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Shoulder Season Shenanigans in Casey, Illinois

  • Writer: Charmaine Warren
    Charmaine Warren
  • 14 minutes ago
  • 3 min read

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Big Things, Small Crowds...


Let’s talk shoulder season. That sweet spot between peak travel madness and winter hibernation, when the air is crisp, the vibes are calm, and the road feels like it belongs just to you and your snacks. If you're craving a low-key adventure with a high dose of quirky charm, let me introduce you to Casey, Illinois—a tiny town with big personality (and even bigger lawn furniture).


🚗 From St. Louis to Giant Mailboxes: The Journey

Jump in your car (bonus points if your pup is riding shotgun) and head northeast from St. Louis. It’s about 137 miles of open Midwestern highway—roughly 2 hours and 15 minutes via I-70. Just enough time to blast a podcast, sip some gas station coffee, and ponder life’s biggest questions. Like: How big is too big for a rocking chair?


Spoiler: 56 feet is not too big. Not for Casey.


Charmaine smiles standing on a stool beside a giant wooden shoe with text, in a brick-walled room. Cozy ambiance, casual wear.


🎡 Welcome to Casey, IL: Home of the World’s Largest... Everything

Now, I don’t throw around the word whimsical lightly. But Casey? Casey earns it. This town has mastered the art of taking ordinary things and making them absurdly, wonderfully enormous.


You’ll find:

  • 🪑 The World's Largest Rocking Chair – Tall enough to give you vertigo just looking at it.

Charmaine in green stands beneath a giant wooden chair with black legs, arms raised. It's outdoors with landscaping, cloudy sky.

  • 📬 The World's Largest Mailbox – Yes, it’s real. Yes, you can send postcards from inside it.

Charmaine inside a giant mailbox with 2 other people; two look out, Charmaine smiles at the camera. The background features a white arched structure.


  • 🎼 The World's Largest Wind Chime – It sings when the breeze hits just right. You can try to ring it like I did... it was heavy. Also it is too large for my camera. :)

Charmaine in a black jacket observes large silver wind chimes, with a wooden fence and trees in the background. The sky is overcast.


  • ⛳️ The World's Largest Golf Tee – Just casually hanging out on the local golf course like it's no big deal.

Tall wooden tornado siren against a cloudy sky, set in a grassy park with bare trees and a distant building. Calm mood.


Plus there’s a giant pencil, giant birdcage, giant yardstick, and even a giant knitting needle. (Knitting grandma not included.)

Large yellow pencil sculpture outside brick buildings with black awnings. Overcast mood with no people.


🍂 Why Shoulder Season is the Perfect Time

Casey is cute all year round, but fall and spring? That’s when it really shines. In the shoulder seasons, the weather’s ideal for strolling without melting or freezing, the big things are still standing tall (obviously), and—this is key—the town isn’t swarmed with tourists.


Looking to turn your Casey day trip into a cozy overnight escape? Book a charming shoulder-season stay on Vrbo—think farmhouse porches, quiet country nights, and maybe even a hot tub under the stars. Fewer crowds = better rates and more dreamy stays to choose from.


Not up for the road trip? Fly into nearby airports like Indianapolis or St. Louis, rent a car, and make a mini Midwest getaway of it! Then, book your cozy shoulder-season stay on Vrbo—from rustic cabins to charming farmhouses, there’s no shortage of places to unwind after a day of giant mailbox adventures. Bonus: lower crowds mean better rates and peaceful vibes.



It feels like your own personal treasure hunt. No lines, no rush. Just you, your camera, and a whole lot of “Wait... is that a GIANT mailbox?!”



☕️ Coffee, Eats & Chill Vibes

Wandering works up an appetite, and Casey delivers:

  • Casey Coffee Company – A cozy little spot with great coffee and small-town charm. Grab a latte, kick back, and enjoy the people-watching (or oversized birdcage-watching).

  • Whitling Whimsy Café – The name alone is worth a visit, but the lunch menu? Chef’s kiss. Try the quiche. Trust me.


Large empty birdcage with a Bible verse, in an urban setting. Nearby are a road, grass, and a building. Mood is serene and contemplative.

🍷 Bonus Side Quests: Local Wineries

If you’ve got a little extra time (and maybe a designated driver), there are some sweet little wineries nearby:

  • Castle Finn Vineyard & Winery in Marshall

  • Cameo Vineyards in Greenup

Perfect for sipping local wine while pretending you’re in Tuscany, except with more cornfields and fewer tourists.


🌤 Weather Watch

It is the Midwest, so check the weather before you go. Shoulder season can surprise you with a chilly wind or an impromptu spring sprinkle—but hey, that’s part of the adventure. Pack layers, and maybe a goofy hat.


🧳 Final Thoughts: Big Fun in a Little Town

Casey, IL, is proof that you don’t need a fancy passport stamp or a five-star resort to have a memorable trip. Sometimes, all you need is a giant mailbox, a charming walkable downtown, and a little time to slow down and appreciate the weird and wonderful.

So grab your co-pilot (furry or human), hit the road, and let shoulder season be your secret travel weapon.


Been to Casey? Got a favorite “big thing”? Drop it in the comments—bonus points for photos!


TTYL! Happy Travels!

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