Jennifer Montgomery Shares ‘Local Lore’ With Anyone Who Wants to Tag Along

It’s Sunday evening, and a small crowd has gathered on the sidewalk of W. Jackson Avenue for a “Local Lore” walking tour led by Jennifer Montgomery. This edition, presented in partnership with Knox Heritage (where Jennifer serves on the board), promises an hour-plus of storytelling about the buildings that once lined the street and those that still stand today. With each stop, she layers in history and memory, pointing out what has been preserved and what has been lost.

“It’s super nerdy, but I have all this real estate history and information rolling around in my head,” Jennifer tells me over coffee at the Gay Street K Brew. Gotta use it or lose it, as they say.

The “Local Lore” series has been going for several years, taking place over a few weeks in the spring and then again in the fall. In 2025, each one features a different street, mostly downtown but occasionally in a surrounding historic neighborhood. You can watch Brian Hornback’s videos of previous walks here. Upcoming walks (which typically start at 6 p.m.) include: 

• Oct. 5 – Wall Avenue
• Oct. 19 – W. Depot Avenue
• Oct. 26 – W. Magnolia Avenue
• Dec. 7 – Market Square

Jennifer never knows if a handful of folks will show up, or 50. There’s a Local Lore blog and she’s working on a podcast, too. 

Less formally, Jennifer started giving history tours of downtown back in high school, 35 years ago. She is the only person I’ve ever met besides myself who skipped school to – wait for it – hang out at Lawson McGhee Library. 

Not to “smoke dope” or make out with boys. Just to read books. 

“It’s a little embarrassing,” Jennifer says, then smirks: “Truant officers don’t look at the library.”

Jennifer and I are about a decade apart—her teenage “delinquency” phase hit in the late ’80s, mine in the late ’90s—but downtown was a drag either way. There just wasn’t much to do. My version of rebellion after a library trip was sneaking off to Tomato Head to experiment with tofu while imagining my mother’s disappointment. Jennifer’s version was convincing her pseudo-derelict classmates to tag along on an impromptu history tour of downtown, complete with dates, facts and figures.

Jennifer’s evangelism of Knoxville – past, present and future – is irrepressible. She’s fashioned a 20+ year career out of it as a realtor, although this particular destiny wasn’t always a given. 

If the ’90s was a ghost town for downtown, it was a heyday for suburban retail. One of Jennifer’s college jobs (she also worked in the McClung Historical Collection) was selling men’s clothes at West Town Mall. “I caught the retail bug,” she admits. After graduating from UT, some blurry confluence of events landed her in L.A., working as the merchandising manager at a Barnes & Noble in Studio City. “I don’t remember,” Jennifer says. “I drank Starbucks for the first time and may have talked my way into a job.”

Jennifer is a natural-born girlboss. After being promoted to the flagship B&N store in Burbank, she was snatched up by Gap – the ultimate ’90s outfitter at the zenith of its retail dominance. But store management wasn’t enough; by now Jennifer was in her mid-20s and hungry for that big-dawg corporate life: “I got on my iMac, I guess it was the early internet, and I found this job listing for a Gap site locator. And I was like, Yeah, that is my dream. That is what I want to do. In my mind, I was going to live on a plane and have this carefree lifestyle.” 

Small snag: the job required a graduate degree. But Gap recognized Jennifer’s potential and part-paid her tuition to move home and study Urban and Regional Planning at UT. Meanwhile, they let her keep her insurance and employed her at the local store, a glorious dumped-out crayon box of pocket tees and pleated chinos. Fully drunk on the Gap kool-aid, Jennifer wrote her thesis on chain retail stores and why downtown Knoxville would never work. “I was trying to make it work like a regional shopping center, like it used to be,” she says. “I made some good points, but I was just a little off the mark.” 

Things were starting to happen, though. When she first moved back from L.A. in the late ’90s, Jennifer recalls watching workers liberate the Miller’s Building from the soulless black plate glass it had been encased in since an out-of-state developer decided to “modernize” it in 1972. From our table in K Brew, Jennifer and I gaze out the window across Union Avenue to the since-restored building, marveling at its intricate historic façade of brick and terra cotta boobies. 

“I had the FOMO,” Jennifer says. “So when I got stuck here, I was like, Well, I’ll just do this for a while, just be part of this downtown thing. Which I didn’t realize was gonna evolve.”

Meanwhile, Jennifer’s amazing technicolor corporate dream was fading. After 9/11, Gap’s stock plummeted from $50 to $8 a share. Fast-fashion brands like H&M, Zara and Forever 21 were circling like a shark. The company didn’t need site locators because they weren’t building new stores. 

