Private Full Day Tours of Charlestown with L. Cobb
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Private Full Day Tours of Charlestown with L. Cobb 〰️
Charlestown- Boston Oldest Neighborhood 1628
Tours of Charlestown
Includes: Bunker Hill Monument, Charlestown Navy Yard, USS Cassin & USS Constitution and we include our MOVIE Tour!
John Harvard Mall / Site of John Harvard’s House: Tucked right next to City Square Park at the end of your route. Most people don’t realize that the founder of Harvard University actually lived right here in Charlestown. He died here in 1638, leaving his massive book library to the fledgling college across the river. It’s a gorgeous, hidden brick plaza that makes a great storytelling stop
St. Mary’s Church (Winthrop Street): Built in 1889, this is a massive piece of the neighborhood's traditional Irish-Catholic working-class identity. The soaring Romanesque architecture and incredible stained glass windows inside are a stunning visual stop if you are highlighting the cultural shift of the 19th century.
The Phipps Street Burying Ground: Dating back to the 1630s, this is one of the oldest cemeteries in the entire country, completely tucked away from the main tourist paths. It survived the burning of the town during the Battle of Bunker Hill and contains some of the earliest, most hauntingly beautiful slate gravestones in New England.
The Warren Tavern : Doctor Joseph Warren was one of the most influential patriots of the American Revolution. A Harvard-educated physician and surgeon practicing in Boston, Warren was also a Grand Master of the Freemasons, a member of the Sons of Liberty and part of the Boston Committee of Correspondence. He authored the Suffolk Resolves, which his close friend Paul Revere carried to the First Continental Congress where they were endorsed on September 17, 1774. Warren also famously dispatched Paul Revere and William Dawes on their midnight rides to Lexington on April 18, 1775.
Just days before the Battle of Bunker Hill, the Massachusetts Provincial Congress appointed Warren a Major General. Yet when Major General Israel Putnam and Colonel William Prescott offered him command during the battle, Warren declined, choosing instead to fight alongside the men as a volunteer with musket in hand.
As British forces launched their assault on Breed’s Hill, patriot sharpshooters positioned throughout Charlestown inflicted heavy casualties. In response, British ships fired incendiary shots and landing parties set fire to the largely wooden town. From Boston and beyond, colonists watched Charlestown burn. The British first attack on the American left flank failed and a second assault on the redoubt was also repelled. British losses mounted, including many officers. On the third assault, the British overtook the redoubt and Doctor Joseph Warren was killed in battle.
Today, the Bunker Hill Monument stands on the site of the original redoubt, honoring the patriots’ heroic stand on June 17, 1775. Inside the lodge at the base of the monument is a marble statue of Major General Joseph Warren. Just across the street, the Bunker Hill Museum tells the story of Charlestown, the battle and the monument itself.
A short walk away on Pleasant Street stands one of the first buildings rebuilt after the British burned Charlestown: The Warren Tavern. Constructed in 1780, the tavern has welcomed visitors for nearly 250 years, including George Washington in 1789 and Paul Revere.
Abraham Lincoln Post 11 / Memorial Hall
Located at 14 Green Street, this building is a fascinating "architectural hybrid." It began as the Samuel Dexter House in 1791, a grand Federal-style mansion. In 1888, it was transformed into the headquarters for the Grand Army of the Republic (GAR), an organization of Union Civil War veterans.
The "Raised" Roof: To create a second-story meeting hall, the original 1791 roof was actually jacked up over six feet, giving the building its unique height.
Continuous Service: It has served veterans for over 130 years and remains one of the oldest continuously active veterans' halls in the country.
Films:
The "Good Will Hunting" Classrooms (Bunker Hill Community College):
Right back at your starting point. While the movie famously highlights Harvard and MIT, the actual office where Sean (Robin Williams) first sits down with Will (Matt Damon) and challenges him was set right here at the community college.
"The Town" Heist Markers (Old Sully's / Monument Laundry): If you want to tap into Ben Affleck’s 2010 crime thriller The Town, you can point out where real neighborhood landmarks became movie sets. Monument Laundry (142 Bunker Hill St) is where Doug contrives his accidental meeting with Claire, and the exterior of the gang's local hangout, Old Sully's, sat right down near Union Street by the T stop.
The Charlestown Steps (Phipps Street Area): Featured prominently in the 90s action thriller Blown Away starring Jeff Bridges and Tommy Lee Jones. Locals use them for morning cardio, but on a tour, they showcase the steep, dramatic topography of the hill.
Schrafft's Chocolate
This company had a fascinating journey that transformed a small Boston confectionery into a global industrial giant and a cultural touchstone of 20th-century American life.
The Sweet Origins and Civil War Innovation
The business began in 1861 when Bavarian confectioner William F. Schrafft opened a small candy-making shop in Boston.
He focused on high-quality chocolates, hard candies, and gumdrops.
The Jelly Bean Pioneer: Schrafft’s is widely credited with popularizing the modern jelly bean in the United States. During the Civil War, William Schrafft aggressively marketed his new, durable round candies, encouraging citizens to buy them and mail them to Union soldiers on the front lines as a sweet, long-lasting morale booster.
The Shattuck Partnership: In the late 1890s, a brilliant traveling salesman named Frank G. Shattuck teamed up with Schrafft. While the Schrafft family focused on manufacturing the chocolate in Boston, the Shattucks opened elegant retail candy shops in New York to sell them.
The Massive Charlestown Factory
By the 1920s, demand was so massive that the company built the sprawling, 1.2 million-square-foot Art Deco factory at 529 Main Street in Charlestown, which opened in 1928.
The Candy Capital: At its peak, this single facility was the largest candy factory in the entire world, churning out millions of pounds of chocolates, jelly beans, and novelty sweets. It employed more than 1,600 workers—a major economic engine for Charlestown.
The "Welcome Home" Beacon: The iconic red neon sign and the massive clock tower were erected with the building in 1928, serving as a landmark for maritime traffic and later for millions of commuters traveling on Interstate 93.
Becoming a Lifestyle Brand
Genteel Dining: By the mid-20th century, there were over 50 elegant Schrafft's restaurants along the East Coast. They became legendary as safe, respectable, and sophisticated places for independent women to lunch, famous for their immaculate waitress uniforms, hot butterscotch sundaes, chicken à la king, and cream cheese sandwiches with the crusts cut off.
Pop Culture Icon: Schrafft's became a staple of American culture. The brand sponsored the very first annual CBS television broadcast of The Wizard of Oz in 1959. In 1968, trying to modernize its image, the company even commissioned pop artist Andy Warhol to create a psychedelic 60-second television commercial for their chocolate sundaes.
The Shift and Closure
As the 1950s and 60s progressed, consumer habits shifted dramatically. The entire confectionery industry underwent massive changes:
The Candy Bar Boom: Boxed chocolates—Schrafft’s specialty—were steadily squeezed off shelves by the massive rise of cheap, individual candy bars.
Distribution Issues: While competitors began selling directly to massive supermarket chains, Schrafft’s stuck to traditional distributors for too long, losing critical market share.
The candy and restaurant operations were split and sold to corporate conglomerates in the late 1960s. After years of struggling against changing tastes, the Charlestown factory finally closed its doors for good in 1984.
Today, while you can no longer buy a box of their famous thin mints or assorted chocolates, the legacy remains alive through the beautifully preserved The Schrafft Center office complex and the glowing neon sign that still lights up the Boston skyline every night.