numb...while riding??

I had the same problem last year. Some of it had to do with the pedals I was using. I was using my eggbeater mountain bike pedals (small surface). They worked well for the first 50 miles of any ride, but longer rides would result in numbness of my toes. I also pulled my cleats more towards the back of the shoe. I had them as far forward as possible which seemed to add to the toe issue. Lastly, I had my shoes on too tight.

Yup, I've got the same problem...but only in the right foot.  And I use a large platform pedal system, too (Time RXS Carbon)...so it's not my pedals.  My cleats are positioned correctly, I wear a cycling shoe with a wider toe box, I've had a proper bike fitting, I always wear Smartwool cycling socks when I ride...so it would seem I'm doing everything "right", yet I still have the numbness.  So I'm beginning to think that it might be an actual issue with my foot itself....most likely a neuroma, or some other nerve-related condition. 

Consider getting a bike fit. It can be the way your foot interacts with the pedal and position of everything.

My foot has similar thing but only after 4 or 5 hours of riding when it is hot and it goes from numb to complete horrible pain if I continue to to ride another hour or two. It has happened in different shoes, different pedals and different bikes, which eliminates down to my feet. I had custom orthotics made for my cycling shoes as they are different than running orthotics. I rec'd them late and about 10 days before my Ironman so I haven't ever used them as I went with the nothing new on race day them as orthotics could effect my leg, hip and knee alignment.

I have true Mortons foot with my first metatarsal is very short and it's worse on right and what happens is my metatarsals effect the nerves in my foot when I ride long and it's hot probably because my feet slightly swell.

I had this problem when I first started up riding....then decided that since I'm going to do mostly sprints right now I'll get my feet used to riding without socks to speed up the transitions.  and whaddya know?  no more foot or toe numbness.  Apparently my socks were just too small for my feet, which is either going to compromise the circulation down there or squish bones into nerves.  It might be a simple, and cheaper fix to try first than getting a real fit.

Same issue here.  Starts at mile 55 on my right foot and then about mile 70 on my left.  Mine goes beyond numbness and actually becomes a sharp shooting pain from ball of foot up to tip of big toe.  If I soft pedal for a bit it goes away, only to come back after a bit.  I am reluctant to put otho's in as we pay a lot of money for carbon soled bike shoes and carbon pedals and titanium bikes....all for the stiffness to maximize power transfer.  Seams counter productive to add something to absorb some of this stiffness (in turn stripping power).  Probably over analyzing here, but I'm curious to find solutions which don't involve otho's.

If I have numbness I use it to practice more on proper cycling technique.  I try to go the full cycle and put an emphasis on the 3-6 oclock as well focus on the pull up6-12 oclock, that take pressue off my feet on the 12-6 oclock and alleviates numbness.  I will do this 5 minutes on 5 off, if that makes sense.

I am looking at better inserts for the shoe.

I get numb toes, too. And that's with a proper bike fitting and shoes.

I didn't like the feeling during the bike, but it was really a bummer to hop off the bike for the run with numb toes/feet.

Then I happened upon a way to get ride of it. I curl my toes (inside my shoes of course) for 30 to 60 seconds. The numbness goes away...for a while. I just make sure I do it when I'm about half a mile of T2. Then I can hop off the bike with NO numbess in my toes. YMMV.

JC