Canaan is in the Litchfield Hills, otherwise known as the Connecticut Berkshires, in northern Litchfield County. Do not confuse Canaan with New Canaan, a much larger town which is well to the south in Fairfield County.
Canaan is a township that includes the villages of Falls Village and South Canaan. North Canaan, a separate township, separates Canaan from the Massachusetts border. However, local usage is to treat North Canaan as if it were a part of Canaan, so this article includes North Canaan, too.
US Route 7 traverses the township from north to south. US Route 44, an east-west route, meets Route 7 in North Canaan. To get from points south, including New York City, take Route 7 North. To get from the Massachusetts Berkshires, take Route 7 South. From Hartford and other points east, take Route 44 West.
There are buses that travel up and down Route 7, transporting people to and from New York City, Vermont, and many towns in between.
There is a historic station in North Canaan which is worth looking at. However, it stopped operating a long time ago.
A car or other vehicle is most useful for getting around.
As you can see from the photos on this page, there are some charming buildings in the townships of Canaan and North Canaan. Since if you are going further north to the Massachusetts Berkshires, you will probably be traversing this area, in any case, why not enjoy them?
The Berkshire Hills of Massachusetts are an obvious place to go next, or you can drive around other areas of the Litchfield Hills. For example, the town of Norfolk is immediately to the east of Canaan via Route 44.