JCNeumann

+1

i had a very similar issue with ice skates. Played hockey for 35 years, and always had my toes turn numb by the end of a game. Started speed skating a few years ago, same issue and never thought much about, as I've always liked skates very snug fitting. I commented about it to one of club coaches in the "post-skate rehydration sessions" aka beers, and he said "relax your foot, and focus on putting pressure on the whole sole". D'oh!!!!!

It took me a few months to implement this, and lots of focused training, but numb toes are gone. Nice bonus is that the skating stride is very similar to pedaling, so it made a significant improvement when I ride. Not so much speed, but comfort and control.

+1000

the comment on nerve pinching. Get that checked out ASAP, as it will get much worse before it gets better. There are occasionally non-surgical solutions if it isn't too bad. This issue can create all kinds of havoc beyond your toes.

RT

This is it. Who thought riding a bike could be done so wrong for so long? My pedal stroke is in rehab right now, and it is not an overnight thing - you really have to focus.

FWIW, I started a foot discomfort thread a while back and have updated it from time to time. The latest remedy that has worked the best, better than anything else I have tried in 20 years, is toe separators. They cost about $8.00 at Walgreens or drugstore.com, and I sleep with them. This allows my foot to relax in a normal, i.e. un-cramped position. Not an overnight thing, but again, more like a rehabilitation for a foot that has been abused for so long.

For reference.