The Oregon Trail

1907 map showing the main route of the Oregon Trail

As a child, I was fascinated by historical stories of explorers, adventurers and pioneers.  In particular, the Oregon Trail was a topic that I was especially obsessed with.  I have fond memories of playing the Oregon Trail video game as well as other Oregon Trail games and activities in school.

At the time, I had no idea that many of my ancestors had actually traveled on the Oregon Trail and had their own stories about their long journeys into the wilderness.  Specifically, 13 of direct ancestors traveled on the Oregon Trail in five different crossings between 1843 and 1852.  In total, at least 57 family members made the trip in the same 5 trips.  (All of these people were ancestors and relatives of my maternal grandfather Ben Plymale.) 

This blog post explores these Oregon Trail journeys and the stories that have survived about them.

Deaths

The majority of my family safely traveled the Oregon Trail and arrived to their destinations with little or no incident.  There were a few family members though who died during or as a result of their journeys:

• In about April 1852, my great-great-great-grandfather's first wife, Mary Lewis Merriman, died of an unknown illness somewhere in what is now Kansas - and was buried by the trail's side. 
• In about August 1852, my great-great-great-grandfather's infant son Joseph W. Merriman died in northern California after drinking cow milk that was contaminated by poisonous wild parsnips. He went into convulsions and died within hours.  He was buried by the trail's side. 
• In October 1852, my great-great-great-great-grandfather Gabriel Plymale and his son Anderville Plymale both contracted typhoid fever after drinking contaminated water at Goose Lake in northern California.  They died within two months of arriving in Oregon. 

Injuries

• Sometime in late summer 1851, while the train was somewhere in Nevada, my great-great-great-great-grandparents' 6-year old son John B. Riddle fell from a moving wagon and was run over by the front wheel but was pulled to safety before being run over by the rear wheel.  He was briefly unconscious, but made a full recovery. 

Other 

• In 1851, the wagon train that the Riddle family was traveling in was attacked by Indians and one of the men in the train was shot in the arm.  My great-great-great-grandmother Artinecia Riddle Chapman performed a minor surgical operation by removing bone fragments from the wound. 
• From 1843-1844, my great-great-great-grandfather William J. Martin went on an expedition to Oregon and California with the explorer John Fremont.  The reports created during the trip were said to be responsible for the Mormons choosing Utah as a place of settlement.
  

Artifacts

• There are two quilts from the Riddle family that they brought with them over the Oregon Trail in 1851.  There is also a "ginger jar" brought by the Plymale family in 1852.  These items are held by the Southern Oregon Historical Society in Medford, Oregon.

 Diaries/Stories

• Brief Review of the Life of Isaac Constant -  Transcription of an interview (c. 1890s) with Lavinia Constant Robinson who was 18 years old when she crossed the Oregon Trail in 1852 (Lavinia was the niece of my great-great-great-grandfather William Merriman)
• Early Days in Oregon - Series of articles written by George W. Riddle in 1920, recounting his family's journey on the Oregon Trail in 1851 and subsequent pioneer life (George was the brother of my great-great-great-grandmother Artinecia Merriman)
• The Unknown - Article written by William J. Plymale (date unknown) regarding an 1852 Oregon Trail journey (William Plymale was my great-great-grandfather)
  

1843 - Martin

My great-great-great-grandfather William Martin
of Missouri.  He went on an expedition to
Oregon and California in 1843.  He later moved to Oregon
with his family in 1846.
(courtesy Douglas County Museum)

In 1843, my great-great-great-grandfather William J. Martin was 28-years old and lived in western Missouri. He was married and had one young daughter.  He had worked as a farmer, tavern keeper and ferry boat operator and was also a wounded war veteran.  We can assume that he was restless with a drive for adventure.  For unknown reasons, he decided to leave his family and go on an exploratory expedition to the west coast.  It must have been especially difficult for his young wife Harriet, who was left alone with their child and the very real possibility that he might never return.

The spring that year was very late and so the departure of the train was delayed. The party finally left Missouri on May 22, 1843.  The train traveled west until June 8, 1843, when the captain - Peter Burnett - resigned.  William Martin was then elected captain in his place.  At that time, the wagon train split in two.  William Martin continued as captain of the smaller group - with 72 wagons and 175 men.  During his tenure as captain, William apparently had trouble controlling many of the younger men in the group.  (It was probably because of these problems that William declined serving as captain when he made the same trip 3 years later).

When the train reached the Rocky Mountains (probably in what is now Wyoming), William was remembered for killing an animal that was described as a "rare carnivorous animal, much like a hyena" (probably a wolverine).  Somewhere in Idaho, William joined with a group of men traveling to California.  At this point, it is not clear what route or schedule they took to get there - but they probably traveled through Idaho, eastern Oregon and northern California.  Eventually, William arrived at Sutter's Fort, California (in modern Sacramento) in early 1844.  William spent 6 weeks at Sutter's Fort.  Then in March 1844, William joined with the explorer John Fremont in an expedition back east.  (The city of Fremont, California and Seattle's Fremont neighborhood are both named after this explorer).  

