My first contest experience was in the 1969 ARRL CW Sweepstakes.
On a challenge from a school classmate who was also a ham, I entered the contest. It was a "one-on-one" competition between the two of us. At the time, I was still a Novice running only 60 watts from my Knight-Kit T-60 and limited to only 3 or 4 crystal frequencies.
Going none-stop all weekend, I managed to complete around 27 QSOs. My challenger, who by this time had upgraded to General and had a rig with a VFO, trounced me by making about 60 QSOs.
Despite this, the contesting bug had bitten. Fortunately, I now routinely complete more than 27 QSOs in the Sweepstakes!
After years of solo contesting, I've now joined a contesting club - the South East Contest Club (aka SECC).
I invite you to visit the club's web site to learn more about it and ham radio contesting.
South East Contest Club web site