Midwest Memories

To some, Woodstock, Illinois is just a tiny dot on a map clumped in with Chicago. I did not spend my childhood here nor is it the place I have lived the longest - but for my family it earns the title of home, where 3 generations are preserving and creating memories.

Located about 50 miles northwest of Chicago, Woodstock is a quaint old town - circa 1852 - rich in history, culture, the arts and dedicated to preservation and sharing of its heritage. That’s definitely part of the draw for me. Not every town is interested in preserving its history, in fact, many suburbs choose the progress over preservation attitude of tear down and build new, bigger and better. It is possible to preserve history without sacrificing amenities, and Woodstock is an example.

When I was a kid I used to pass through the area on the way to my grandparents lake house in Wisconsin. Just a bored kid in the backseat of a gigantic 1971 Cadillac Coupe DeVille (think pre-electronic era) looking for one of the “signs” that meant we were getting closer. A life size cow statue as we passed through the dairy capital, a huge frog shaped building that someone sold fireworks from...the drive felt like it lasted forever, gazing out the window cornfield after cornfield, some cows, more corn, more cows. Then out in the middle of nowhere - was a little town. It always felt familiar. It didn’t change much over the years - definitely not as much as other places I had been - or as some towns surrounding it. It always retained that small town charm and vintage vibe - even as a city with a population grown to 25,000 - even today, well over a century later. The littlest big town I have known.

Several years ago after some huge life changes, I told myself I would settle in the next place that felt like home, plant some roots again and see what happens. I was always drawn to the setting and vibe of Woodstock, and knew I had found my next home the first time I saw it. It was once an old typewriter factory - Emerson Typewriters - and was 1 of 2 located in Woodstock in the early 1900’s. It was converted to a residential loft community in 2007 and is a creatives’ dream. Two story ceilings with skylights, exposed ductwork, dramatic brick and timber with an industrial flair - and cool history in every nook and cranny. A writers retreat, it was perfect.

Pleasant Valley conservation area is one of many nature areas in Woodstock, but it is my favorite. My first visit was in 2001, and I have been returning ever since. It’s my local go-to when I need to ground myself and clear my mind.

In the heart of the town (technically a city but I use it interchangeably) is the historic Woodstock Square and surrounding historic district. The square has been the backdrop for many festivals, parades, art fairs, celebrations and events for over a century. Traditions like live music at the bandstand, the annual Groundhog Day Festival or holiday Lighting of the Square. There’s a seasonal farmers market and never a shortage of things to do. The Square is lined with cool boutiques, old pubs, great food and even craft chocolate.

We have a weekly tradition of breakfast at Double Yolk Cafe. The pandemic has affected so many small businesses so we make sure to order carry out if we can’t dine in.

I was fortunate to be part of the Woodstock Childrens Summer Theater crew as a scenic artist. My daughter was part of the cast, Mary Poppins Jr. We had only been living here a couple of months when she auditioned and were pleasantly surprised when she - the “new girl” - was not just chosen, but welcomed into the theater community like they had known our family forever. Working behind the scenes at the Opera House was an extraordinary experience with an extraordinary organization. I had seen productions at the venue before - but nothing could compare to being backstage - the excitement behind the scenes and feeling the energy of those who once performed there.

Besides the history and community, why do I love living here? It oozes nostalgia. Vintage, retro, antique - it’s all here. It’s a perfectly lovely mixed bag of old and new. Quirky, random things make it feel like home. I’m more in my element than I have been in a very long time. A place I can create and be inspired by my surroundings. The community is personal and real. It’s all the little daily joys - people out walking their dogs in all weather, kids playing outside, neighbors helping one another, even watching an oddly entertaining snow blowing competition between neighbors.

Iconic reminders of decades gone by randomly dot the landscape in and around Woodstock. Interesting architecture, classic farms, stately houses with historic plaques and storied pasts. I imagined what it was like to walk the same brick streets that I walk today, and live in a prestigious Victorian mansion...dating pre 1900, holding a century of secrets within its walls. Little reminders everywhere of the people who have lived here and traditions that continue.

I glanced down and saw “Dusty 77” finger written in the concrete. 1977. I was 7. I probably drove past here with my grandparents that summer. I wondered if Dusty was graduating class of 1977, or if that was just the year Dusty carved into the wet concrete? I looked around and wondered if Dusty had lived in one of these houses and tried to imagine which one. The yellow 2 story farmhouse with the 75 year old barn still standing in back? The Sears Roebuck Catalog home next to it? Or maybe one of the little ranches that started filling in random open lots in the 1960’s...

I know I’m probably not in the majority, but I won’t be retiring to a warm climate. I love that we experience all four seasons in the Midwest - I appreciate all of them. Even the relentless, unpredictable, brutal winters - though I would definitely shorten them if I could - I would never trade our extreme four seasons for one warm one. It just wouldn’t feel like home.

And at the end of the day, whatever the season, there is joy to be found and memories to be made. I appreciate every gorgeous sunset (even those in -20 degrees) and I’m thankful to be home, here in Woodstock - in my little corner of the Midwest.