Start with The High Line for a quick, low-cost reset before you head out. If you’ve got a bag, keep it light and do this as a simple stroll from the 14th Street or 23rd Street access points; late afternoon is a sweet spot because the light is nicer and the crowds thin a bit compared with midday. Give yourself about 45–60 minutes, then drift down toward Chelsea Market for an early dinner — it’s one of the easiest places in the city to eat well without getting trapped in a long sit-down meal. A $15–30 budget goes a long way here; grab something fast from Los Tacos No. 1, Los Mariscos, or one of the noodle/sandwich counters, then head east or uptown depending on how much time you have.
If your train is later and you want a calmer pause before Penn, swing by Bryant Park for coffee or a snack. It’s a very efficient “buffer zone” between the chaos of downtown and the station, and it’s especially good if you want to kill 30–45 minutes without feeling rushed. Blue Bottle Coffee and the kiosks around the park are handy for a quick caffeine stop, and the seating is usually easy enough to find if you’re not picky. From there, it’s an easy walk or short subway ride to New York Penn Station — just don’t cut it too close, because evening trains can mean lineups at the board, platform changes, and a little extra time finding your track.
From New York Penn Station, take the Amtrak Northeast Regional or Acela to New London Station — this is the fastest practical way to do the trip without paying absolute peak-premium prices, especially if you book a Northeast Regional seat in advance and aim for a departure around 5:30–7:00 PM. The ride is usually about 2.5–3.5 hours depending on the train, and the sweet spot is getting to the station 30–45 minutes early so you can grab water, confirm the platform, and avoid the last-minute scramble. If you’re trying to keep costs down, Northeast Regional is usually the better value; if the fare gap is small and time matters most, Acela is the faster splurge. Either way, expect a straightforward trip with no transfer headache — just check the track board and be ready to board quickly when it appears.
When you roll into New London Station, keep the arrival simple: either walk if your lodging is close to downtown or take a short taxi/rideshare for the easiest final hop, usually 10–20 minutes depending on where you’re staying. If you arrive with a little daylight left, the area around the station is compact enough that you can orient yourself without much effort, but the main goal tonight is to get checked in and settled fast. That’s the cleanest ending to a budget-conscious, time-efficient travel day: one easy pre-train meal, one fast rail ride, one short last transfer, and you’re done.