For peak-season weekends in the Twin Cities or Madison June through September — quality entertainment books out 12 to 18 months in advance. If your wedding is during peak season and you’re reading this more than a year out, you’re in good shape. If you’re six months out and haven’t booked yet, reach out sooner rather than later — availability narrows quickly, especially for Saturday dates. Off-peak weddings, including Minnesota and Wisconsin winter celebrations, typically have more flexibility, but it’s still worth locking things in early.