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Berkshire Historical Society Executive Director Lesley Herzberg and Mayor Peter Marchetti unveil a sign recognizing the fatal accident that involved President Roosevelt in 1902.
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The new sign noting the event that injured Teddy Roosevelt and killed his Secret Service agent on their way to the Country Club of Pittsfield.
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Members of the Herberg Middle School Civics Club attended.
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South Street Sign Marks 1902 Roosevelt Trolley Incident

By Brittany PolitoiBerkshires Staff
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Mayor Peter Marchetti says its fitting the city memorializes William Craig, the first Secret Service agent killed in the line of duty. 

PITTSFIELD, Mass. — A sign now commemorates the location of an incident that made President Teddy Roosevelt say, "If you're set on risking your life, go to Pittsfield, Mass., and take a trolley ride."

The Berkshire County Historical Society last week unveiled a new historical marker near the corner of South Street and Mountain Drive that commemorates the trolley accident which killed Secret Service Officer William Craig and injured Theodore Roosevelt.

"We are here today because on September 3, 1902, President Theodore Roosevelt was visiting Pittsfield as part of a barnstorming tour through New England in support of local Republican candidates. Roosevelt was traveling in an open landau carriage from the center of the city to its outskirts along South Street. His destination was the Country Club of Pittsfield, where he was scheduled to sign the club's register before heading on to Lenox to deliver a speech," society Executive Director Lesley Herzberg said to a small crowd at the Country Club of Pittsfield.

Trolleys were supposed to be off duty that day, but one got a late start and, while attempting to arrive before the presidential party, crashed into Roosevelt's landau with deadly results.

"Agent Craig became aware of the approaching danger and stood, attempting to protect the president. He was thrown directly into the path of the trolley and was crushed under its wheels," Herzberg explained.

"… Roosevelt injured his leg, which he ignored at the time, more concerned with losing Craig. However, this injury plagued him and would require surgery at an Indianapolis hospital later that month."

The marker took five years of collaboration between the Historical Society, the city, the William Pomeroy Foundation, the Theodore Roosevelt Association, local historian Dr. Richard Henneberry, and the Herberg Middle School Civics Club.

It was funded by the William Pomeroy Foundation.

"This incident marked the first time in American history that a Secret Service agent was killed in the line of duty," Marchetti said.

"As we just recently celebrated Memorial Day, honoring men and women who made the ultimate sacrifice to our nation through their service in our armed forces, it is also fitting that we are here also taking this moment to remember the sacrifice of Agent Craig. Agent Craig, who diligently served both President McKinley and President Roosevelt, should always be remembered for his sacrifice to the country and the sacrifice for the nation."

When speaking about the agent, Roosevelt is quoted as saying, "The man who was killed was one of whom I was fond of and whom I greatly prized for his loyalty and faithfulness."

Secret Service member, who wished not to be named, said he appreciated the effort, and that "It means a lot to us." He had learned a lot he didn't know about Agent Craig in the last few weeks.

"All of us, when we go through our training academy, we do learn about those that were killed in the line of duty, but it's a fresh reminder for us, too, with things like this," he said.


William Craig, from the Officer Down Memorial Page. 
Craig was 48 years old and a native of Scotland. He had an adventurous life before immigrating to Chicago with his mother and sister. A former bodyguard to Queen Victoria, he served 12 years in the British army and was with the detachment that spent three years traveling to Khartoum in the failed attempt to rescue the ill-fated Major Gen. Charles Gordon. 
 
According to the Chicago Tribune, he was a physical director at the Armour Institute and the Yale-Princeton public school, where he gave exhibitions of his expert swordsmanship and boxing. He joined the Secret Service in 1900, working out of Alabama, where we helped bring down a gang of counterfeiters. He served in Pittsburgh and then joined the White House detail in 1901. He was to be married the next spring.
 
He is buried in Chicago's Oak Woods Cemetery. 

During the pandemic, BCHS was contacted by the Theodore Roosevelt Association asking if there was a marker on the site of the infamous trolley incident.

"When we realized there wasn't, we went on a journey to make this marker a reality," Herzberg explained.

After unveiling the sign, Historical Society members, city officials, and former Herberg students, who helped secure a grant and contributed to the research on the incident, gathered at the Country Club of Pittsfield.



Henneberry's daughter, Ellen Henneberry, explained that her Pittsfield native father is not a local historian but a neurobiologist. He currently resides in the state of Florida.

"This was a passion project of his, and he worked with a local city engineer on the research," she said. "I'm so happy that I could be here."

The 1902 trolley accident:
 
On Sept. 3, 1902, President Theodore Roosevelt was visiting Pittsfield, as part of a barnstorming tour through New England in support of local Republican candidates. Roosevelt was traveling in an open landau carriage from the center of the city to its outskirts along South Street. His destination was the Country Club of Pittsfield, where he was scheduled to sign the club's register before heading on to Lenox to deliver a speech. The driver and owner of the carriage, David J. Pratt was sitting on the raised front bench with Agent Craig. Inside the carriage were President Roosevelt, Massachusetts Governor Winthrop Crane, and Roosevelt's secretary George Cortelyou.
 
