If you're looking for a meeting place or a good stop around ½ or halfway between Ossining and Hillsdale, you can try Grand View-on-Hudson, NY, which is about half an hour southwest of Ossining, or about half an hour northeast of Hillsdale.
About ¼ or a fourth of the way, you can stop at Tarrytown, NY. This is about 11 minutes south of Ossining.
About ⅔ or two thirds of the way, you can stop at Spring Valley, NY. This is about half an hour west of Ossining, or about 14 minutes north of Hillsdale.
If you drive straight through without stopping at all, the total distance is 31 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 45 minutes.
