Bennington parents have employed a range (and often a combination) of strategies for arranging supervision for their kids. Most (although not all) people who bring their children have also brought their spouses. In families with small children and two musician parents, the parents sometimes arrange each to be coached part time, so that they can each spend some time playing their instruments and some time playing with their children. Some parents have brought full-time babysitters with them; others prefer to hire local babysitters, whether full-time, part-time to give the parents a break, or for specific occasions such as concerts. The Early Childhood Center can also provide childcare in the mornings during weeks 1 and 2.

In practice, these logistical challenges are substantially mitigated by the ability of parents to pool resources. Since children at Bennington generally prefer to spend most of their time together, a single active care-taker often suffices for a group of children who mostly entertain each other. In the child-heavy weeks, parents are usually able to organize and undertake activities as a team, to take turns watching one another's children, and to pool for babysitters. Moreover, the safe and stimulating atmosphere of Bennington College allows older children to play and explore on campus with minimal supervision (though of course their parents remain responsible for them). At various times, groups of older children have collaborated to babysit younger ones.

Parents curious about bringing their kids to Bennington are encouraged to visit the Discussion Forum to pose their questions to experienced Bennington parents.