Oh boy. Unfortunately, there is very little in the way of public transit in Kent – and especially in South Kent, where we are. You have two options to get up here, both involve the train and then trying to get a taxi at the other end. The closest train station is in Harlem-Valley Wingdale. The other station you can aim for is Danbury. Both are on the Metro North line and you can find detailed information at the MTA website on arrival and departure times. We are not aware of any taxis from Danbury but you can schedule a pickup in HMV with Harlem-Wingdale taxi at +1 (845) 224-1893. Call or text, and definitely schedule in advance. It will be about $50 from the station.
For service in and around Kent itself, you can reach out to Litchfield County Livery, at +1 (860) 601-9143. We haven’t used them personally but they do provide travel services in the area.
Legend has it that there’s an Uber driver that will periodically appear on the app, but we’ve never seen it. Best to have a car if at all possible.