If you are looking for outdoor, winter ice skating then Pound Ridge Town Park pond, which is only a 5-mile drive from New Canaan has frozen over and was full of skaters and hockey players when we visited. The Pound Ridge Recreation Department confirmed the pond is open for unsupervised skating until 10:00pm daily.
We didn't have our ice skates with us, so instead took our dog on one of the long trails. It was really beautiful walking amongst the woods and because it is a paved walkway then you don't have to worry about soggy, walking conditions or evil deer ticks.
The mission of the Pound Ridge Recreation Department is to create and promote recreational, cultural and play opportunities for all town residents and to enrich their lives by preserving and enhancing the town's parks and natural areas. At the Town Park, there are ball fields, tennis courts, delightful playgrounds, swimming pools, as well as benches and grills for picnicking. Other activities, such as exercise programs, bridge group, toddler art, little league, tennis, basketball, and other sports are open to all ages.