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Letters Through Wilbraham: Tracing the Pioneering Postal Routes

The Boston Post Road, also known as the Upper Post Road, stands as the pioneering postal route linking Boston and New York, traversing through Wilbraham. It represents a significant historical artery alongside two other notable routes: the Lower Post Road and the Middle Post Road. Over time, segments of these pivotal postal roads evolved into prominent trails and pathways, laying the groundwork for several U.S. and interstate routes.


The Upper Post Road, the eldest among the designated trio, boasted the highest traffic volume. Its path roughly aligns with present-day U.S. Route 5 and U.S. Route 20. Conversely, the Lower Post Road hugs the coastline from New York before veering north through Providence, Rhode Island, en route to Boston. Portions of the Lower Post Road roughly correspond to the original alignment of U.S. Route 1 across eastern Connecticut, Rhode Island, and Massachusetts. Meanwhile, the Middle Post Road, the most direct and expedient route from New York to Boston, emerges as the youngest segment of the designated postal routes. Its trajectory loosely mirrors that of today’s U.S. Route 44 and U.S. Route 16. Interestingly, this route marked the inaugural trail, the Connecticut Path, where pioneering settlers from Boston ventured inland, drawn by the allure of the majestic Connecticut River Valley. It was along this path that they forged their way to establish the first vibrant settlements now recognized as Hartford, Windsor, and Wethersfield, Connecticut



Preceding the arrival of European settlers in North America, Native Americans forged trails that saw frequent use, eventually integrating into segments of post roads essential for mail delivery to early colonists. The inception of the Boston Post Road dates back to 1673 when the first sections were laid out, marking America's inaugural mail route. Throughout the 1700s, intrepid riders traversed the Boston Post Road, carrying the Boston News Letter, heralded as America's inaugural regular newspaper, alongside routine mail deliveries. This facilitated the dissemination of information among settlers and fostered the interconnection of towns dotting the route.


In 1753, Elliot Benger, the postmaster general for the colonies, retired from his position, paving the way for Benjamin Franklin and William Hunter to assume the mantle of responsibility. While ostensibly sharing the role of postmaster general, in reality, Benjamin Franklin emerged as the driving force behind the management of the colonial postal system, which operated under the auspices of the British government. Franklin's ambitious vision and proactive approach propelled him into a leadership position, guiding the direction and operations of the postal service during this pivotal period in colonial history.


Facing his initial challenge, Benjamin Franklin embarked on a crucial journey in the summer of 1753, a decade before Wilbraham's incorporation as a town. His mission: was to dispel the suspicions of his Yankee customers, who harbored doubts about the fairness of postage fees assessed by the mile. To tackle this issue head-on, Franklin embarked on a remarkable five-month expedition, meticulously surveying the postal roads utilized for mail delivery, including the original Upper Post Road that traversed the area now known as Wilbraham.


To ensure the most efficient routes for mail delivery, Franklin ingeniously devised an odometer, a groundbreaking invention for its time. This device, attached to his wagon, precisely measured the distance traveled by counting the revolutions of the wheels. Throughout his journey spanning approximately 1,600 miles of postal roads, Franklin's odometer meticulously recorded the distance covered along each route. To mark each mile, stakes were driven into the ground, while a dedicated crew followed behind, erecting durable stone markers along the surveyed paths.


Franklin's exhaustive efforts not only provided concrete evidence of the actual distances traveled along postal routes but also helped instill confidence among customers regarding the fairness of postage assessments. His innovative approach to surveying and his commitment to transparency laid a solid foundation for the efficient operation of the colonial postal system, ensuring reliable mail delivery and fostering trust among the communities it served.


In recent years, there has been controversy surrounding the claim that Benjamin Franklin personally laid out or ordered the placement of roadside milestones. Some argue that Post Office officials, including Franklin, had neither the responsibility nor the budget to build and maintain roads, bridges, ferries, or milestones. As a result, the exact truth of Franklin's involvement remains uncertain, and we may never fully uncover the facts."


On October 20, 1783, a pivotal moment in transportation history unfolded as the Boston Post Road, also referred to as the Upper Post Road, facilitated America's inaugural long-distance stagecoach and mail service connecting New York and Boston. This milestone marked a significant leap forward in the efficiency and accessibility of transportation across the young nation.


At the forefront of this transformative endeavor stood Levi Pease, a remarkable figure hailing from Connecticut. A skilled blacksmith, tavern owner, and distinguished war veteran, Pease played a crucial role in various specialized functions during the Revolutionary War. His responsibilities encompassed transportation-related tasks, including the delivery of correspondence, procurement of horses, and procurement of provisions for the army. Pease's unwavering dedication and resourcefulness significantly contributed to the logistical success of the military operations during this tumultuous period.


However, Pease's contributions did not end with the cessation of hostilities. In the subsequent years, he leveraged his expertise and experience to revolutionize mail delivery services throughout the United States. Pease's visionary initiatives and innovative spirit laid the groundwork for advancements in the transportation industry that resonated well into the 20th century.


