The economics of transportation pricing is a fascinating topic that spans multiple semesters of university-level courses. However, the result of many sensible policies often leads to unique and beneficial tricks. One of which is the Amtrak free stopover trick.
Say you’re traveling from DC to Boston and want to visit Baltimore, Philadelphia, NY, and New Haven along the way. With a multi-city ticket, you can do just that. And as long as you spend less than 24 hours in each city, you’re only charged the price of the end-to-end journey… effectively making each stopover totally free. Prices typically look odd and nonsensical for the individual segments, but the sum is indeed the same as the direct one-way.
Want to spend more than 24 hours? Book the train one stop along the line (e.g. Philly to Newark, Newark to NY the following day, then NY to New Rochelle, etc.).
It’s a great way to see multiple cities in a region at once or meet friends for lunch, especially if you already have to make the end-to-end journey.
Note: On long-distance routes only served by one train each day per direction, stopovers don’t work since the layover time would be 24 hours. Also, all segments must be booked for the same class of service, so you can’t book an Acela for one leg and regional for the next; it must always be the same fare class for the split fare to work.