Putting together, a plan begins, deciding on either destination or route. My first excursions were planned to follow a route. Steam excursions were frequent in the 1960's and 1979's. Add to that the Freedom Train, Chessie Steam Specials, Chessie Safety Express, and all the Southern steam specials. These were the mid 1970's and rumor had it that Southern was going to discontinue the Crescent Limited from Washington to New Orleans and turn it over to Amtrak. I decided to take the Crescent from Washington to Atlanta, which was its destination three days a week with extended to New Orleans on Tuesday and Thursday (I my have that wrong, but I am working from memory). Of course Southern kept it for a little longer before turning operation of the Crescent to Amtrak. So! I took the Crescent to Atlanta, spent the day, and return that night back to Washington.
I normally use both destination and route in combination to plan my trips. Looking at the Boston trip, I began with destination. Here, I plugged my home of Cary, NC with Boston being the destination. Amtrak's website, will take either the Silver Star or the Carolinian from Cary, NC to Washington, DC. From DC, they recommend the Northeast Regional, departing around 10:00 pm to Boston, an overnight train, with arrival in Boston around 8:00 am. Considering that a return trip begins at 9:30 with connection in DC after an overnight trip. It would be conceivable to do a single day in Boston as an excursion with sleeping overnight on the train.
In this one day trip to Boston, I set out to see what I could see. I lived in Boston in the 1980's. Part of that was in Cambridge and part was in Lynn, with my first months at the YMCA near Copley. I worked near the Copley Library. In fact, is next door to what is now Copley Place. It was under construction when I lived there.
Planning begins with starting point and destination, than layout route. In a trip from Car, NC to Boston, MA, we lay out two trains. Transfer can occur any where from Richmond, VA to Washington, DC. Richmond is nice: early off and early back on. Fredericksburg, VA limits what train to start on. Alexandria is good as is DC.
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