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It is possible to tame a chipmunk if you get it when its very young(under 4 months). A breeder may have had time to tame the babies but if not if the babies parents are tame it will be easier to tame them.
You must never pick a chipmunk up by its tail.
As part of its natural defence mechanism against predators the tail can break of quite easily so that the chipmunk can escape. Some how this happened to our chipmunk, Max, we arent sure how as we just found her tail on the floor after she had been out for a run. If this happens dont panic the wound usually heals quite easily and the dry part eventually drops of the end. The chipmunk will be fine and continues its life not seeming to notice.
Only hold the tail where it joins the body, and support the body weight with your other hand, with the second and third fingers over the chipmunks shoulders.
If you do want to hand tame your chipmunks the easiest way is to let your chipmunks out of the cage in a room (making sure doors, windows etc are closed and any fragile ornaments are out of reach) Hold a treat(sunflower seed or monkey nut) on your palm and let the chipmunk see it then be very patient and quiet and the chipmunk will eventually sit on your hand and eat it. Outside the cage, they will jump on the highest point of their owner's body, such as a shoulder or head, but won't stay there for long. If you walk by a tall piece of furniture, the chipmunk will want to jump off you to investigate this newest "tree". It is best if you restrict their out-of-cage time to only one room. Chipmunks are less trusting with people they do not know. They can be friendly to strangers that are quiet and move slowly, but they are never as bold with strangers as they are with their owners.