An adaptive ambulatory support includes a shock absorbing and pivoting tip assembly attached to the staff of a walking aid, such as a cane, crutch or walker. The shock absorbing and pivoting tip assembly includes a shock absorber sandwiched between a lower portion and an upper portion. The shock absorber may be a bendable spring or elastic material. The tip assembly enables the shaft of the walking aid to dynamically pivot without the loss of adherence of the lower portion to the floor surface and simultaneous provides the adaptive shock absorbing capability in any angle during ambulation.