If you matched outdoor
You're planning around light and weather, in that order. Book a time of day that puts your main moment in good light (an hour before sunset flatters everything), and treat the weather backup as part of the venue decision, not an afterthought. Ask every venue the same question: "If it storms at 4 PM, where are my 100 guests at 4:15?" If the answer takes more than one sentence, that's your answer about the venue too. Our outdoor backup plan guide covers this in depth.
If you matched indoor
Your event depends on control: a presentation that needs working AV, a winter date, a formal dinner where the room's acoustics matter. Judge indoor spaces on the things that are expensive to fix later, like sound, lighting, climate, and how close the kitchen is to the tables. A beautiful room where toasts echo into mush is a worse choice than a plain room where every word lands.
If you matched both
You're in good company; this is where most weddings, reunions, and milestone parties land. The key is how the indoor and outdoor spaces connect. Guests should drift from lawn to hall without a walk, a shuttle, or a staircase bottleneck. When you tour, walk the actual path a guest takes from ceremony seat to dinner seat, and count the steps. At Lilac Hill that path is a few dozen feet; at some venues it's a parking lot.

