Leah McCann Smith | Writer & Editor

This past weekend, I had the pleasure of visiting the lovely and serene town of Boston, Massachusetts. My expectations were set to an image of cobblestone taverns from the 1700s, history-entrenched town halls and churches still standing proud in the middle of the bustling city, and cleaner, nicer, narrower streets than those of New York, where I currently reside. Aside from the “you have to walk the Freedom Trail and try the Italian food,” my knowledge on the city was pretty minimal—it was my first time there. With high ambitions and packed itineraries, we (my S/O, Brian, and his dad, Tom) were ready for an adventurous three-day visit.

Brian and his dad had previously been to Boston, but their last visit 12 years ago meant we were all experiencing the city together with fresh eyes—and, for me, a hopeful heart that the great things I’d heard would live up to my expectations. Stepping off Amtrak train 190, I smiled at the prospect of the weekend ahead.

Read about day one, two, and three of my Boston adventures.