Discover Boston’s History with the Old Town Trolley – Roaming Historian

On our first trip to Rome, we booked our first “hop-on, hop-off” bus adventure. That was a big double-decker bus with an open top and, although it couldn’t get to many of the inner parts of the city, it gave us a good idea of the city’s layout and saved some steps. Since that first experience over a decade ago, Jon and I will occasionally book a hop-on/hop-off bus when our fancy strikes. As we prepared for our Boston trip, I thought it would be a wonderful way to see the city. But I wasn’t sure how feasible it would be for Jon—who is mobility-challenged and uses a folding mobility scooter when we travel. Thankfully, I found Old Town Trolley Tour and they boasted of fully accessible trolleys so that Jon and I could ride around the city in comfort with ease.

Boston is a treasure trove for history lovers with a documented past dating from 1630. You can see many important places from colonial times through the 21st century. A hotbed of revolutionary fervor, there are many important places from the American Revolution in Boston and, of course, the Freedom Trail is a “must-see” for American history enthusiasts. Besides history, Boston boasts amazing food (North End’s Little Italy is a good place to gorge yourself), fabulous sea views, gorgeous art and architecture, sports, culture and much more. With so much to see and do—spread out over the city—the trolley was a great way to navigate the city.

What is the trolley tour like?

The route is about 13 miles long and takes about two hours from start to finish. Depending on when you go, the trolleys generally run daily and come around about every 20 minutes. Throughout your ride, the drivers/guides provide rich commentary about Boston, its history, and its culture. Each time we hopped on, we had a different guide but I noticed that they all had the same basic bullet points for the stops, so they are uniformly trained on the stops and Boston’s history. Between telling histories, stories, tales (some of them tall), the drivers played fun soundbites, which added to the jovial atmosphere. Twice I rode past Cheers bar and both times the guide played the Cheers theme song as we neared the stop. I loved looking out the window to see people on the street smiling from ear to ear when they heard the familiar song. One person even belted out the familiar refrain, “you want to be where everybody knows your name.” She was so filled with joy that I, too, was smiling from broadly.

It…