6. Cortland

The next small town you may want to move to after retiring is Cortland. Home to SUNY Cortland, this place boasts a dynamic academic atmosphere and a friendly community spirit. Moreover, it offers a strong sense of belonging, affordable living costs, and a balance between outdoor exploration and cultural engagement.

In other words, Cortland is one of the best and most affordable Upstate New York towns to live in your golden years. Walking across Main Street means enjoying its many boutiques, cafes, and a thriving arts scene. Outdoor enthusiasts can revel in nearby parks and trails. If you don’t have a hiking backpack, here are some great options to choose from.

According to recent data, the median house price in Cortland is $148,750, while the average rent is $985. This is good compared to other Upstate New York towns.