Getting Around Boston
Boston's subway and trolly system is notoriously difficult to navigate by stroller, and you should expect to spend some time carrying your stroller up and down stairs or lifting it onto trains. The MTBA website has information about stroller/wheelchair access at specific stations
Boston Airport
Boston's Logan airport has terrific kids play areas in both the A and C terminal. Consider arriving early so that your child can stretch his or her legs before boarding your flight.