Reply To: Riddle: Which food has an option of 5 different Brochos?

I got it: Kiddush wine on the first or second night of Sukkos.

1. Hagafen

2. Mikadesh Yisroel V’hazmanim

3. Shehechiyanu

4. Layshev Basukkah

5. Hatov V’hamaitiv

all lichatchillah