This is an delicious Autumn-y popsicle! The recipe is from Locopops, a gourmet ice pop place in North Carolina, but I found it on Bon Appetit's website. The recipe said it made 12 popsicles, but for me it made about 7 large ones.
Combine first 6 ingredients in saucepan. Bring mixture to boil, stirring until sugar dissolves. Reduce heat to medium; simmer until mixture is reduced to 3 1/2 cups, 20 to 25 minutes. Strain into 4-cup measuring cup; cool to room temperature. Stir in vinegar and vanilla. Pour into twelve 1/3-cup ice pop molds. Insert ice pop covers and sticks; freeze overnight.