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From the Bay Path to what we know today as our Boston Road, Route 20

Before we get into the history of the Bay Path, we would need to know a little background of this area we call the Connecticut River Valley. The settlement of Agawam Plantation later referred to as the Springfield settlement was established before the Bay Path, the northern route, was used by the Colonists to traverse back and forth from the Massachusetts Bay Colony to the Springfield settlement. This path was created after the Springfield settlement was established, most likely in the early 1640s. A survey map of this path was done in 1642 by Nathaniel Woodward and Solomon Saffery.


The second Europeans, the English, settlers came by ship sailing around Cape Cod and up the great river (Connecticut River). Prior to the English, the Dutch settled in Hartford Connecticut, and called this newly discovered river the Versche, meaning fresh water, but the Native Americans who occupied this area called it the Quinnehtuqut, meaning the long tidal river. The Native American designation survived, with a somewhat different spelling, first as the name of the river and later as the name of one of the four states it traverses.


The very first settlers of the Connecticut River Valley were Native Americans. These tribes consisted of the Agawam, Woronock, Podunk, Nonatuck, Wangunck, Tunxis, Nipmuc, and Pocumtuck to name a few. Some of these people have made this land their home for over 5,000 years. These Native Americans settling in the area now called Wilbraham operated two steatites (soapstone) quarries on Wilbraham Mountain, Glendale Road Area. Their finished products included implements of necessity and convenience. Soapstone artifacts include arrowheads, bowls, scrapers, awls, pipes, spear points, plow heads, hoes, hand hammers, digging tools, pestles, and cutting tools. Many of these early artifacts are on display at the Quadrangle Museums in Springfield and others are here at the Old Meeting House Museum.


Back in the early days, the landscape was much different. People would think of it as being a great forest with thick underbrush. But the exact opposite, with the land, lay open and passable in nearly every direction. The Native Americans would burn the land every year to bring in the grass and berry bushes, to attract the deer. The only dense forest of those days was in swampy areas where the fire did not reach.


So two theories about the travel of these early people, the first being, that Native Americans roamed at will, neither making heavily marked pathways nor needing them. The second theory is that Native Americans used footpaths, established by long use, to move between settlements and seasonal camps. Paths lead between spring sites for gathering plants and fishing and summer cornfields. These narrow paths were not always the straightest link between two places. The early people created the paths for ease and convenience, avoiding steep hills and crossing streams at shallow fords. I believe there is merit to both of these theories as we talk about this area in question.


The first Europeans, the Dutch, arrived in what is now Connecticut around 1614. Developing trade relations among indigenous groups. Despite being offered incentives to establish a presence in the river valley, the English initially expressed little interest until September 26, 1633, when a group of Plymouth settlers under William Holmes sailed up the Connecticut River. This group passed the Dutch fort located at modern-day Hartford and established a trading post of their own, just south of where the Farmington and Connecticut Rivers came together. The Connecticut River’s importance as a trade route continued to increase, with English settlers moving further up the river into Massachusetts and then beyond into New Hampshire and Vermont in search of pelts and other marketable goods.


William Pynchon sailed up the Connecticut River in 1635. Pynchon, Treasurer of the Massachusetts Bay Company and an experienced fur trader and businessman was searching for an ideal place to find a trading post and establish a Puritan "plantation". After quietly sailing past the Plymouth settlers, he reached the confluence of the Agawam and Connecticut Rivers.


William Pynchon in 1657

To Pynchon, it appeared to be the ideal place for his economic and religious venture into the wilderness. It was above the Enfield Falls and thus safe from enemy warships. It provided water access to the Berkshires and the greatly desired beaver. There was enough meadowland to support farms and cattle. After a tentative agreement with the local semi-nomadic Agawam Indians for the purchase of some of their land on the west side of the Connecticut River, Pynchon returned to the Boston area to recruit settlers. When he returned with settlers from Roxbury in the spring of 1636, he found some angry Indians. The cattle left behind in 1635 had trampled the Indian corn crop, and Pynchon was forced to establish his plantation on the east side of the river. On a large island in the river, Pynchon established Agawam Plantation as a fur trading outpost. He chose the site for its proximity to the indigenous groups from whom he could acquire beaver pelts and for the natural defense against attack provided by the river.


