Discover the Magic of Small Towns :: Unveiling the Charm of Sycamore

Andrea | A Glimpse of Good
7 min readJul 3, 2023
Travel shenanigans, small towns, Sycamore Illinois, popcorn stand

Dear Small Towns,

I didn’t realize the charm awaiting us as we drove out of the O’Hare rental car lot 18+ years ago.

Honestly, the word charm wasn’t what I was thinking at all as we got further and further from shopping malls, bustling city streets, and all my Targets — HOLY CRAP! Will you even have a Target!?

The enchanting factor you have in life hasn’t always been my jam, little Small Towns. Growing up in one of your Northwest counter-parts, Walla Walla, I was excited to move up in population numbers, have a Target nearby, and get lost in a crowd.

It wasn’t you, Small Town, it was me.

{I know, Small T, another break-up cliché 🤦🏽‍♀️}

I wanted bigger, more noise, more activity, more space to explore. I was in my twenties — you understand, right? I’m sure you’ve heard it 2,000 times before.

You probably knew I’d be back, didn’t you?

Flash-forward to thirties and you led us back to one of your other Small Town friends, only in the Midwest this time.

We found ourselves driving out to see your small friend called Sycamore, Illinois.

Coming from your big city antithesis, Dallas, at the time — with Super Target’s doors welcoming me with its big red bulls-eye — I wasn’t whole-heartedly prepared for what we were driving into.

But you already knew how life throws out curveballs. We had a doozy thrown at us, and you can either give it your best swing, or dance the Macarena with a blindfold on and pretend that 90-mph ball isn’t hurtling toward your head.

I typically Macarena, but B is all action. So we hear about your Sycamore, and fly up to see it in person.

Small Town, you know there’s a mammoth difference in Dallas or Chicago living and uprooting for your calmer, quieter, no-Super-Target towns. You’re also an expert on the uniqueness of each tucked-away place you create, too.

Sometimes, I think you keep all of your charms a secret so millions of outsiders like us DON’T move into your made-for-TV towns like Stars Hollow or Mayberry.

If we all moved to your tiny towns, the quaintness inherent in a slower, sauntering town block would lose its appeal.

Visiting Sycamore

You can leave the hustle behind for good, for a sabbatical, or just visit for a weekend.

Small Town, now that you’ve got us here for over 18 years, I thought I’d share some of the gems with others that you’ve added to this Midwest Sycamore.

Where is Sycamore?

This small {almost 19,000}, captivating {ever heard of PumpkinFest?}, and open-hearted {met a lifelong friend at library story-time our first month here.} place you brought us to when there was one little grocery store called Browns Market.

I wasn’t dancing when we first drove into town — more like shaking a bit. Big city to small town again was an adjustment.

Did you intentionally design Sycamore as a tiny town tucked between the miles of corn fields and split pea fields {I think they’re pea fields — look like peas, let’s call them peas}?

You did terrific work placing Sycamore 80 minutes away from Chicago, but only 35 minutes away from St Charles and Geneva. You need to intentionally drive into it, which I’m pretty sure was your plan.

It’s a scavenger hunt for small towns. Turn off I-90 at the RV dealership, head past Goebbert’s Pumpkin and Christmas farm, take a right at the church, and follow that road until you see the white and green Sycamore water tower.

Sycamore Illinois, PumpkinFest, Small towns, Travel Shenanigans

You have arrived!

{Some people understand compass-type directions of North and South — I’m not that person — If you like landmark navigation…I’m your gal!}

It replicates the small Northwest town I grew up in of Walla Walla, Washington. But there, it’s wheat fields and A LOT of wineries — A LOT of delicious wineries!

Seriously Small Towns, how do you create the individuality in each of these places? You have a true gift!

But I digress…

Traveling To Small Town Sycamore

Your creativity inventing PumpkinFest was a stroke of genius!

{Real talk:: I can’t diminish the long hours and hard work put in by the Sycamore PumpkinFest committee + the City of Sycamore that transforms the last weekend in October into an autumn wonderland for families. Thank you for all you do to make it a weekend for families to remember.}

Alright Small T, back to my travel letter of gratitude to you for getting me out of the Big C.

I know every place on the inner-webs say that they have the best place in the fall,



Sycamore and the Wally Thurow PumpkinFest weekend should absolutely make national maps for small town life and the family time it brings.

