Well, travelers… Whimsy here!
Dust off your road-trip playlist, find those sunglasses you swore were in the glovebox, and point that hood ornament toward Oklahoma, because Route 66 is celebrating its 100th birthday in 2026.
And she is NOT celebrating quietly.
We’re talking hot-air balloons, classic cars, live music, historic theaters, a famous round barn, a Veterans Day parade and enough Mother Road nostalgia to make you seriously consider buying fuzzy dice.
Best of all? A whole bunch of it is happening within road-tripping distance of Whimsy Waypoint.
So grab your calendar. Here are a few adventures I’ve circled in red…
🎈 Route 66 Centennial Balloon Festival
September 11–13 | Kellyville, Oklahoma
Want to see Route 66 from a slightly higher elevation?
Try a balloon.
The Centennial Route 66 Balloon Festival takes over the Creek County Fairgrounds for three days with more than a dozen hot-air balloons, tethered balloon rides, a kite show, helicopter rides, live music, food trucks, vendors and family entertainment.
Admission is listed at $20 for adults and $10 for kids, with free parking.
Whimsy question: Sunset balloon glow or sunrise balloon launch?
I vote both. Sleep is overrated on road trips.
🎬 Route 66 Comes to Vinita
September 20 | Center Theater on 66
Here’s one practically in our backyard.
The Oklahoma Historical Society is bringing its new documentary, “Crossroads of America: Oklahoma’s Route 66,” to Vinita’s Center Theater on 66 on September 20.
The film explores why Oklahoma sits right at the heart of the Mother Road and tells stories of the people keeping Route 66 alive as it rolls into its next century.
Stay at Whimsy Waypoint, spend the day exploring, catch the film and then come back to the woods for a fire and a soak.
Now THAT is my kind of history lesson. 🔥
🚘 Route 66 Cruisers Car & Motorcycle Show
September 25–26 | Claremore Lake
Chrome lovers, this one’s for you.
The 18th Annual Route 66 Cruisers Car & Motorcycle Show rolls into Claremore Lake September 25–26.
Expect beautiful machines, plenty of Route 66 personality and an excellent excuse to debate which classic car you’d choose if someone handed you the keys.
Mine?
Classified information.
But it definitely has enough room for luggage. 😎
🚗 Centennial Car Show + Cars Under the Stars
September 26 | Tee Pee Drive-In, Sapulpa
Classic cars at an old-school drive-in during Route 66’s 100th birthday year?
Someone understood the assignment.
The Oklahoma Route 66 Association is hosting a Centennial Car Show followed by a screening of Disney-Pixar’s Cars at the historic Tee Pee Drive-In.
If you’ve got little travelers along for the ride, this one practically plans the family road trip for you.
🎻 Round Barn Round-Up
October 17 | Arcadia, Oklahoma
Next stop: one of Oklahoma’s great Route 66 icons.
The Round Barn Round-Up brings music and arts to Arcadia’s historic Round Barn, including a fiddle contest inspired by Otto Funk, who famously traveled Route 66 country in the 1920s playing his fiddle along the way.
Historic barn. Live music. Oklahoma autumn. Route 66.
That’s four good reasons to fill the gas tank.
🇺🇸 The Big One: Route 66 Birthday Bash + Veterans Day Parade
November 11 | Tulsa
Route 66’s official birthday is November 11, and Tulsa plans to celebrate 100 years of America’s Mother Road alongside Veterans Day.
The Route 66 Tulsa Birthday Bash + Veterans Day Parade is planned as a citywide celebration featuring the parade, live music and performances around downtown Tulsa, culminating with a concert at legendary Cain’s Ballroom.
For us here at Whimsy Waypoint, this one feels especially fitting. Our first cabin, Mission Base, was created with a playful military-inspired theme and plenty of appreciation for those who’ve served.
A century of Route 66. Veterans Day. Oklahoma history.
That’s a pretty special day on the Mother Road. 🇺🇸
🗺️ Make Whimsy Waypoint Your Route 66 Basecamp
Here’s my proposition:
Don’t just drive Route 66.
Stay awhile.
Explore Vinita. Wander the Mother Road. Catch an event. Visit Grand Lake. Hunt down roadside oddities. Take too many pictures. Then leave the pavement behind and retreat to the woods at Whimsy Waypoint.
And now you have two wonderfully different places to call basecamp.
Set up headquarters at Mission Base, our military-inspired cabin, where you can finish the day around your private firepit, slip into the outdoor soaking tub, listen to the trees and start plotting tomorrow’s adventure.
Or mosey over to our newly opened Stumble Rock Inn, our Western-themed cabin where the Old West gets a healthy dose of Whimsy. It’s another one-of-a-kind place to kick off your boots, settle in and make your Route 66 road trip a little more memorable. 🤠
Mission Base and Stumble Rock Inn are both officially open and welcoming travelers.
Because Route 66 was never really about getting somewhere as quickly as possible.
It was about everything you discovered along the way.
And in its 100th year, there may never be a better excuse to come discover it for yourself.
So tell me, traveler: which one’s going on your calendar? 🎈🚘🎻🇺🇸
I’ll save you a spot by the fire.
Until the next adventure,
Whimsy 🧭
Your guide to getting wonderfully sidetracked at Whimsy Waypoint.