The Ultimate Route 66 RV Trip with Harvest Hosts

On this week’s episode of The RV Atlas Podcast, we continue our year-long celebration of the 100th anniversary of Route 66 with one of our favorite trip planning episodes yet. A Route 66 RV trip with Harvest Hosts sounds pretty amazing to us–so let’s dive in!
Joining us is Jackie Kutrovacz, Senior Lifecycle Marketing Manager at Harvest Hosts, who recently created an outstanding four-part Route 66 travel guide highlighting Harvest Hosts locations from Chicago to Santa Monica. More than just a collection of overnight stops, Jackie’s guide combines Route 66 history, local attractions, suggested itineraries, and memorable Harvest Hosts locations into one unforgettable road trip.
Whether you’re planning to drive the entire Mother Road or simply tackle one section at a time, this episode is filled with practical planning advice, fascinating history, and plenty of inspiration for your next RV adventure.
To listen to our interview with Jackie about a Route 66 RV trip with Harvest Hosts please click on the media player above–or subscribe to The RV Atlas podcast wherever you get your favorite shows!
Why Harvest Hosts Is Perfect for Route 66
If there was ever a road trip designed for Harvest Hosts, it’s Route 66.
Jackie explained that Harvest Hosts and Boondockers Welcome now offer approximately 1,400 overnight locations within 50 miles of Route 66, giving RVers an incredible number of options as they travel west.
The diversity of hosts is especially impressive.
Along the route you’ll find:
Wineries
Breweries
Museums
Farms
Golf courses
Drive-in movie theaters
Distilleries
Cafés
Ranches
Historic attractions
Many locations now even offer optional water and electric hookups, making overnight stays even more comfortable for RV travelers.
One of the biggest advantages of the Harvest Hosts model is that every overnight stay also supports a local business, creating a road trip that’s both memorable and meaningful.
Part One: Chicago to the Ozarks
Every Route 66 adventure has to begin in Chicago.
Jackie describes this opening stretch as classic Americana.
You’ll leave downtown Chicago and gradually trade skyscrapers for cornfields, small towns, neon signs, roadside diners, and rolling farmland before crossing the Mississippi River and entering Missouri’s Ozark region.
This is where the personality of Route 66 first begins to emerge.
Some memorable roadside attractions include:
The famous Route 66 Begin sign
The World’s Largest Catsup Bottle in Collinsville, Illinois
Cozy Dog Drive In in Springfield
Historic Lincoln sites
Charming Midwestern downtowns
Harvest Hosts Highlights
Some of Jackie’s favorite overnight stops include:
A family-owned ranch and saloon in Illinois
Skyview Drive-In Theatre
Wild Blossom Meadery
A Missouri distillery featuring craft spirits and tours
Together they showcase just how varied the Harvest Hosts network has become.
Suggested Itinerary
Jackie recommends allowing two to three days for this section.
Spend time exploring Chicago before gradually working southwest through Illinois and into Missouri, stopping in Pontiac, Springfield, and finally reaching the Ozarks without rushing.
Part Two: Kansas and Oklahoma
Although Kansas only contains about thirteen miles of Route 66, Jackie says it “packs a punch.”
Soon after, travelers enter Oklahoma—the state with the longest drivable stretch of Route 66.
This portion of the route feels distinctly different.
The scenery shifts from wheat fields to Oklahoma’s famous red earth.
The diners become a little greasier.
The neon signs become brighter.
And Route 66 begins to fully embrace its identity as The Mother Road.
Highlights include:
Pops 66 Soda Ranch
Tulsa’s Route 66 attractions
Native American history
Historic roadside architecture
Small-town Americana
Harvest Hosts Highlights
Recommended overnight stops include:
Peoria Ridge Golf Course
An award-winning winery among Oklahoma pecan groves
Route 66 Meat Market
Blended Acres family farm
These locations offer everything from champ...