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If you are coming from Enfield, and just want to party on a train for 2 hours with UConn fans, take a mid-afternoon train from New Haven. There are a few benefits to this:
1) By the time you get to the station in NH, there should be parking in the main garage.
2) You have a shorter drive, and more time to party on the train.
3) You have 2 hours to sober up on the train ride home.
4) You do not run the risk of falling asleep on the way home and sleeping through your stop since New Haven is the end of the line (do not underestimate this as a reason).
If you prefer trains that were made in the last 30 years and don't smell like urine, you can take I84 west to I684 south and park at any of the stations right after you get on 684 (Croton Falls, Goldens Bridge, Purdys, Katonah). The drive is a little longer and the train ride is a little shorter, but the trains are a lot nicer.
LOL, thanks for the advice. Any idea how late the parking garage is open at New Haven?