Wednesday Walk: A Trip to Greenfield
Visiting a Massachusetts small town to rethink what makes shopping special
Welcome to Willoughby Hills!
Every Wednesday, I offer a few short ideas that I hope will inspire you to do some more reading, thinking, and exploring. Let’s take a little walk together and see where the path leads…
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A Few Podcast Updates
Before I get too deep into today’s issue, I also wanted to share a few updates on the podcast. Most of last month was spent fighting off pneumonia, affecting my voice and my energy level. As soon as that passed, it was Election Day, and it felt like a time to regroup and take some time to read, think, and process.
As such, I have decided to put new episodes of the podcast on hold through the holiday season. I will share details soon on when new episodes will be returning.
In the meantime, on Thursdays, I plan on sharing old episodes of Willoughby Hills (and its predecessor Quarantine Creatives). Some of them you may have never heard, others it may have been a few years. I’ll be carefully selecting the episodes I choose to reshare so they will hopefully be timely to our world in this present moment too.
Speaking of old episodes, I wanted to share that Matt Sexton, the Cleveland-based photographer who I interviewed in 2023 (and who also happens to be my cousin) has a new calendar of his work out for 2025 full of amazing shots all around Northeast Ohio (the January image is a beautiful shot of Squire’s Castle in the actual city of Willoughby Hills).
I ordered mine last week and if you’d like to order yours, please follow this link.
Rethinking Downtown
Last week in this column, I shared some thoughts on Black Friday and some advice from my interview with Amelia Pang about ways to make better shopping decisions.
This week, I wanted to talk about a recent trip I made to Greenfield, MA and how it got me thinking about consumption in different ways.
Greenfield was once a booming industrial town in north central Massachusetts. These days, it’s an eclectic mix of buildings that survive from the glory days, a still active downtown shopping district with a thriving arts and alternative culture vibe, and a mix of social services that attempt to aid those who didn’t weather the economic decline so well.
From 1882 until its closure in 2020, Greenfield’s Main Street was home to Wilson’s department store, one of only a handful of independent, single location department stores that survived into our modern era. I never made it to the store during its heyday, although judging from photos online, I may not have missed much.
In 2022, a plan was announced for the Wilson’s site to be redeveloped into a larger location for Green Field’s Market (a local co-op grocery store that’s outgrown its current location roughly a block away) and 65 mixed-income rental apartments. When I was there recently, no construction was visible though.
The fate of Wilson’s is honestly not that different from that of other department stores around the country, whether places like Sears, which only operates a handful of stores these days (one of which I visited last year), or mall chains like Macy’s or JCPenney, which have failed to attract the foot traffic that they used to and have seen waves of store closures and consolidation.
At one time, department stores were considered the “anchor” stores of malls because they would draw in crowds that would then visit the smaller shops too. Big stores like Sears and JCPenney would print giant “wish books” that kids like me would browse for hours, circling the toys, games, and clothes I hoped would find their way under my Christmas tree. (If you’re interested, Wishbook Web’s scans of vintage catalogs are now housed at the Internet Archive).
The decline of the department store is unsurprising. As clothing production has largely been outsourced to places like Bangladesh and China (which come with many issues that I’ve documented before), there seems to be less and less that distinguishes one brand from another.
In fact, many companies seem to no longer be focusing on unique designs at all, opting instead to sell nostalgic intellectual property. As I wrote over the summer:
“Fast fashion seems to have been distilled to its simplest form- no longer offering a stylish body covering, but instead projecting a message like ‘I’m the kind of person who enjoys the Teenage Mutant Ninja Turtles and Pizza Hut’ whether or not there’s any quality behind that message at all. And yes, that’s an actual garment you can buy.”
Against that backdrop, who can get excited about browsing the shelves of a department store? It’s all variations on the same dull theme: low quality, cheap prices, and IP disguised as design. Plus, up to 40% of the clothing produced each year is not even sold, which works out to as many as 60 billion excess garments per year! Why do we continue to buy so much new clothing when we’re literally throwing it away by the pound?
As I think about Black Friday and how we spend our money this holiday season, though, I think Greenfield can be instructive for a path forward. I spent maybe 45 minutes walking around downtown Greenfield on a rainy afternoon. Despite the rain and cold, it was a beautiful way to pass my time.
I stopped into Greenfield Records, a vintage music store specializing in vinyl but also selling cassettes and CDs that has been operating since 2009. The shop had records from all genres, including a large jazz selection and a well-organized world music collection. I picked up a vintage vinyl recording of Nat King Cole’s Christmas album, which has been playing nearly non-stop in our house ever since.
