Prepare squash by washing, trimming ends, and peeling. Cut squash in half and then in half again longways. Scoop out seeds with a spoon and cut into chunks of about 1 to 1 1/4 inches.
Make enough simple syrup to barely cover your prepared squash in a ratio of 1 part sugar to 4 parts water. (For a medium-large saucepan - dissolve 1 cup sugar into 4 cups water) Add 2 packets of unsweetened cherry drink mix and optional cherry concentrate if desired. Simmer while stirring to thoroughly combine & completely dissolve sugar.
Add prepared squash to cherry syrup until squash pieces are just barely covered by syrup. Simmer 30 minutes until squash is lightly soft. Remove with slotted spoon into colander.
Place cooked squash onto dehydrator trays, spacing evenly without pieces touching each other. Place trays in dehydrator set to 135 degrees. Rotate trays every couple of hours for even dehydrating. Gummy chews are ready when they are soft and lightly tacky but no longer sticky.
Store in glass jars in the refrigerator and consume within about 30 days or so.