To Westport, From A Flyover State

Mike Joseph graduated from Staples High School in 1971. Life has taken him far from Westport.

He still feels connected to his hometown. But naturally, his perspective has changed. He writes:

A regular reader of “06880,” I love keeping up with the ins, outs and general machinations of life back in Westport.

Like so many kids who grew up there in the ’60s, I took off for college and never looked back. Other than several close childhood friends still surviving the town’s urbanization, the ties that bind have grown decidedly tenuous.

Mike Joseph

Of course I’d love to return to Westport for all the reasons you know and love, but, um, there’s the affordability factor. It’s out of bounds for anyone calibrated to reality from out in America.

I’m now tuned for the Midwest. I live on Kansas City’s Kansas side in a very Fairfield County-like suburb, not in pot-legal but personal freedom-denied Missouri.

Our enlightened purple county is separate from the rest of the traditionally red- as-a-ruby state, with a Democratic gay American Indian congresswoman. But to my coastal friends, I’m sequestered in a flyover state.

I bought my first house here in the ‘90s — a nice little 1,500-square foot, 3 bedroom ranch – for $78,500. Really.

That was after living on an 11-acre property in a big modern farmhouse with a barn, stable, 4-car garage and a dock on a Michigan river: $120,000. Mid-America is affordable.

My current custom 5,000-square foot cedar and stone ranch was in the $200s. It’s now inflated to $450,000 – and I fight the appraisal every year.  That noted, my Southern California realtor friend says it would sell for $5 million-plus there today.

Mike Joseph’s house: $450,000 in the Midwest. In Westport …?

What was once a narrow 2-lane gravel road is not isolated anymore. I’m 8 minutes from the I-435 ring road, and 20 from downtown KC. Rush hour traffic moves at 70 with no delays.

The freeways are empty on weekends; we’re very spread out, an hour’s drive from corner to corner. My sailboat is 30 minutes away. Life’s tough.

The bad news? Sadly, developers have gotten as thick as Wisconsin mosquitos, squeezing in houses – or multi-family residential units — on every piece of former grazing land they can extort. New rooftops now stretch to the (flat) horizon.

Some NIMBY and last-one-in-close-the-door goes on, but my lovely fellow Midwesterners are often too polite to fight it. Of course I stand out, as you’d expect from any New York City media-exposed East Coaster. There’s that.

Kansas City is smack in the middle of the country.

So I begrudgingly portend that my peaceful country living is slowly eroding. Blame the mass exodus away from the corners and into the middle, instigated by ever-declining coastal weather conditions and the pandemic, the isolation migration driver.

Our red state pols of course TIF the corporations before they fund Medicaid, continuing to wave the trickle-down flag. But even that’s changing … ever so slowly.

More good? We have over 20 excellent restaurants within a 10-minute drive, half ethnic, with 5 mega-sized full-service grocery stores just as close. No, they still don’t sell alcohol; we were a dry state when I moved here, and you couldn’t use credit cards for liquor until recently, so… improvement?

In my quiet and hidden 38-home HOA (with its $45 annual fee), we have forests and nature; our backyard is a deer thruway to the big county park across the road. I can’t see any neighbors in the summer. We’re gifted with dozens of miles of creek-side bicycle trails.

Of course, there’s the obvious huge plus: cost of living. That’s the big one. We have incomes that match yours, but the COL is one-third. Cheap gas all year long, lower insurance rates, food prices that never really went up. No egg shortages either.

But property taxes are climbing fast. It’s the pressure of compression, with high population influx and behind-the-curve housing options even with the explosive build rate. 10 to 15% property increases are now the norm.

That’s still cheap compared to California, New York or Connecticut, but a shocking dose of join-the-world-reality for aging residents used to paying $2,500 for their large $300,000 homes. We’re funding infrastructure that the developers need. (I can smell the back-room stogies from here…).