The carriage had made the descent from the center of town and was crossing the culvert over Wampenum Brook to start ascending "Howard Hill" (as it was locally known). The road narrowed at this point and carriages were forced to cross the trolley tracks, moving from the east to the west side of the street.
 
Trolleys were supposed to be off duty that day, per orders from the Secret Service. Inexplicably, trolley Number 29 was utilized by the owners and guests of the Pittsfield Electric Street Railway to the County Club. The trolley riders aboard Number 29 got a late start and wanted to arrive at their destination before the presidential party. The owners may have urged trolley driver Euclid Madden to speed up — he would later state that he thought that he would use the momentum built up going downhill to speed past the president's carriage.
 
Unfortunately, this did not happen. As the carriage crossed the trolley tracks, the two conveyances collided, with deadly results.
 
Agent Craig had become aware of the approaching danger and stood, attempting to protect the president. He was thrown directly into the path of the trolley and was crushed under its wheels. David Pratt also received serious injuries. The passengers were all thrown out of the carriage and injured, though none of these were life-threatening.
 
Roosevelt injured his leg, which he ignored at the time, more concerned with losing Craig. However, this injury plagued him and would require surgery at an Indianapolis hospital later that month.
 
He told an audience sometime later, "If you're set on risking your life, go to Pittsfield, Mass., and take a trolley ride."


Tags: historical event,   historical marker,   memorial,   secret service,   

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Friday Front Porch Feature: A Luxurious Home for Hosting

By Breanna SteeleiBerkshires Staff

DALTON, Mass. — Are you looking for a luxurious home with tons of amenities? Then this might be the home for you.

Our Friday Front Porch is a weekly feature spotlighting attractive homes for sale in Berkshire County. This week, we are showcasing 65 Johnson Road.

This 1998 single-family is newly remodeled and has four bedrooms and four bathrooms. It is 4,298 square feet on more than an acre.

It is on the market for $1,075,000.

The home includes a two-car basement garage, a home gym with equipment, and a custom mudroom. There is also a salt water pool and outdoor fire pit. The kitchen has custom built-in freezer and refrigerator, perfect for hosting, and comes with countless built-in space and custom drawers, including a built-in Miele coffee machine.

We spoke with Mia and Melissa Mazzeo with Berkshire Hathaway Homeservices Barnbrook Realty, which has the listing.

What do you think makes this property stand out in the current market?

Mazzeos: What truly sets this property apart in today's market is the exceptional quality and thoughtful attention to detail throughout. The sellers didn't just update this home — they reimagined it with care, intention, and craftsmanship. Every improvement was carefully considered, creating a move-in-ready space that feels both elevated and effortlessly livable

What was your first impression when you walked into the home?

It was an instant 'wow' moment. We were immediately impressed — and we absolutely loved the open floor plan. The space feels bright, connected, and perfect for both everyday living and entertaining.

Are there any standout design features or recent renovations?

Yes — this home truly has it all. Since 2018, the property has been fully renovated with both luxury and long-term quality in mind. Major improvements include a new roof, new windows, updated electrical and plumbing systems, new mini-split systems for efficient heating and cooling, new vinyl siding, and Trex decking for low-maintenance outdoor living. The pool has been converted to salt water, and the professionally updated landscaping enhances the home's curb appeal and outdoor enjoyment.

Inside, the level of customization is exceptional. Every detail was thoughtfully designed with built-in space for everything — including a dedicated coffee station, double dishwashers, a pullout shelf for your stand mixer, and custom drawers for cooking utensils. The large Sub-Zero refrigerator blends seamlessly into the cabinetry for a clean, sophisticated look. The dining room features a stunning built-in buffet complete with pullout refrigerator and freezer drawers, perfectly balancing elegance and functionality.

What kind of buyer do you see this home being perfect for?

This home is incredibly versatile. It's perfect for the buyer who loves to host and entertain, but just as ideal for a family seeking space and thoughtful design. And for someone who simply wants a private, peaceful setting to come home to — this property delivers that balance beautifully.

What would you say to a buyer trying to imagine their life in this space?

Close your eyes and imagine your dream home — every update completed, every amenity thoughtfully added, nothing left to do. Picture yourself soaking in the beauty of Berkshire County's ever-changing seasons through the windows of your all-season sunroom. Imagine the laughs and smiles that fill the air as you host loved ones in your chef's kitchen, designed perfectly for gathering and entertaining.

Now open your eyes… and you'll see 65 Johnson Road — the true definition of move-in ready.

You can find out more about this home on its listing here.

*Front Porch Feature brings you an exclusive to some of the houses listed on our real estate page every week. Here we take a bit of a deeper dive into a certain house for sale and ask questions so you don't have to.

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