November 22, 1998: Thanksgiving in 1998 wasn't until the 26th, but Happy Thanksgiving in the present day.
We were pushing hard on the new Maps & Directions feature. I thought it was a partnership with Mapquest, but Wikipedia says Mapquest didn't become Mapquest until 1999, so perhaps it was with the proto-Mapquest.
For the graphic promo, we used a segment of an actual Maps & Directions map with "you are here" artfully (*cough*) superimposed. I did a few seconds of research and the intersection is East Hillsdale Boulevard and the 101 in San Mateo.
I don't think the location had any particular significance or hidden meaning, outside having a cloverleaf intersection and a bit of water for color:
which relaunched with a new design on July 14, 1998.
I printed screencaps and saved them. 20 years later, I'm scanning them
in and posting them with a little commentary under the tag #20YearsAgoOnAOLcom.]