It’s a good place to live with some of the best public schools in the country, mild winters, and all the perks of cultured urbanity — a world-class symphony, a new $2 billion dollar airport terminal, large convention and performance centers, art galleries, museums, vibrant jazz clubs, and a rabid sporting fan base.

From historic Union Station (foreground) to music, art and food, there’s a lot going on in Kansas City.

Let’s not forget BBQ, of course. I’ll also mention the 3 digital comm service providers hooked up to the house, 2 via direct fiber optic. I’m probably more wired than 95% of America. No pun.

With climate confusion, the tornadoes have even moved elsewhere. Dorothy has left the building, and Toto rides around in a Platinum Land Rover these days. Is that good? Just checking…

It seems our little oasis out in the prairie has been discovered. Existentially, many feel like they’re drowning in rabid development, with increasing home values and bipolar political agita. We ain’t so red anymore, with the inclusive influx of different ideologic colors and flavors.

What’s the psychological temp here? Pretty damn good. Change is happening, but it’s only relative; we’re still well differentiated from the coasts. Importantly for us aging juveniles, we’re retiring with all the benefits of a good life while keeping our fiscal heads above water. Big plus.

So, greetings from a flyover state. It’s probably not what you’ve been hearing. In fact, it’s not so bad out here at all.

I do miss salt water, though …

24 responses to “To Westport, From A Flyover State

  1. Thanks, Mike, for a wonderful (and well written!) introduction to America’s middle, as seen and lived in by one with a sharp eye, an open mind and an active sense of humor. would that more “middle countrymen” and women had a scintilla of those laudable qualities.

  2. Is this a real estate advertarticle? LoL…it’s too well written. I have to admit he’s captured my imagination….and the photo of Union Station with the balloons is stunningly enticing. I can’t imagine a better place then Westport but…he’s made me think about it.
    After my brain stopped spinning with all the beautifully written advantages, I looked at my dogs sleeping quietly in our irreplaceable 225 year old barn home and asked myself would I move? ‘There’s no place like home’. Didn’t Dorthy tell us that?

  3. Eric William Buchroeder SHS ‘70

    Looks like Dan is implementing a diabolical plan to franchise 06880. I’m not sure what the zip code is for Kansas City (and I’m too lazy to Google it). But “Where Kansas City Meets The World” has a nice ring to it. For the price of ten beach stickers you can get your own blog with a proven business model. I always knew the SHS Class of ‘71 was up to no good.

  4. Mike: nice write-up! My dad went to college in what is now considered by some to be part of flyover territory: Columbus, Ohio. He really liked it there but returned to NYC to be near family and due to job opportunities (which I suspect have been joint factors for many people over the years in where to settle, at least initially).

    With the change in the ability to work remotely, I imagine that equation will be upended in the coming years (especially with the housing affordability factor that you have pointed out).

    My wife and I recognize that we were very fortunate to have lived in NYC and then Westport at a time when both were much more affordable.

  5. Carl Addison Swanson, SHS, 66

    Kansas City is a nice city. I spent a month there one weekend. But any comparison to Westport is laughable. With the caveat, many many Westporters are living well above their means. My attorney tells me 1/2 of his clients are 2 years in arrears on their mortgage.

  6. I actually did live in Kansas City for a year for work. It IS a nice city. Very communal. Now if they could only get an NFL team?

  7. Cathy Webster, Staples HS Class of 1983

    Greetings, Mike, from your neighbor to the South! A child of Westport, I have been living in Oklahoma City since 2006 and your experiences resonate with me. My husband and I have enjoyed our historic and affordable home in the metro and our kids have attended outstanding public schools. I moved my mother here in 2017 and I told her then that most people would be poorer, fatter, less educated, and likely less politically-aligned with her Westport crowd, but they would be kinder to strangers and less entitled than she was used to. She received love and care from a far more diverse community than she had ever before experienced, a community that embraced her for the last years of her life. State politics are a horror show, but our “blue bubble” in OKC is a refuge.