Following the Revolutionary War, Levi Pease capitalized on his intimate knowledge of transportation routes and the New England region by embarking on a new venture. In 1783, he launched his first transportation route, linking Somers and Hartford, Connecticut, leveraging his expertise to establish a reliable connection between these two pivotal locations.


Recognizing the potential for expansion and eager to further enhance transportation and mail delivery services, Pease set his sights on a grander ambition: establishing a route spanning from Boston to New York City. However, such an endeavor necessitated both financial backing and a capable business partner.


In his search for a suitable collaborator, Pease turned to his trusted friend, Reuben Sykes, whose credentials as a blacksmith and tavern owner made him an ideal candidate for the partnership. Sykes, born in Springfield, Massachusetts, operated a tavern situated along the Boston Post Road, located at what is now 40 Maple Street in Wilbraham.  


The collaboration between Pease and Sykes marked the inception of a pioneering enterprise, with each man undertaking the arduous journey from their respective starting points—Hartford and Boston—at approximately the same time. This synchronized approach ensured the efficient and timely delivery of both passengers and mail between the two bustling cities.


Together, Pease and Sykes forged a pathway for improved connectivity and commerce along the bustling thoroughfare of the Boston Post Road, laying the groundwork for the expansion of transportation networks and the facilitation of vital communication across state lines. Their partnership exemplified the spirit of entrepreneurship and collaboration that characterized the early pioneers of America's burgeoning transportation industry.


Moreover, the reliability and efficiency demonstrated by the stagecoach and mail service on the Boston Post Road garnered the attention of Congress. Recognizing the potential benefits of utilizing stagecoaches for mail delivery, Congress made the momentous decision to transition from solitary riders to stagecoach transport for mail services. This shift not only expedited mail delivery but also contributed to the overall development of a more organized and dependable postal system across the nation.


In the autumn of 1789, following his inauguration as the first President of the United States, George Washington embarked on a historic tour along the famed Boston Post Road from New York to Boston. This journey through New England carried profound significance, symbolizing the new nation's unity and the President's commitment to forging strong ties with its diverse regions.


President Washington's tour commenced with his arrival in Springfield, Massachusetts, where he commenced his exploration of New England. His first official stop in Massachusetts was Springfield, where he inspected the federal arsenal, underscoring the importance of national defense and security.


Continuing his journey, President Washington's entourage traversed through various towns and villages along the Boston Post Road, including passing through Wilbraham on October 22nd and making notable stops in Palmer, West Brookfield, Brookfield, Spencer, Leicester, and Worcester. At each juncture, he was met with enthusiastic receptions and expressions of respect from the local populace.


One particularly memorable moment occurred upon his arrival in Worcester, where President Washington was greeted with a resounding 13-gun salute, a gesture of honor and reverence befitting his esteemed position.


Pressing onward, President Washington's itinerary carried him through Marlborough, Shrewsbury, Sudbury, and Weston before reaching his destination of Cambridge. Notably, Cambridge held special significance for President Washington, serving as his headquarters during the pivotal siege of Boston in the early stages of the Revolutionary War.


Upon his arrival in Cambridge, President Washington was greeted with great pomp and ceremony, as Lieutenant Governor Samuel Adams and the Executive Council welcomed him with utmost respect and honor. President Washington's diary reflects his appreciation for the warm reception, describing the occasion as "flattering & honorable" in every regard.


President Washington's journey along the Boston Post Road underscored his commitment to unity, reconciliation, and the cultivation of strong bonds between the federal government and the diverse regions of the fledgling nation. His historic tour left an indelible mark on the collective memory of the American people, symbolizing the promise of a united and prosperous future under the leadership of the nation's first President.


A charming anecdote from a letter penned by Antonette Catherine Mary Bliss (Speer) on December 30, 1878, reveals a delightful connection between her family and one of America's most iconic figures, General George Washington.


According to Antonette, her family's residence once served as a tavern along the Boston Road, situated alongside their property. This historic thoroughfare saw the passage of General Washington himself as he journeyed to and from Boston, undoubtedly on significant missions that shaped the course of American history.


Antonette's recollection vividly portrays the excitement and awe experienced by her father, John Bliss, and other young boys in the neighborhood. They would eagerly gather at the corner of the road, eagerly anticipating the sight of the esteemed General as he passed by. Their anticipation was met with immense gratification when General Washington, the "stately Chieftain," bestowed upon them a gesture of acknowledgment—a bow—as he rode past.


Today, as we reflect on the pioneering postal route and stage line that once traversed Wilbraham, we honor the trailblazers who paved the way for progress and prosperity in our nation's history. Their story serves as a reminder of the transformative potential of visionary ideas and collaborative endeavors, inspiring us to continue pushing the boundaries of innovation and connectivity in the pursuit of a brighter future.



Benjamin Franklin as Postmaster General. Philadelphia History Museum at the Atwater Kent, / Bridgeman Images.

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