The Fremont expedition left Sacramento in March 1844 and traveled south through the San Joaquin Valley of California.  At about what is now Bakersfield, California they turned east into Nevada and went through what is now Las Vegas.  From there, they traveled north through Utah and met up with the traditional Oregon Trail in Wyoming.  They then traveled east through Wyoming, Nebraska and Kansas.  They arrived back home in Missouri in August 1844 and William rejoined his family.  Some of the reports created on this expedition were said to be responsible for the Mormons choosing Utah as a place of settlement. 

References:

Bakken, Lavola J. "William Jennings Martin." The Umpqua Trapper, 13(4). Douglas County Historical Society, Roseburg, OR, 1977. 

Obituary of William Martin, The Plaindealer, Roseburg, OR, Apr. 29, 1901

1846 - Martin

Letter written by William Martin in 1846 advising other emigrants
on how to prepare for the Oregon Trail. 
Transcribed and published in Overland in 1846, Volume 2.

After visiting Oregon and California in 1843-1844, William J. Martin quickly realized that he wanted to move out west permanently.  In addition to deciding to move with his wife and children; he was able to convince many of his relatives to move as well.  In 1845, his brother and sister migrated over the Oregon Trail with their families.  The other members of the family (including William) decided to wait an additional year.  

William and his family were busy preparing for the move between 1845 and 1846.  In January 1846, William wrote a letter - which was published in the St. Joseph Gazette newspaper - advising other emigrants on how to prepare for the journey.  During the last months before departure, many of William's friends tried to convince him to be Captain of the wagon train.  He declined the offer though, because it entailed "much responsibility and little honor."  Although William initially declined serving as captain, he unofficially traveled in a leadership capacity and was called captain anyway.  His family's wagons were often in the lead of the wagon train.  

The Martin family that traveled in 1846 included about 17 members: William Martin (31), his wife Harriet Martin (29); their daughters Catherine (4), Frances (10 months) and Josephine (my great-great-grandmother - 10 months); his mother-in-law Catherine Crobarger (68); his parents Zadock Martin (57) and Susannah Martin (about 58); his brother Frank Martin (34) and sister-in-law Lucretia Martin (18).  The family also probably traveled with William's paternal cousin Franklin Martin (22) as well as his maternal cousin Milton Brown (31) and Milton's wife Christina Brown and their four children: Mary, Susan, James and Frances Brown. 

The family left their homes near Platte City, Missouri (near what is now Kansas City) in early April 1846.  We do not know much about this particular wagon train's crossing - it must have been relatively uneventful.  They apparently traveled north from their homes and left from St. Joseph, Missouri on about April 10, 1846.  Their wagon train was quite large, with over 100 wagons and 600 people.  Over the duration of the crossing - the train split off into different groups at least two times.  From St. Joseph, they traveled west through what is now Kansas, Nebraska, Wyoming, Idaho, and finally into Oregon.  They were at Fort Laramie, Wyoming on June 10, 1846.  On June 23, 1846, an observer came across the Martin wagon train when it was crossing the North Platte River, in central Wyoming, and made the following observation: "we had the pleasant sight of beholding the valy (sic) to a greate (sic) distance dotted with peopl (sic) horses cattle wagons and tents their being 30 wagons all buisily (sic) engaged in the crossing the river which was found to not be fordable with the poor material they had to make rafts of it took two trips to carry over one wagon with its lading." Another observer mentioned finding the Martin train at Red Butte, Wyoming and that they were "travelling (sic) on cheerily, having met with few impediments to their journey."

The train arrived in northern Oregon on September 15, 1846 and the family quickly moved to Yamhill County, Oregon (southwest of what is now Portland), where William's brother Hardin had settled the year before.  Eventually, the family dispersed and moved elsewhere.  My ancestor William Martin moved with his family to southern Oregon; where they remained.

References:

Morgan, Dale. Overland In 1846: Diaries and Letters of the California-Oregon Trail. Volume 1. Talisman Press, Georgetown, CA, 1963.

Morgan, Dale. Overland In 1846: Diaries and Letters of the California-Oregon Trail. Volume 2. Talisman Press, Georgetown, CA, 1963.

Genealogical Material in Oregon Donation Land Claims, Volume III.

Bakken, Lavola J. "William Jennings Martin." The Umpqua Trapper, 13(4). Douglas County Historical Society, Roseburg, OR, 1977. 