  8. Eric William Buchroeder SHS ‘70

    How many Westport groupies are aware that within the greater KC community is a charming subset called: Wait for it!!!! WESTPORT!!!! Went there many times on dates when I was a lonely 33-35 year old single dude in Omaha. I had to do my “hunting” in KC only 90 minutes away.

    • Carl Addison Swanson, SHS, 66

      One thing is for sure: Kansas is the ugliest state in the union.

    • Are you and Carl competing for Don Lemon’s job?

      • Eric William Buchroeder SHS ‘70

        You talkin’ to me?

      • Carl Addison Swanson, SHS, 66

        Have you ever driven through the state? I am Don’s boss.

        • Eric “why won’t my therapist return my calls?” Buchroeder

          CAS!!! Krista!!! Stephanie!!! (not you, the other Stephanie). Have YOU checked out that cool new vape joint that just opened next to Stanton Miles on the corner of Maple Ave just a couple of blocks from the schools (and the kids) at Long Lots? How convenient for the kids!!! I think it’s called Mohegan Smoke Shop.(please ignore the cultural appropriation of the indigenous people’s community’s name it was a marketing strategist’s error) Just another good reason that Westport is becoming the most family friendly “hamlet” (oh, I’m sorry, the “hamlet of the month” is Saugatuck).One toke over the line Sweet Jesus!!!!

          • Carl Addison Swanson, SHS, 66

            Nah, just whining about Kansas. BTW, they placed the weed dispensary closer to the Greens Farms Elementary than what state mandates. When the P&Z member was informed regarding this, his response: “Oh we can do anything we want within the town limits.” My response? Ever read the Constitution. He obviously has not. State law prevails over local ordinances as Federal Law prevails over state.

  9. Well written? Thanks for the compliment! Nope, not an advertorial. That said, as a former ad agency director, a VP of communications and marketing, a magazine editorial director and a group publisher after an on-and-off career in music production, writing is often more innate than speaking. Love Westport and have great memories of growing up there as a kid. Almost don’t recognize it when I visit, tho! Our former house in Gault Park is now twice as big as originally built in ’59 – a true mega-mini-palace – and it too is unrecognizable. Bought for $30k, now appraised at $946k… but that seems too low somehow. My parents should have invested in land instead of GE and IBM stock!

  10. Bill Boyd SHS 66

    I have family in K.C. And it is lovely… But the brutal summer heat and humidity is unbearable for me! I could never live there.

  11. Such a refreshing post.

  12. As a Westporter (and longtime Easterner) transplanted to Kansas a few miles west of Mike, I can confirm every word that he says here. We moved here 10 years ago and can’t really imagine living anywhere else. Just today I was listening to a neighbor complain about rush hour traffic in KC (huh? No such thing), and all I could say was, “You really have no idea.” And yeah–cheap houses, great food and BBQ, friendly people and no tornadoes. It’s all true!

  13. Great post.

    I was on my alma mater’s website and someone posted a listing for a house in Aiken, SC. While I can’t conceive of ever moving back there, the house was a split level, 1970’s beauty, that brought back every possible memory of growing up in the ’70s. It looked to be in mint condition. 2,000 square feet, half-acre, interior planter (!). $280,000! Take my money, please!

  14. Hi Dan and Hello Mike. Thank you for your observations and wry sense of humor. I’ve served on the Board of Directors of Alphapointe ( for the past 5 years or so and have had numerous opportunities to visit Kansasa City where Alphapointe is headquartered. I understand Mike’s POV and
    did not hesitate to share his [pstong with some of my fellow Board members who live in KC. In fact I’ll be there again next month for a Board retreat. I’m looking forward to it. The song, “Kansas City” always comes to mind as we turn onto final approach over KC’s very modern airport. Now, if it was only on an ocean, I might consider relocating there!

    • Agreed. I’m a member of United Soccer Coaches’ national board of directors. They’re headquartered in Kansas City (in Union Station, in fact). I go there frequently. I always have a great time. A very cool city!

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