It is summertime and vacation time. Perhaps you are at the beach or in the mountains or taking a well-deserved staycation? I had the opportunity to take a really special trip I’d like to share with you. My best friend and I both turned 66 this year and in honor of that, we decided to drive the whole Route 66-in reverse. Most people depart Chicago and travel to California. We took a one-way flight to Los Angeles, rented a car, and drove east to Chicago.

The road is straight and narrow and poorly identified in some areas. Trains speed across the desert next to highways and Route 66 meanders back and forth across both the highways and the train tracks. While we did have to make an occasional U-turn and wound up in a few fields, we had little or no traffic, no trucks, and no impediments to a lovely drive. The weather was perfect (late May and early June), and we may have had 10 minutes of rain the whole 13 days. We filled our gas tank in the car whenever it was half filled. Food was abundant; we preferred diners in unique main streets in Middle America. And there was pie, a lot of pie.

My friend works for my home state of Kentucky as Main Street Director and is a great representative of the Commonwealth. Woodford Reserve, bourbon maker and official drink of the Kentucky Derby, gave us 66 boxes of bourbon balls to give away along the trip. We saw some old friends and made a lot of new friends that way.

Some of our favorite stops included Winslow Arizona, the Santa Fe Arts District (especially the Georgia O’Keeffe Museum), the Painted Desert/Petrified Forest and of course, the Grand Canyon. To get there we took a train from Williams, Arizona to the South Rim. Besides the incredible view, we saw wildlife and cowboys and were fake robbed on the train. And we can’t forget the Devil’s Rope Museum, “a Tribute to Barbed Wire.”

Meteor Crater was impressive, as were the wild donkeys of Oatman, Arizona. The National Park’s pass for seniors was very helpful and saved us money. We were able to meet our planned budget by staying in interesting motels with character. We saw giant Muffler Men, Black Wall Street in Tulsa, and the Memorial to the Oklahoma City bombing. We followed the bullets on the floor to find a speakeasy in the basement of an old bank building in Amarillo and got in by pulling the correct handle on the cigarette machine that opened the door.

We saw where the CARS movie originated in Seligman, Arizona, and dozens of Burma Shave signs. We sat in Elvis’ booth at the U-Drop Inn, and spray painted cars at the Cadillac Ranch. Every town had a museum and a mural and a few heroes to brag about. We visited the home of Garth Brooks (Yukon, Oklahoma) and I was on stage at the Coleman Theatre in Miami, Oklahoma.

In Flagstaff, I got a tattoo (temporary), and a gentleman wrote a poem for my friend and me. We saw great beauty in petroglyphs and art and music and scenery. We saw poverty in towns put out of business by the highways and the drought. We crossed through dozens of Indian reservations and met quite a diverse set of people along the route.

All in all, the two of us traveled 3028 miles across 8 states, 9 if you include Nevada for 35 miles of detour due to a rockslide. We purchased pepper spray at Walmart on the first leg of our trip. We never had to use it and always felt safe wherever we found ourselves.

2026 marks the 100th anniversary of Route 66. While my friend and I have no plans to do this trip again, we would recommend it if you are up for an adventurous road trip across the Continental Divide and have some time to meander.

Which brings me to the title of this article. As a consultant, I rarely take time off for rest and relaxation. So, this trip was unusual in that respect. I never really take off my fundraising hat.

As the Kentucky Main Street Director, my friend put us in touch with a number of her fellow Main Street Directors in other states throughout our trip. It was a pleasure to meet these individuals who work day in and day out for their communities. These folks have seen their communities thrive in good times and suffer when highways moved in and took business far away from their towns. We followed floods and saw Main Street programs offering flood relief and were lucky to be in front of major storms that caused tremendous damage to neon and other sites that already faced many challenges since COVID.

Of course, all of these communities have to raise money with limited resources, so I offered my usual free advice and resources like our books and courses (for more information see https://ourfundraisingschool.com/)

I was particularly impressed with Connie Loveland, the Tucumcari MainStreet Program Executive Director. The Tucumcari MainStreet Program is a community-driven nonprofit organization dedicated to the economic, physical, social, and cultural revitalization of downtown Tucumcari, New Mexico. Since the Program was established in 2007, $10.8 million in public and private funds have been invested in downtown Tucumcari.

In 2021, Tucumcari MainStreet Program served 49 businesses and coordinated 20 events during the year. They managed a budget of several hundred dollars’ worth of private investment and they received double that in grants from public and private sources. Sponsorship and membership are a huge part of their efforts.

Volunteers are essential to their success. Through the gift of time, 97 volunteers gave 2,493 hours of service to make the MainStreet District a great place to be!

Tucumcari has a Railroad Museum that has been re-opened for one year. It has brought life back into one of the most unique and beautiful buildings in Tucumcari, the Tucumcari Train Depot which has already welcomed some 3500 visitors.

A Great Blocks on Main Street project has been implemented in Tucumcari and invested in infrastructure updates including new streets, landscaping, and pedestrian level lighting. A Forge Business Accelerator program provides a series of training and technical assistance to prepare entrepreneurs to open businesses.

In addition to MainStreet programs, we saw many other nonprofit organizations active in their communities. Events and solicitations were visible as well as coin jars at every cash register. We appreciated the diversity of the types of organizations represented and the commitment and humanity shown by residents for their fellow citizens in each town along Route 66.

Many people travel at least a portion of Route 66 during their lifetimes. If you have the opportunity, I hope you will take a trip and of course, support the nonprofits along the way.

Happy travels!