About ⅓ or a third of the way, you can stop at Tarrytown, NY. This is about 13 minutes south of Ossining.
About ⅔ or two thirds of the way, you can stop at Nyack, NY. This is about half an hour southwest of Ossining, or about 13 minutes south of Haverstraw.
About ¾ or three fourths of the way, you can stop at Rockland Lake, NY. This is about half an hour southwest of Ossining, or about 9 minutes south of Haverstraw.
If you drive straight through without stopping at all, the total distance is 26 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 41 minutes.