Pynchon envisioned the settlement as a self-sufficient industrial community, with agriculture necessary only for sustenance. The whole enterprise was initially based on the fur trade, and when the settlement expanded onto the less-fertile eastern shore of the river all but a few of the original settlers abandoned the island. Pynchon used land grants and indentured servants to populate the east side of the river, favoring admittance for those who could provide something of value to the community. He recruited artisans and tradesmen from other towns — carpenters, brick masons, smiths and coopers, weavers, and tailors — to make the settlement independent of outside sources of supply. In tribute to Pynchon's efforts on behalf of the village, settlers renamed it Springfield in 1640 after his hometown in England. Pynchon served as the Justice of the Peace and held court in his home. A board of selectmen governed the settlement.


It was about this same period that a more direct inland route was needed to travel from the Springfield Settlement to the Massachusetts Bay Settlement. In 1630, the Connecticut Path which led west along the north bank of the Charles River from New Town (Cambridge MA) to newly settled Watertown and passed through what is now Waltham and Weston, curving southward where it entered the southeasterly section of the new town of Sudbury, now set apart as Wayland.


In Wayland, around the early 1640s the Bay Path, the northern route, diverged from the Connecticut Path and headed west through Marlborough to Springfield and of course, passed through the north section of the Outward Commons (Wilbraham).


The Connecticut Path continued southward into Connecticut then in a westerly direction toward a small corner of Manchester before ending at the Connecticut River and then across into Hartford. These trails were being used frequently at this point taking a more southerly route to Connecticut and then up the river to Massachusetts.


What is now called the Old Connecticut Path and the Bay Path were used by John Winthrop to travel from Boston to Springfield in November 1645.


The colonists first used this trail to deliver the mail using post riders. The first ride to lay out the Bay Road (1647-1731) started on January 1, 1673. Later, the newly blazed trail was widened and smoothed to the point where horse-drawn wagons or stagecoaches could use the road. The country's first successful long-distance stagecoach service was launched by Levi Pease and Reuben Sikes along the County road (1731-1796) in October 1783. Rufus Stebbins, the author of the first Wilbraham history book, published in1863, claims Reuben Sikes, Pease's business partner, was a resident of Wilbraham and maintained a tavern for several years on the County Road. This tavern was located where 40 Maple Street is today. This information seems very probable, but could not be corroborated by any other source but we do know that Sikes Tavern did exist at that location.


In about 1675, the people of Springfield turned their attention to the hilly area to the east of the Springfield settlement and called it the “Outward Commons” or "Springfield Mountain." Some ten years later, they divided the land among the "landed proprietors" of Springfield but regarded it as common wilderness until 1731 when Nathaniel Hitchcock and his family came to settle on the West Road, our present Main Street, south of the center village. As the Outward Commons grew in population so did this important road for travel for these early residents, now known as the County Road (1731-1796).


The very first road, the old Bay Path, approximately the early 1640s, was laid out, Boston to the east and Springfield to the west, in the Outward Commons came other roads that branched from this road. The Town of Springfield laid out these new roads in the 1740s and traveled south to its southern boundary at the Connecticut line. They were the West Road (Main Street in Wilbraham, Wilbraham Road in Hampden, Somers Road in Hampden), the Middle Road (Mountain Road in Wilbraham, Ridge Road in Wilbraham, Peak Road in Wilbraham, North Road in Hampden, South Road in Hampden), and the East or Third Road ( Crane Hill Road in Wilbraham, Glendale Road in Wilbraham and Hampden, Monson Road in Hampden, Cross Road in Hampden, Scantic Road in Hampden). The next road to follow was sometime later, West Street as it was known later on (Stony Hill Road in Wilbraham and Hampden). At this point, there were soon to be inter-connected crossroads that would run east and west, just as the Bay Path did. When the first Meeting House was finished in 1748, many roads led to this area on Wigwam Hill.


