The history of computing has always been a fascinating topic for me, and as I have gotten older (and more nostalgic), I have found a hobby in vintage computing. Virtual machines running ancient operating systems and software have allowed me to revisit the days of exploring computers as a kid and young adult. Recently, my interest has wandered to old mapping and GIS applications. I have found or re-discovered software related to mapping, GIS, and locational data analysis that falls into the broad “abandonware” category. Some of these titles live on through modern versions which are still supported, and some have been long since forgotten. I thought it would be fun to share my experience of installing and using software that is 20 or more years old on modern hardware, as well as give younger readers some insight into how we used to learn and troubleshot software without Google π.
To kick Vintage GIS off, I will be taking a tour of Rand McNally’s TripMaker 1996. TripMaker was a commercially available software product and I would consider it a “GIS” application, in the looest definition of the term: it has a database of information that has geographic/location components and it provides tools to visualize and analyze the data.
I tried to install TripMaker on a Windows 11 machine, just to see if it would work. Unsurprisingly, it did not:


I tinkered with a few compatibility settings and the troubleshooting wizard, but still could not get it to run. That was the extent of the effort I put in to making this version of TripMaker work on a modern OS. In 1996, most people probably would have been using a computer with Windows 3.x or Windows 95. If you were in a corporate or educational environment, Windows NT 4.0 could have been used. This is the version I selected as I have found it to be more stable and easier to use in a virtual machine than 3.x and 95. Home networks weren’t really a thing in 1996, and Windows 3.x and 95 first make the assumption you connect to the internet through a dial-up modem, lacking some networking support out of the box as the typical home user wouldn’t likely have needed it. Getting these operating systems to connect to the internet on a virtual machine with a bridged LAN connection can require jumping through some hoops. NT 4.0 had a lot of networking stuff ready to go out of the box, like TCP/IP and the ability to obtain an IP address from my DHCP server. On first boot, my NT 4.0 machine immediately connected itself to my LAN and to the internet. I think that is impressive for an operating system that is nearly 30 years old!

Outside of app stores, not much has changed in 2022 with regard to the way software was installed in 1996. The CD contained a “setup.exe” and I ran it:


Installation went very quickly, taking just a few seconds with my modern CPU and fast NVMe hard drive; this may have taken several minutes or more in 1996 while files were written to the disk from the CD-ROM. Before exiting the installer, I was given the option to view the Readme file – this was (still is) a common way of giving a quick summary of a software package, highlighting some key features and tips to help a user get up and running ASAP.

When the installer exited, I launched TripMaker 1996 and was greeting with a welcome screen showing tips and hints for using the application:

I decided to dive right in and selected “Start Trip Guide.” This launched a wizard where I selected an origin, a destination, and stopovers points, a departure/arrival date, the preferred time window in which to drive, and a preference for the fastest, shortest, or scenic route:



The route was calculated almost instantly; so fast that some kind of progress indicator appeared briefly on the screen before the final result – a user in 1996 would not have had the benefit of today’s CPU and disk speeds and this may have taken several minutes or more to calculate:

The output shows a summary screen, and when that is closed, a split directions/map view occupies most of the screen real estate; this can be toggled to show only either the map or directions. The map allows me to zoom in and see the route at a large (zoomed in) scale, as well as surrounding attractions. The navigation tools yield a terrible UX by today’s standards – panning is only achieved through the vertical and horizontal scroll bars, and zoom in/out is limited to set intervals:

TripMaker also allows me to search specific locations for various attractions, with a predictive text input box:


TripMaker 1996’s database includes not only the geographic point, line, and area features to render a map, but also has rich (for the time) attribute data and images:


Not all features had photos or descriptive data, however:

An interesting feature I saw is a collection of phone numbers and other travel information – all stuff we would just Google today:

I mentioned earlier that I considered this “GIS” software, in the sense that it provides some basic tools one might expect in a modern GIS application: zoom/pan control, map layer toggle, legend, scale, etc., as well as some analysis tools that leverage the data within. The features are very limited, but this software does solve a navigation problem for the user. Multiple aspects of a route can be planned in a very short amount of time compared to the most common route planning method at the time, paper maps. There is no ability to import custom data, and the included data files were a binary type and not referenced in the documentation, so attempting to use this software or its packaged data for anything outside of the scope of route planning may be difficult. I think Rand McNally’s TripMaker kinda falls between a GIS application and an encyclopedia application, which were popular at the time.
Before I close, I want to highlight the importance of the “Help” menu. I am a proponent of RTFM (it usually never steers me wrong), and that might be because 30 years ago, the documentation that shipped with software was sometimes the only resource available to learn about and troubleshoot that software. Windows had (still has?) a built in help system that applications could leverage, and it would deliver documentation in a familiar and standardized way. I spent many hours reading through menus like these on hundreds of applications over the years:



Thanks for reading! I have more old or abandoned mapping and & GIS software to explore installed on various operating systems, so check back here in the near future for some more Vintage GISβ’ – I’ll take a look at some software that was more widely known in the GIS world like ArcView and MapInfo, some less popular GIS software, and mapping software that was geared towards the home PC user.
P.S. if you’re curious about what TripMaker looks like today, check it out: tripmaker.randmcnally.com
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