As a fellow NYer who moved to your neighboring town of Southbury, Woodbury is good for food but for anything else you need to go to bigger towns like Danbury or Waterbury. Woodbury definitely does Christmas right, on Christmas Eve they light lanterns all down Main St, we drive through every year and if there is a little snow it looks like a Hallmark Movie. If you have kids as others have stated the Hollow is a great park, it if you have younger kids you might want to check out the playgrounds in Middlebury, they equipment is better for toddlers. New Morning Market is like a small town Whole Foods, so if your on a special diet you might want to check it out. Rustic Charm makes really nice home decor, you picked the right town if your into antiques. The school system is great, my husband attended the high school there and really liked it. Overall you picked a good town. Welcome to CT, message me if you ever want to talk :)