Injury to a tendon/ligament on the top of my foot?

I noticed one and then another foot get a sort of sprain. There's a tendon or ligament that runs from my big toe up the top of my foot to my ankle above my arch. It hurts to walk on it but I can place static pressure on it. Barefoot aleviates the pain while wearing any shoes hurts. The pain radiates from the center of that tendon/ligament parallel to the center of the arch. I feel my toes stiffening from this and cracking them helps.

The tendon you are referring to is that of extensor hallucis longus (EHL).
It sounds like this pain and stiffening is a result of Hallux Limitus.
The joint of the big toe (1st metatarsophalangeal joint or MPJ) bears a tremendous amount of force (6 x body weight) during regular daily activity.
If its range of motion in dorsiflexion is reduced, it severely limits the ability of the MPJ to distribute this force which is then transferred to adjacent sites (eg: the joints of the arch).
Alternatively pain such as this could be caused by damage to the Lisfranc Joint or a you suggested, soft tissue damage to a ligament or tendon. The chances of these occuring bilaterally (both feet) however are much less likely than hallux limitus.
Have a look at the sites below for more info and make an appointment to see a podiatrist for diagnosis and treatment options.
http://junctionpodiatry.com.au/media/pdf...
http://www.footphysicians.com/footanklei...
http://www.aafp.org/afp/980700ap/burroug...

All the best!

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