In 1732, the County Road deviated from the original Bay Path that had traveled through this section of town since the early 1640s. At the point easterly of the Spear Brook hilltop, on what is Mountain Road today, the road was discontinued and the new road was laid more northeasterly for a short distance then travels east which follows the current Boston Road in Town. This new section of road that traveled downhill for a short distance before connecting to the current Boston Road had a very steep grade and was rocky. General George Washington even commented while traveling this part of the road on June 30, 1775, on his way to Cambridge to take command of the Colonial army, about its poor conditions. He also traveled this road again on October 22, 1789, when, as the first president of our country, he traveled to Boston. In his diary on this occasion, he recorded that the road in this place was rough and rocky, and went on to rest proximally 1.9 miles east of the Wilbraham-Palmer town line where today a memorial tablet is placed marking his resting point. The map below indicates that portion, marked by a blue/brown dotted line, of the road that Washington made an entry in his diary about the conditions of that road. In addition, one can still see the old stone bridge today that crosses Spear Brook, on that section of the old road. Please click the link for further information. https://david-bourcier.wixsite.com/wilbraham-tidbits/post/the-old-stone-bridge


Bay Path (black line) 1640s, Bay Path (black/white line) 1640s-1732, Bay Road (blue line) 1732, Bay Road (blue/brown line) 1732-1798, Massachusetts Turnpike (yellow line) 1798, and Boston Post Road (red line) 1852d
Boston Post Road in the early 1900s (Dugway 1798)

Other notable travelers on this road were British General Burgoyne and his army, who was escorted over this road on the way to Cambridge in late October of 1777, and his army was again escorted over it on November 18, 1778, on the way to Charlottesville, Virginia, where the climate was milder and food more plentiful, and the British became prisoners of war. On January 24, 1786, Revolutionary War veteran Daniel Shays reached Wilbraham by this road and spent the night with his soldiers quartered at Noah Warriner’s Tavern located on West Road (599 Main Street). On the next day, he would lead an armed rebellion in Springfield, Massachusetts to protest what he perceived as the unjust economic policies and political corruption of the Massachusetts state legislature.


Other significant changes to the old Bay Path took place in 1796 when the first Massachusetts Turnpike was chartered to improve the County Road from Warren to Palmer, then Wilbraham in 1798. The major change to affect Wilbraham was the construction of the "Dugway", the name given to the half-mile of heavy excavation along the Chicopee River bank. This Turnpike, as a corporate venture, lapsed around 1847. The toll house was at the foot of Butler Hill, just west of today's Crane Hill Road. Interestingly, there was a bypath circumventing the toll house, which destitute travelers sometimes used as a "shunpike." This bypass was located off of what is Three Rivers Road today in the area across from Circle Drive and headed southwest to the County Road just west of the toll house.


1892 photograph of the "Dugway" looking west. On the left, the stone retaining wall for the railroad which can be seen today.
1892 photograph of the "Butler Hill" looking west, area of Lebel Avenue.

Sometime after 1794, most probable in 1798 when the Turnpike authority was making improvements to the County Road, a section of today's Old Boston Road across from River Road was changed to a southwesterly direction to cross over Stony Hill Road and onto Dumaine Street and then connecting with Boston Road for the new and improved road.


Various changes with the Boston Post Road took place from 1837 to 1852 when in 1839 the Western Railroad was completed and the first train ran from Worcester to Springfield. These changes were a result of avoiding conflict with the new railway as it intersected with the road. Many of these changes resulted in railroad grade crossings being converted to railroad bridge crossings.


Bay Path (black line) 1640s, Massachusetts Turnpike (yellow line) 1798, and Boston Road (green line) 1895

In 1896, the last major change was made to reflect what Boston Road looks like today in town. A new road was constructed to avoid going over Moran's bridge onto today's Old Boston Road. The new road would stay south of the railroad and travel west until it eventually crossed Stony Hill Road and connected with the road that was constructed in 1798. Other minor changes also occurred over the various periods, again, mostly with the construction of the new railroad in the early to mid-1800s. The old Bay Path in Wilbraham has come a long way from an early crude path during the plantation period to the present day. It has been known by different names over the years such as the Bay Path, the Bay Road, the Country or Colony Road, the County Road, the Turnpike, the Post Road, and the Boston Road as we know it today.


Boston Road in Wilbraham is part of U.S. Highway 20. It is an east-west route that stretches from the Pacific Northwest east to New England. It spans 3,365 miles, it is the longest road in the United States. The highway's eastern terminus is in Boston, Massachusetts, at Kenmore Square, where it meets Route 2. Its western terminus is in Newport, Oregon, at an intersection with US 101, within a mile of the Pacific Ocean.


For great food and drink, please visit our friends, Frankie and Laurie at the Route 20 Bar and Grille. The restaurant is named after the famous Route 20 and is located on the original section of the 1640 Bay Path. Enjoy!!











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