Upvote:7
There is an Amtrak service from Windsor to either New Haven State Street Station or New Haven Union Station, the train runs throughout the day. Times can be checked for specific days using the Amtrak route finder, example times for tomorrow:
The location for the stations:
Amtrak Windsor CT Station - 41 Central Street Windsor, CT 06095-2908
Amtrak New Haven State Street Station - 259 State Street New Haven, CT 06519
Amtrak New Haven Union Station - 50 Union Avenue New Haven, CT 06519-1754
Using the fare finder, a one-way value fare for one adult is $9.25.
Upvote:8
For getting around New Haven, as explained on the CTtransit fare schedule, you can purchase an unlimited local rides one-day bus pass for $3.50 on the bus by pressing the "Get All-Day Pass" button. As explained elsewhere by CTtransit, you can also purchase it in advance by mail or online, and 10-ride local tickets can also be purchased at various Stop & Shop supermarkets (including 1095 Kennedy Road in Windsor). That may be plenty; I haven't been to New Haven in over half a decade now, but I didn't find anything of interest beyond the Yale campus and the waterfront.
As for getting from Windsor to New Haven, the bus is incredibly inefficient. There are half a dozen trains a day in each direction, and advance-purchase tickets are under $10. It isn't especially scenic, but the bus is much less comfortable and takes more than twice as long.
Upvote:13
The Hartford Line train works well. Note that besides the Amtrak schedule posted by Danill, there is additional train service on this line provided by the State of Connecticut (CTrail). The same ticket can be used on either service (with the special exception of the Amtrak Vermonter). Full details and a combined timetable are at https://www.hartfordline.com/.
The most economical way to get to the train station is probably a local bus; they are operated by CT Transit. Your closest major stop seems to be the Poquonock Park & Ride, just a couple blocks from your hotel.
From the local system map (also linked from https://www.cttransit.com/ but only shows up if your browser window is sufficiently wide), it looks like you could take Routes 32/34/36 to the train station in Windsor.
But another option would be to take Route 30 which runs to downtown Hartford and stops at Hartford Union Station. This will give you more train options, as there are some trains that run only between Hartford and New Haven without continuing to Windsor.
Make sure to check bus schedules because some routes run infrequently or only on weekdays.
You can buy a single trip or day pass on the bus with cash (change will not be given). There is also a contactless Go CT card, which is convenient to use but a bit difficult to obtain except by mail.