If you're looking for a meeting place or a good stop around ½ or halfway between New York and Bridgeport, you can try Greenwich, CT, which is almost an hour northeast of New York, or about half an hour southwest of Bridgeport.
About ¼ or a fourth of the way, you can stop at Lambert Houses, NY. This is about 17 minutes northeast of New York.
About ⅓ or a third of the way, you can stop at New Rochelle, NY. This is about half an hour northeast of New York.
About ¾ or three fourths of the way, you can stop at Norwalk, CT. This is almost an hour northeast of New York, or about half an hour west of Bridgeport.
If you drive straight through without stopping at all, the total distance is 62 miles. The distances shown above don't include local roads to get into each town, so if you're planning a long road trip, make sure you factor in traffic and road conditions, rest stop breaks, and interesting detours along the way. If you're in a rush, you can do the trip with zero stops, and your total travel time would be around 1 hour, 17 minutes.