Although the practice of embarking on a leisurely Sunday drive or youthful road trip has existed for generations, a website now allows modern driving enthusiasts to take such pursuits to extremes. Travelmapping.net provides users with the opportunity to document their travels on the following types of highways: interstates, U.S. numbered systems, national park loops, historic decommissioned byways, numbered state roads, named freeways, major parkways, and even select international routes. Not only does Travelmapping provide beginning points, end points, and intersections for all of the above categories, the service also compiles a plethora of statistics, progress maps, and rankings for all registered members. This information is available completely free of charge, as the site was developed by, is maintained by, and continues to be constantly expanded by volunteer programmers who refer to the hobby of purposely driving roads to completion as highway clinching.

You might be wondering how I discovered such an affinity group. My passion for mapping actually predates mainstream Internet access by a couple decades. Growing up on a farm outside of Ridgely, I was a regular shotgun companion as my father drove to pick up tractor parts or livestock throughout the Mid-Atlantic and Canada. Whether it was because he legitimately did not want to take his eyes off the road or was already familiar with the directions but did not want to hear constant flow of consciousness chatter from an inquisitive young mind is of little consequence — he handed over the Rand McNally atlas and told me to plot the best course to our intended destination. So began my love affair with maps.

Soon after I was old enough to acquire a driver’s license, I started planning road trips of my own. After one excursion that took me from Maryland to Tennessee to Florida and back, I began wondering if there was a way to document, at the very least, the interstate routes I had traveled in my lifetime. The Internet was still fairly new and clunky then to the extent that even basic black and white outline maps of states, let alone highways, were hard to come by. Alternately, I considered using a highlighter to mark my roads state by state on a road atlas but could not do that either: the small text and compact pages proved unsatisfactory for that purpose, not to mention the fact that perennial highway construction would render this option obsolete on an almost yearly basis. About five years later, however, I noticed that Wikipedia was rapidly growing and becoming ever more locally specific. Users were adding national and state highways within the respective borders to each county page. Curious as to where the editors were confirming this information, I googled until I landed on several web sites dedicated to the study of even the most inconsequential of roads. One such resource made reference to an early version of Travelmapping, and as a result, I have been documenting my travels and planning new excursions to log ever since.

My wife thinks I am crazy. She not so playfully accuses me of going out of the way to “get new roads” on trips even when I am not attempting to do so. She encourages me to pursue the hobby by myself or with our dogs. It might be boring for her or most others to just ride, but not me. Not only do I enjoy the thrill of “clinching” as well as the leisurely sightseeing of nothing in particular, I am also convinced that with each outing I will find something on one of these obscure roads that I never knew was there. Even capturing a bucolic nature scene with my camera or a light-hearted Snapchat moment to share would be sufficient. On more than one occasion, on my own or with my family, it should be noted, my study of maps has proven invaluable when choosing alternate routes to avoid accidents, road closures, or other unforeseen delays. This internal knowledge is especially helpful when there is no cell phone coverage and thus no traffic apps on which to rely.

While most Caroline County residents will not take roads trips as seriously as, say, retired Arlington, Virginia, attorney Oscar Voss, who leads all Travelmappers with over 269,000 unique highway miles driven, ways nonetheless exist to participate locally. There are 27 numbered state highways that traverse the county, either in part or in full; the coordinates of each are provided turn by turn on Travelmapping.net. Since there are close to 500 Maryland roads displayed there, I have saved you the legwork of clicking on every single one of them should you desire to drive the Caroline County routes before your newfound addiction subsequently takes you into adjacent jurisdictions. Without further ado:

Route 16 (Hickman to Preston)
Route 287 (Sandtown to Goldsboro)
Route 302 (Templeville)
Route 304 (Bridgetown)
Route 306 (Houston Branch Road near Federalsburg)
Route 307 (Federalsburg to Williamsburg area)
Route 308 (unsigned; outskirts of Federalsburg)
Route 311 (Marydel to Goldsboro)
Route 312 (Baltimore Corner to Downes Station)
Route 313 (Baltimore Corner to Federalsburg)
Route 314 (Whiteleysburg to Greensboro)
Route 315 (Federalsburg)
Route 317 (Burrsville to Oil City)
Route 318 (Atlanta area to Preston)
Route 328 (Denton to Tuckahoe Springs)
Route 331 (Dover Bridge to Preston)
Route 392 (Reliance)
Route 404 (Adamsville area to Hillsboro)
Route 404 Alternate (Hillsboro)
Route 404 Business (Denton)
Route 454 (Templeville to Marydel)
Route 480 (Greensboro to Hillsboro)
Route 485 (unsigned; east of Hillsboro)
Route 577 (Federalsburg to Reliance)
Route 578 (Harmony to Bethlehem)
Route 619 (Denton)
Route 817 (Preston)

The locations in parentheses are rough approximations only and included merely to assist you in efficiently planning your journey. I will leave it up to you on how to plot your exact itinerary, especially in such a way that your family does not quickly conclude you have lost your mind and are wandering aimlessly in the middle of nowhere. Do some advance research and figure out some recreational stops along the way!

I hope that you will consider joining Travelmapping.net so that one day you will be honored as a distinguished viatologist, cartophile, or better yet, a Roads Scholar. In the meantime, know that members around the globe who use the website must undoubtedly criss-cross Caroline County in order to complete their quest; if you are a business owner, non-profit operator, or participant in local tourism initiatives, reach out to this and other travel affinity groups to increase your brand awareness.