Almost 400 years old, Boston is home to many of America’s “firsts”— the country’s first subway, chocolate factory, public park, public beach, lighthouse — the list goes on and on. While the city holds a special place in American history, it also holds a special place in Road Scholar’s heart — this city is where you’ll find our main campus!

Perhaps one of the best ways to trace the history of Boston (and we mean that quite literally) is along the Freedom Trail, a two and a half mile route that connects 16 nationally-significant historic sites. Our exploration begins at the Charleston end of the trail, where the USS Constitution and Bunker Hill sit. Boston is known as the birthplace of the American Revolution, and this area played an integral part of that history. Right in front of you is the Bunker Hill Monument, built to commemorate one of the first major battles in the Revolutionary War. The first public obelisk in the country, Bunker Hill was the nation's tallest memorial prior to the construction of the Washington Monument. Docked nearby is the USS Constitution, the oldest commissioned warship in the world still afloat. Nicknamed “Old Ironsides,” her story illuminates much about the U.S. Navy during the nation's first 100 years. Learn more about this majestic ship here.

Follow the Freedom Trail across the Charles River to the North End, one of the oldest Italian American neighborhoods in the country. While this neighborhood covers roughly only one square mile of land, it’s packed to the gills with history and personality. Originally settled by Puritans, the North End’s proximity to the waterfront and downtown markets made it a hub for both local and transatlantic commerce. As one of colonial Boston’s first residential areas, it was also once home to some of the town’s most elite families, including the Reveres. Let’s head to North Square, a little plaza along the trail where we can visit Paul Revere’s home. Built in 1680, this house is the oldest livable house in downtown Boston. Just a few steps further is the Old North Church, a building made famous by American poet Henry Wadsworth Longfellow.

 One if by land, and two if by sea;
And I on the opposite shore will be,
Ready to ride and spread the alarm
Through every Middlesex village and farm,
For the country-folk to be up and to arm.

While several creative liberties were taken during the writing of the poem, “The Midnight Ride of Paul Revere” secured Old North Church and Paul Revere a lasting place in American history and folklore.

Although the North End has seen many changes over the years, it’s impossible to ignore the neighborhood’s rich cultural legacy as you wander these cobblestone streets and chat with the residents. It’s also impossible to ignore the culinary offerings in this part of town with bustling restaurants and bakeries everywhere you look! Yet even many of these spots boast an impressive history in addition to an impressive menu — pop into Caffé Vittoria (opened in 1929) for a cinnamon-topped cappuccino, peruse scrumptious treats from 24-hour Bova’s Bakery (a family-owned spot that opened in 1932) or check out America’s oldest hand-carved bar in Amrheins Restaurant. You can even enjoy a pint at Green Dragon Tavern, an establishment opened in 1684 and once frequented by John Hancock and Paul Revere. It's said that Revere’s plans for his infamous ride were overheard at this very bar!

Want to bring a taste of the North End home with you? Pasta lovers should head to Bricco, where they can dine on scrumptious dishes in the restaurant or shop at the attached Italian grocery store. Coffee and tea addicts will find a slice of heaven in Polcari’s Coffee, a shop that’s been family-owned for over 80 years. Meet the current owner and see for yourself!

Further down the trail is the Old State House, a remarkable historic contrast to the skyscrapers that surround it. Having survived the Boston Massacre, the Revolution and a serious fire, the Old State House is the oldest public building in Boston. Look up at the balcony, the very spot where the Declaration of Independence was first proclaimed in July 18, 1776.

As we make our way deeper into the city, let’s stop and grab a drink at the Omni Parker House. Built in 1855, this hotel has welcomed a slew of famous visitors, including Charles Dickens and Ralph Waldo Emerson. It’s also employed several people who would later become famous — Ho Chi Minh once worked as a baker here, and Malcolm X was a busboy. It is also the place where the Boston cream pie was created!

Next we cross into the Boston Commons and Public Gardens, another stop on the Freedom Trail. Established in 1634, the Common was created as America’s first public park, a practical yet pastoral maze of walkways built for crosstown travel. In 1837, the land was split into two parks, and a portion of the plot became America’s first public botanical garden. This Google Earth link drops you in the middle of the garden, where you can take some time wandering among the tulip patches or watching Swan Boats glide by.

To finish our exploration, let’s step off the Freedom Trail and visit a Boston legend of a different kind. While the city has enjoyed an impressive sports legacy through the years, none is as storied as its baseball organization. We head next to iconic Fenway Park, where the Citgo Sign, Prudential Tower and Green Monster watch protectively over each game. Built in 1912, Fenway is the oldest standing ballpark in Major League history — but baseball isn’t the only reason people gather here. Fenway has played host to football games, boxing matches, soccer matches and hockey games over the years, as well as concerts, memorial masses, election speeches, wedding ceremonies and even an elephant welcome party. Many historic aspects of the park still remain to this day. The foul ball safety screen behind home plate was the first ever in Major League history. See the ladder attached to the Monster? Suspended thirteen feet above the field, it was originally designed to allow the groundskeeper to retrieve balls hit into the netting, which was removed in 2003 and replaced with seats. The manual scoreboard in left field was installed in 1934 and is still used today; the few people allowed behind the scoreboard can see autographs from ballplayers who appeared in left field over the years. Read more about Fenway Park’s colorful history here.

Road Scholar Recommends:
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Relive the Revolution! Boston With Your Grandchild →

About the Author
JoAnn Bell, Senior Vice President, Program Development and Strategy, develops and manages more than 5,500 learning adventures in 150 countries and 50 states. JoAnn’s extensive travel industry experience informs her expert insight on everything from where to find the world’s most charming streets to must-see hidden gems across the globe.


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