Jennifer decided to invest in something less glossy but with a better prospectus: a real estate license and a shell of a house on Washington Avenue in Parkridge. “It was through what we called the ‘drug dealer loan’,” she explains. “Joe’s Cash Wagon would show up, like, Here for money! And you better have it, you know?” 

Also, Jennifer was in the midst of a divorce: “So, you know, no money. It was a bad, low point. And I just got to this place where I was like, OK, if I have a plan B, I’m never gonna make it. I have to believe in my bones that I am a real estate agent, and I’ll be OK.”

Jennifer went to work for Wallace Real Estate (then Coldwell Banker Wallace & Wallace Realtors). She couldn’t afford postage so she hand-walked cards around Parkridge. Her first client was a guy she met on the street. She remembers going to closings with a knot in her stomach, knowing that if it fell through, she couldn’t pay her bills. “I’m not condoning that, because I think it can interfere with the best interests of your client if you’re that nervous,” she says. “But I do think you have to commit yourself to it like there isn’t another option.” 

Jennifer kept plugging away at her own fixer-upper with the help of her uncle. “It wasn’t glamorous,” she says. “There were times I was living there when it definitely wasn’t up to code.” But people saw what she was doing, and they wanted to give it a go themselves. There was pride in DIY renovations and this collective effort to bring a historic neighborhood back to life. 

“A lot of contracts were written in my living room, where there was no furniture and no ceiling – you just saw the underside of the roof,” Jennifer recalls. “There were a lot of houses over there that were in such disrepair that they were hard to look at. My experience and the experience of a lot of my neighbors was that we were just trying to fix them up, trying to figure out how.” 

Eventually the economy came back online and Gap re-recruited Jennifer to join corporateland. But the moment had passed. She was full-on Knoxville now. “I’d already immersed myself,” she says. “I was down this path, and I couldn’t look back. I’d convinced myself that I wanted to be a part of this and that this was who I am.” 

For decades, Knox suburbs had been sprawling further out in every direction. Many historic houses in center-city neighborhoods had fallen into disrepair. But now, in the aughts, there was a surge of interest in reclaiming downtown. Not as a retail center, the possible future that Jennifer’s thesis had debunked, but as a lifestyle center. 

People started investing in downtown, with its OG residential realtor (and since-day-one Inside of Knoxville supporter) Kimberly Dixon Hamilton pioneering the path. Meanwhile in surrounding neighborhoods like Parkridge and Fourth and Gill, Jennifer’s name became ubiquitous with for-sale signs. Among my hipster friends, it was “cool” to buy a fixer-upper from Jennifer Montgomery. She wasn’t just some suburban white-bread realtor chattering clichés about “good bones.” She was in the grind herself. 

Jennifer says, “I think they wanted what I had and were like, ‘Well, Jennifer has demonstrated that she knows how to do this and she’ll get me plugged in.’ And that’s what I did. I was really just a conduit. When you’re there in the heartbeat of things, you just feel more deeply. You’re more connected to everything that’s going on in the community and the vibe of things. It’s harder to do this, even if you understand it as well as I do, if you’re outside of it.”

Years passed. Houses cycled on and off the market. About 15 years into her real estate career, Jennifer found herself feeling restless and a little burnt-out: “Like, you have these high points, and then you come off of it. You have to. So I was there, and I was looking for what else to do.” 

In the following years she and a colleague left Wallace to start their own real estate brokerage, Trotta Montgomery. She bought a hobby farm and took up carriage driving. She considered getting an MBA. She ran for City Council and became a Master Gardener. She knitted. 

Throughout it all, Jennifer and George Wallace, CEO of Wallace, stayed close. He’d been her mentor since the beginning and supported her when she decided to branch out on her own. So when she and her business partner decided to part ways a couple years ago, Jennifer called George for advice. He reminded her that the door was always open at Wallace. “So I came back,” she says.

Now she is the principal broker at Wallace’s new downtown office, which opened earlier this year at 625 S. Gay Street, AKA the rowboat building. Coincidentally it’s across the street from the building where Wallace started in 1936, in the Journal Arcade.

The space is decorated with historic signs and relics from over the years. Its centerpiece is a thrifted settee, reupholstered in red velvet. The office is tight quarters but Jennifer is glad to be downtown, in the thick of it. She enjoys walking the same streets she did as a local history nerd in high school: sometimes alone, sometimes in the company of those who appreciate the lore.

“For me, on a personal level, I’m just 100% happy here,” Jennifer says. “I’m 10 out of 10 for quality of life. This is where I belong.” 

Learn more at the Local Lore website and on Facebook.