good thread-i was HS in the '80s and University in early/mid '90s. Timex triathlon watch was the bomb at the time-lap and reset function. I had one for 6 years-when the strap wore out -velcro bands were the thing to replace it with! before that in the '80's I used my mom's oven clock to track run times.
-a map and ruler did fine for checking run distances-if you went on trails where you couldn't check the distance on the car odometer. Race results for cross were stickers on a board-better hope that you saw them after the race or have your coach write 'em down! as mentioned, you'd go to the running shop to pick up race flyers and mail in your check.. I still remember talking to my buddies on the phone "hey did you get the results yet?" sometimes it took 3 or 4 weeks to get your results by snail mail. Discmans sucked for running-they skipped too much as previous posters mentioned;
If I did use music-I would roll with the '80s Sports Walkman-clunky but durable with 45 minutes of Van Halen on tape -it would last 6 or 7 miles -you would rarely run farther anyway;
Road races were fewer but much more competitive in nature-I would have to run 34 minutes or faster for 10 km as a junior to be top 3 in that age group-maybe be top 20 overall--10 years later the same time would often win the race!
I remember lot of hard running on the roads and track; Singletrack trail running was something you would do for kicks a few times a year in the fall. I would use a notebook/log for rough milage estimates and key track workouts; Half of the splits I would forget since I would be too tired by the time I wrote them down. I never trained by heart rate-rather by feel.
Runner's World was actually decent then. major source of race info prior to the 'net getting popular in the late '90s//
Good times and memories-ain't nothing wrong with delayed gratification!