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 championship golf to locally sourced food, fresh meats, regional wines, and authentic farm experiences.
Suggested Itinerary
Jackie recommends three to four days for this portion of the drive.
Spend time enjoying Tulsa, Oklahoma’s Route 66 museums and landmarks, then continue west while stopping frequently to experience the small towns that helped define America’s most famous highway.
Part Three: Texas and New Mexico
This stretch marks one of Route 66’s biggest transformations.
Leaving Oklahoma, travelers enter the vast openness of the Texas Panhandle before climbing into New Mexico’s dramatic high desert.
Jackie describes this portion as where “the pavement meets the sky.”
It’s also where Route 66 begins to feel almost ancient.
The landscapes become larger.
The skies become wider.
The road begins weaving through places shaped by thousands of years of Indigenous history long before Route 66 ever existed.
Along the way you’ll encounter:
- Cadillac Ranch
- The Blue Swallow Motel
- Albuquerque’s historic Central Avenue
- Santa Fe’s original Route 66 alignment
- Desert landscapes
- Endless photography opportunities
Harvest Hosts Highlights
Jackie’s favorite overnight stops include:
- The Den on 66 café
- Panarosa Valley Winery
- Junkyard on 66 Brewery
- Milburn Price Cultural Museum
Each offers its own unique experience—from award-winning wines and brewery patios to museums filled with historic artifacts and fascinating collections.
Suggested Itinerary
Allow four to five days to fully appreciate this stretch.
Jackie recommends:
- Cadillac Ranch
- Amarillo
- Santa Rosa
- Santa Fe
- Albuquerque
This slower pace allows time to enjoy the scenery while avoiding simply racing across the desert.
Part Four: Arizona to the Pacific Ocean
The final section of Route 66 delivers one unforgettable destination after another.
Arizona contains the longest uninterrupted stretch of original Route 66 pavement, making it one of the most rewarding states for classic Route 66 enthusiasts.
This is where you’ll encounter:
- Oatman and its famous wild burros
- Kingman
- Needles
- The Mojave Desert
- Pasadena
- Hollywood
- Santa Monica Pier
After more than 2,400 miles, reaching the “End of the Trail” sign at Santa Monica becomes an emotional moment for many travelers.
Jackie described it as the perfect payoff after completing the journey across America.
Harvest Hosts Highlights
Recommended overnight locations include:
- Roy’s Motel & Café
- Wildcat Winery
- Peggy Sue’s 50s Diner
- Sundowner Saloon
From vintage neon signs to hand-spun milkshakes, award-winning wines, and classic roadside diners, this stretch perfectly captures the nostalgic spirit of Route 66.
Suggested Itinerary
Jackie recommends allowing five to seven days for the final stretch.
Highlights include:
- Petrified Forest National Park
- Flagstaff
- Kingman
- Oatman
- Mojave Desert
- Peggy Sue’s 50s Diner
- San Bernardino
- Santa Monica Pier
By the time you reach the Pacific Ocean, you’ll have experienced nearly every landscape, culture, and roadside attraction that makes Route 66 legendary.
Why Fall Might Be the Best Time to Drive Route 66
One of the most practical tips Jackie shared was her recommendation to travel during September or October whenever possible.
Shoulder season offers:
- Cooler temperatures
- Fewer crowds
- Better photography light
- More comfortable desert driving
For travelers hoping to complete the entire route, autumn provides some of the best conditions from Chicago all the way to Southern California.
More Than Just Overnight Parking
Throughout the conversation, one idea kept coming up.
Harvest Hosts isn’t simply about finding a free place to park.
It’s about connecting with local businesses.
Every overnight stay becomes an opportunity to:
- Meet local owners
- Sample regional food and wine
- Learn local history
- Explore small communities
- Support family businesses
That philosophy pairs beautifully with the spirit of Route 66 itself.
Final Thoughts
Route 66 has always been about slowing down.
It’s about discovering places you never expected.
Meeting people you never planned to meet.
And collecting stories you’ll tell for years afterward.
Jackie’s outstanding four-part Route 66 guide captures exactly that spirit while making trip planning remarkably approachable for RV travelers.
Whether you’re driving all 2,400-plus miles or simply exploring one section at a time, a Route 66 Road Trip with Harvest Hosts offers an entirely new way to experience America’s most iconic highway.
The Mother Road is calling.
We’ll see you at the campground.
