreshments and reflecting on the past, present, and future of Edgewater, it’s hard not to feel grateful for community. Grateful for people who commit themselves to storytelling, grateful for whatever bonds hold a neighborhood together across time and space, and grateful (perhaps most of all) to those who provide us with coffee.