– Cleveland, Ohio

Most people only know Overland as a trim level for the Jeep Grand Cherokee. It’s actually deeply rooted in Jeep’s history; the original name for the brand was Willys-Overland Motor Company, so named after John North Willys bought the Overland Automotive Division of Standard Wheel Company in 1908. In fact, Overland was part of the company name all the way up until the 1950s when “Jeep” replaced it.

History lesson over. All you need to know now is that Jeep makes good money off the Grand Cherokee Overland because it’s an uber-expensive, top-tier trim level. So it makes total sense that Jeep is trying this out on the less-expensive Cherokee compact crossover. Here we have it: the most gussied-up and expensive Cherokee you can buy.

2014 Jeep Cherokee Trailhawk



  • The Cherokee Overland is remarkably civil and refined to drive. The 3.2-liter V6 engine never has to work very hard to move this compact crossover around and therefore sounds quiet and distant in most situations, and the ride is as plush as the sheepskin lining of an actual Overland coat (no relation). While this won’t appeal to the rough-and-tumble Wrangler crowd, it may help Jeep attract buyers that prefer cosseting to rock crawling.
  • I may be the first automotive journalist to applaud the Jeep Cherokee’s nine-speed automatic transmission. It’s been used in a number of Fiat Chrysler Automobiles (FCA) vehicles and has been panned in the past for its tendency to hunt for gears among the many from which it has to choose. It was even recalled this past August. However, after a number of updates to address complaints, the latest version in this 2017 model year Cherokee worked admirably; it was usually in the right gear for what I needed at the time and otherwise didn’t draw attention to itself. The only situation that saw it hunting around was while the adaptive cruise control was activated and the car was constantly accelerating and decelerating.
  • As fully loaded compact crossovers go, there aren’t many more fully loaded than this one (unless you step up to expensive luxury models). Pick a premium feature and this Overland model probably offers it: automatic crash avoidance, parallel and perpendicular parking assist, a dual-pane panoramic sunroof, power rear liftgate, bi-xenon headlights, adaptive cruise control – the list goes on. Sure, you’re paying for it all, but many mainstream crossovers don’t even offer some of these features yet.


  • The Cherokee’s styling looks weird enough as-is. Seeing it with body panels that are all the same color does not help matters. The Cherokee has always looked best in the beefed-up duds of the Trailhawk model that sport off-color cladding around the face and bottom of the vehicle, as well as a cool contrasting patch on the hood. Seeing it this way, dipped entirely in Deep Cherry Red Crystal Pearl Coat, makes it look like a one-piece Matchbox car that was spray-painted on an assembly line.
  • Nearly $44,000 is a ridiculous price to pay for a compact crossover not named Mercedes or Audi. That's $20,000 more than the Cherokee’s base price of $23,595, which means Jeep believes the Overland model is worth almost as much as two base Cherokees. Or consider this: a similarly optioned Ford Escape Titanium costs about $6,500 less than the Cherokee Overland. You have to really want a Jeep and nothing else to be willing to cover that spread.
  • The Cherokee Overland’s handling is surprisingly spongy. I’m used to Jeeps not driving like cars in the corners, but I expect them to feel more like a stiffly sprung truck than a wallowing station wagon. While the soft suspension tuning earned a Pro mention from me for offering a comfortable ride, it rolls over in the corners like it’s not even trying to keep things level. Look elsewhere if you want your crossover to approximate the driving dynamics of a car; this feels more like a minivan.



Photos: John Neff / Motor1.com & Autoblog

Gallery: 2017 Jeep Cherokee Overland: Review

Photo by: John Neff


Engine 3.2-Liter V6
Output 271 Horsepower / 239 Pound-Feet
Transmission 9-Speed Automatic
Efficiency 18 City / 26 Highway / 21 Combined
Drive Type All-Wheel Drive
Weight 4,108 Pounds
Seating Capacity 5
Cargo Volume 24.6 / 54.9 Cubic Feet
Base Price $38,595
As-Tested Price $43,730
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