Never been up that hill, and I doubt I could do it today without walking that steep stretch.
Until 2011, my lowest gear was 38-23, which was pretty standard for a road bike purchased around 2000 (52-38 in front, 11-23 in back). There were some climbs from my house I could only get up by standing, such as the climb up Chesterfield Rd, and then just barely. (I croaked the first time I did it on a
ride with PG.)
I'm a lot older and slower now. I have 34-32 for my road bike and 34-34 for my gravel bike. And when I've done D2R2 rides with the latter, there were times I wished I had an even lower gear, as I had for the first couple of D2R2 rides that I did with mountain bike gearing.