Does it have to be the Catskills or are you willing to go a little further west? The Finger Lakes region in upstate NY has been ranked the #1 wine region in the U.S. a few times, with Canandaigua being the largest wine producing region in NY state. There are over 100 wineries in the area, tons of wine tours, and the area consists of 11 small-ish lakes which makes for a beautiful setting with outdoor activities, boat tours, etc. I got married in Canandaigua a few years ago and had my reception at NY Kitchen, which is a great spot for cooking classes, wine tasting and pairings, or just a good dinner.
There's a new hotel called the Lake House opening right behind NY Kitchen in mid-August. The hotel was formerly called Inn on the Lake (its where my wedding guests stayed), and they tore it down and have been building this beautiful new hotel in its place over the last two years. I was sad for them that Covid-19 will likely impact their opening year. DH and I will be visiting for our anniversary in September!
Canandaigua is a quaint town with an active Main St area and would be considered "country" by those of us who live in larger cities like Rochester or Syracuse, but there are more remote areas around the Finger Lakes as well that offer similar wine tours and activities - I would also look at Skaeateles or Geneva.
I’ll check it out.
