Road Trip: Carefree Arizona

Carefree Arizona, once touted as “the next Palm Springs”, is just beyond the north end of Scottsdale. At one time in the not too distant past, it would have been a destination for Phoenix folks looking for a close by getaway destination. Now the expanding suburban sprawl of the greater Phoenix and Scottsdale  areas nearly put Carefree and Cave Creek within their domain.

I learned about Carefree from a midwestern buddy whose family owned a getaway home in Carefree. He went to college at Northern Arizona University, and had told me of many youthful college bound trips he made with fraternity brothers from Flagstaff down to Carefree. So, while I was familiar with the place, I had not actually been there. So, on my recent Arizona getaway, I decided I’d get on the “Old Road” and go there for myself to check it out.


Scottsdale Road ends at the ”Carefree Highway”. If “Carefree Highway” sounds familiar for some reason, you can thank the Canadian singer Gordon Lightfoot whose 1974 hit “Carefree Highway” peaked at #10 on the Billboard charts. And when you think about it, it’s a pretty great road trip tune.  Beyond the Carefree Highway,  the road becomes “Tom Darlington Drive”.  My sense of wondering “who is Tom Darlington” led me to a google search to discover that Tom Darlington was the lead developer of the Carefree development. Carefree started up in the late 1950’s with a $44, 000 investment that purchased the land that would become Carefree.


By today’s standards, some of  the “midcentury modern, meet desert” homes may seem modest.  But they were generally second homes for the “well do to”  looking for a winter destination and getaway. There was even an airstrip in the town for those residents flying in from their other homes.   What is most fun about Carefree are the whimsical street names. They sound like they were derived from a group of friends having fun sitting around after a few cocktails throwing out funny names that popped into their minds In fact…. That’s exactly what happened!  In 1958, the town’s whimsical street names come to life during a dinner party in Phoenix. Darlington’s partner in the project, K.T. Palmer, mentioned to the group that they had not yet selected names for the streets, and party guests began providing ‘colorful’ names for the new town. Which in turn, helped the new venture to generate publicity for the unique development.


Ho Hum Road, Lazy Lane, Peaceful Place, Nonchalant Avenue and Wampum Way, among others. After all, who wouldn’t want to live on Easy Street?   You can in Carefree!


Annie.... get your gun...

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