Great coffee
Great food/brunch
Fun pub with great food
Delicious French food
Outdoor Arts Festival Oct 6-7 will feature over 85 artists
West Point is 1 hr 15 mins to 1 hr 30 mins from Stamford by car on a normal day (depending on traffic, could be much longer and should check GPS). It is situated on the banks of the Hudson river. You can tour the grounds and grab lunch at nearby Cold Spring. Beautiful area.
High-end shopping and a range of places to eat
Great theater for a rainy day
Great tacos, fun vibe