If you change to a longer one, your arms would be more out-stretched if i visualize correctly.
One way is to get an extension stem to increase the height so that your body don't need to lean forward that much. In this case, you have to adjust the stem vertically. Coupled with ergon grips, your palms shouldn't be that easily numb. The extension will also allow the rider to have more forward reach for a more aggressive riding position if needed, and can be easily adjusted.
The picture above shows more horizontal reach rather than vertical.
Mostly on road. What bicycle are you cycling? You can always join your respective bicycle brand cycling group on Facebook and meet them up. Tern, Brompton, Tyrell etc have their own events, activities and round island rides.