I also stopped into a consignment shop that sold used housewares, books, music, and clothing for babies, children, women, and men. I didn’t find anything that had to come home with me, but I also enjoyed browsing.
Finally, I stopped into the existing location for Green Field’s Market to buy a few food products, including a hot sauce from Hawthorne Foods in the Hudson Valley that I can’t find at other local stores.
So what made shopping on Main Street in Greenfield such a pleasurable experience when going to the mall, a department store, or a big box store can feel like such a chore?
I think a big part of it comes down to the thrill of the hunt, which is missing in modern retail. What’s the point of browsing a Macy’s, a Gap, or an H&M when it’s all slight riffs on the same, cheap, imported garbage?
Meanwhile, the stores that most caught my attention on Greenfield’s Main Street were the ones selling used items. These may have been mass produced and widely available once upon a time, but these days, they read as one-of-a-kind and unique.
By and large, used items, whether at antique stores, thrift stores, consignment shops, or speciality stores like the record shop, are also priced very well and are often of a higher quality than what’s selling at the bigger stores these days. After paying $10 for a vintage Nat King Cole record, I saw a new version of the same album selling for $30 at Barnes and Noble a few days later. Mine was pressed more than 50 years ago and I can feel the history every time I remove the record from the sleeve. And at 1/3 the cost! It’s hard to put a price tag on that.
As I look out at the future of retail, I wonder if vintage is at least part of the solution. Shopping for used items brought back the excitement of browsing in a store, which I haven’t experienced in years at most big box or department stores.
I also hope that as Black Friday approaches, we can normalize the giving of used gifts. Not everything has to be brand new to be meaningful. As I said, we have enough of everything in this world already- let’s make use of some of those things!
Some Odds and Ends from Greenfield
Greenfield not only works well because of the individual stores, but it also works well because the town is very thoughtfully designed at a human scale. Here’s a few odds and ends that I found noteworthy as I strolled around Main Street:
Bike Repair Stations
I noticed a purple post in a park and had to take a closer look. It turns out it was a bike repair station. Bikes sit on the horizontal bars and hand tools are attached to the structure with steel cables. There’s even a built in air pump. It’s a small gesture to not only make cyclists feel welcome but to also encourage biking.
Informative Sidewalk Art
All around town, there was sidewalk art that added an element of interest to walking around Main Street. But the artwork was also meant to be informative. There are twelve pieces of art around town that are part of the “Abolitionist and Underground Railroad Art Walk” which tell the story of Greenfield’s role in the abolition of slavery. Each piece of art has a QR code painted next to it that provides more information. It turns the sidewalk into a museum, and like a museum, people can engage as shallowly or as deeply as they’d like.
Nice Abandoned Stores
Like any American Main Street, there are vacancies in Greenfield. But I was struck by how nice some of the empty storefronts looked. They weren’t just covered in plywood. One storefront had a wall built maybe six feet inside of the entrance, which left the windows and door in tact, but didn’t provide a view into a giant vacant void.
Another empty storefront was selling poster space to advertise local events or activities.
As with anything, all of these little parts help create a bigger whole picture. Greenfield’s Main Street isn’t worth stopping if you’re coming from hours away (Northampton or Amherst have more going on that would appeal to tourists), but if you’re in the area, it’s a great place to spend an afternoon.
For more thoughts on what makes a good small town, take a listen to my podcast episode with Ben Napier from HGTV’s Home Town.
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Other Wednesday Walks
The Intelligence of Other Humans
If you’ve missed past issues of this newsletter, they are available to read here.
Big fan of Greenfields Market! I stop by there whenever I'm on my way to North Adams, to grab a bite to eat and browse their wholesome and interesting products, both fresh and packaged. That whole Main st shopping experience is absolutely a great time, with that oh so important essence of "the hunt" you mentioned in your post. I'm so turned off by places like Target and Walmart, selling mountains of brand new yet subpar quality items. I'd rather buy something well used, at an even lower price, that I know will last for another 50 years if taken care of properly. As a matter of fact, this whole modern Christmas gift giving ideology is a giant turn off, with that looming anxiety over most peoples heads of "Oh jeez, i gotta buy a gift for A, B, C and so on.." I wish more of us would turn to shopping centers like the one in Greenfields downtown to fulfill those gift purchasing needs, and support the people in our neighboring towns and communities, instead of feeding the monoliths of retail. Happy Holidays Heath! This is hands down, my favorite newsletter. keep up the great work!