09/15/2026
Early October in Connecticut. Timber pergola, w**e barrels, burgundy dresses, and about three weeks a year when the light up there looks like this.
October was my busiest month of the year, every year. In Sarasota it's the tail end of hurricane season, and most couples I talk to here are looking at January, February and March instead.
Different shape to the calendar, not a better one. New England gives you May, June, September and October and you're gambling on all four — but when it lands you get what's in these frames, and nothing down here looks like that. The Gulf Coast trades the gamble for a longer window: November through April holds pretty reliably. You're just not getting a sugar maple behind you.
The catch down here is lead time. Good venues go twelve to eighteen months out for those months, which means someone getting engaged this Christmas is already looking at early 2028 for a peak Saturday.
If you're engaged and thinking you have plenty of time — for a winter Sarasota wedding, you might not. Send this to whoever's helping you pick the date.