  • Largest + most creative pumpkin display you ever did {will} see
  • Historic Home Tours {Saturday}
  • 10K Pumpkin run {Sunday morning}
  • Carnival all weekend {for Bigs & Littles}
  • Parade {Sunday afternoon}
  • Contests & performances
  • Downtown trick-or-treating from the downtown small businesses {A few stops have drink treats for the tired parents too😉}

Only you could turn the last weekend in October into a Stars Hollow {Gilmore Girls} meets The Waltons type of extravaganza. 🎃

Fun, festive weekend of all things fall, pumpkins, and good ol’ fashion Midwest Nice-ness wrapped in a steaming bag of warm cinnamon-sugar pecans.

{Do not pass go, collect the change in your couch cushions, and stop at the Courthouse corner for those warm pecans/almonds to eat while you see the biggest display of decorated googly-eyed pumpkins scattered across the courthouse lawn.}

Small T, whether you’re bringing people from far or near, for a visit or to transplant and raise their family, you’ve built another small, quaint, cherished plot of acreage here.

We need to talk about that winter weather, though. It needs some tweaking by about 30º in January and February.🥶

What Else You’ll Find in Sycamore

Small Towns, you’ve thought of everything here in downtown, and even given me my nearby Target with a skip into DeKalb. Now, if you could bring me a Trader Joe’s closer than Geneva, I’ll nominate you for Mayor! 😉

Small Towns Food Favorites

Located in downtown Sycamore

The Village ➡ Authentic Greek {Favorites:: gyro sandwich, Greek salad, Hummus, Greek coffee}

Ceseroni’s→ Breakfast & lunch {Hometown Hero breakfast sandwich + any of their coffees}

Nat’s on Maple➡ Cedar Plank Salmon every. single. time!

Ellison’s Bakery→ Take home their cinnamon bread {and maybe a day-old donut. Discounted and delicious!}

PJ’s Courthouse➡ Monday night WINGO

Cassie’s Popcorn Stand→ a delicious, steaming hot bag of popcorn to munch on as you tour downtown

Entertainment Between Meals

Sycamore Golf Course

Great Western Trail {Biking, running, walking}

Sycamore Family Fun Center {Driving range, mini-golf, pitching machines, go carts}

Sycamore Theatre {Frozen in time, with all the present-day movies + a Miss Pac-Man machine}

DeKalb County History Center {You can’t imagine all the history in one small county, Michelle and her history buffs collect some of the best exhibits to showcase it all!}

Sycamore Escape Rooms {Big city to small town, this test of wits is always a good time}

Sycamore Shopping

SIS — Shop in Style {2 adorable sisters designing a shop with too many cute wears}

Growing Roots retail + massage {Home decor, clothing, and gifts}

The GreenHouse {Plant shop with yoga pose {classes offered among the plants}

35:35 Makers Collective — {Real life etsy-esque shop featuring local creatives & their craft classes}

A Nearby Drive + a few miles

Cute place to stay… Genoa Guest House gives a vintage small town stay + HOMEMADE COOKIES 😋

Ellwood House Museum — DeKalb is the home of the Barbs {who knew Barbed wire was so profitable}

Rock Cut State Park

Skiing at Wilmot “Mountain” — More of a hill to this Northwest girl, but it was a great “mountain” to teach my kiddos to ski on when they were Littles.

With a short 12-minute drive, you can grab a coffee at Open Door Coffee in Genoa, on your way out to Russell Woods Forest Preserve for a walk, jog, or trek across the river.

Thanks, Small Town, for showing me there’s more to living than Super Targets and chain coffee shops in life!

Yours Truly,

P.S. The continued sight of visitor’s SHOCKED FACES when they grab their roll of quarters to park at a Sycamore parking meter always entertains… A DIME saves your space for two-hours and will make you feel like you took a ride in the Back to the Future DeLorean. {They take pennies and nickels too, for the few people left with loose change😂}

Andrea ~ A Glimpse of Good in a Mid Life Refresh

Travel ShenanigansSmileRaiserLifestyle Blogger50+ Style EnthusiastQueen of Quirky

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Andrea | A Glimpse of Good

Globe Gallivanter. 50+ Style Enthusiast. Book Buff. Wine Taster. Queen of Quirky | Lifestyle Blogger + Renovator of THGB