If you only remember one thing: dead, broken, cracked, or hazardous limbs can come off any day of the year. Everything below is about structural and maintenance pruning on healthy trees, where timing affects how the tree heals and what pests it attracts.
Oaks: prune in the dormant season, roughly November through February. Maryland has oak wilt and a growing list of oak diseases spread by beetles that are drawn to fresh wounds in warm months. Winter cuts seal before the beetles are active. Skip April through July on oaks unless a limb is a hazard.
Maples, birches, and elms: also dormant season for structural work, but be aware maples and birches bleed sap heavily from late-winter cuts. It looks alarming and doesn't harm the tree. If you'd rather not see it, prune them in mid-summer after the leaves have hardened.
Flowering trees like dogwood, redbud, cherry, and crabapple: prune right after they bloom. They set next year's flower buds on this year's growth, so a winter trim removes the show. Crape myrtles are the exception and get pruned in late winter, lightly, never topped.
Evergreens and pines: minimal pruning, and only in late winter or early summer. Pines can't regrow from old wood, so cuts have to be made carefully at the candles or the branch collar. Arborvitae and hollies for hedging get shaped in early summer.
One more rule that applies to everything: don't let anyone top your trees. Topping leaves stubs that rot, produces weak sprouts that break, and shortens the tree's life. A licensed Tree Expert reduces a tree's height by cutting back to lateral branches, which keeps it structurally sound and looks like a tree, not a hat rack.