1851 - Riddle

My ancestors William and Maxamillia Riddle photographed at
about the time that they migrated over the Oregon Trail, in 1851
(courtesy Douglas County Museum)

In 1850, my great-great-great-great-grandparents, William H. Riddle and Maxamillia Bouseman Riddle, lived on a corn farm near Springfield, Illinois.  In the summer of 1850, one of their neighbors - Isaac Constant - returned from a trip to Oregon and began inspiring his neighbors to move out west.  He brought tales of fertile farming, mild climates and gold. 

The Riddle family quickly decided to sell their 200-acre farm and move out west on the Oregon Trail.  The family spent the winter of 1850-1851 preparing for their trip.  William and Maxamillia decided to make the trip with their 7 unmarried children (Isabella, William, George, Abner, John, Anna and Tobias), Maxamillia's half-sister (Lucinda McGill), and an orphaned niece (Ann Hall).  At the time, William and Maxamillia’s two eldest children (Jane and Artinecia) were already married.  Jane and her husband (Thomas Wilson) decided to remain in Illinois, but Artinecia and her husband (James Chapman) decided to make the trip.  Sadly, sometime in the early months of 1851 - while still in the planning stages – James Chapman died suddenly.  His 20-year old widow Artinecia Chapman (my great-great-great-grandmother) had to bury her dead husband and continue preparations to leave with her 1-year old son, John Chapman.  As she bluntly said in 1915: "There was nothing left for me to do but come along with my folks."   

Fortunately, the details of their journey have been written down for posterity.  In 1920, William and Maxamillia's son George Riddle (who was 11 years old at the time of the journey) wrote a series of articles about his family's journey on the trail and subsequent pioneer life in Oregon.  His articles were compiled and published in a book, Early Days in Oregon, which is available online.  

In about 1914, the Riddles' daughter Artinecia appeared in a silent movie.  She was filmed being interviewed about early pioneer life in Oregon.  The movie - Grace's Visit to the Rogue River Valley - was produced to promote southern Oregon at the Pan-Pacific Exposition in San Francisco in 1915. 

This quilt was made by Maxamillia Riddle and brought
over the Oregon Trail with her family in 1851.  The quilt
is currently in the Southern Oregon Historical Society
(photo courtesy Chris Meinicke)

After months of preparation, the family left their home near Springfield on about April 10, 1851.  The family's train included three wagons (one belonging to their daughter Artinecia), each drawn by six oxen; and one large carriage, drawn by four horses. From Springfield, they traveled directly west - going through Illinois before crossing into northern Missouri.  While traveling through Missouri, the family apparently had their first glimpse of slavery, which was legal there.  They then crossed over into what is now Iowa and reached Council Bluffs.  The train was then slightly delayed due to flooding on the Missouri River.  They then crossed into "Indian territory" and their first camp was in what is now Omaha, Nebraska.  When camped there, they were raided by Indians - who stole some of their cattle.  William Riddle rode after the Indians to retake the cattle, but could not find them.  Sadly, when William Riddle was fording across Papio Creek (near Omaha), his beloved horse named "Puss" fell in and drowned. 

From Omaha, the family traveled west along the Platte River, through what is now the state of Nebraska.  Then near what is now Columbus, Nebraska - they joined with another wagon train that was coming from Iowa. Most of their journey at this part of the trail seemed relatively uneventful.  As George Riddle put it, "Our greatest annoyances were mosquitoes and buffalo gnats."  When the wagon train was near Fort Laramie (in Wyoming), they passed a large group of Sioux Indians.  Instead of being hostile though, the Indians forbid the white travelers to approach because they were afraid of smallpox and other diseases they might have been carrying. 

On July 4, 1851, the wagon train reached Independence Rock, in central Wyoming.  Independence Rock was one of the best known landmarks on the Oregon Trail - and marked the halfway point.  Not long after this point, an unknown factor caused the oxen in their train to stampede, which resulted in one overturned wagon - but no injuries.  The train then crossed into Idaho and reached the fork of the California and Oregon Trails at Soda Springs.  The family had previously made the decision to take the California Trail and thus enter Oregon from the south.  The wagon train split in two and the train proceeding south on the California Trail (including the Riddles) only consisted of "twelve wagons and about twenty men" (and an unknown number of women and children). 

From Soda Springs, the train traveled southwest, through Idaho and into Nevada.  George Riddle mentioned that they traveled within one hundred miles of the Mormon settlement of Salt Lake City, but that they encountered no Mormons on their journey.  From this point though, they apparently had frequent interactions with the local Indians.  At one point, there was an armed confrontation in which shots were fired from both sides, but no one was injured (except for a woman who fell from her horse). 

Clip from the 1915 silent movie "Grace's Visit to the Rogue River Valley"
featuring my great-great-great-grandmother
Artinecia Merriman being interviewed about pioneer life

The next incident during the trip was when they were near the Humboldt River at what is now Winnemucca in northern Nevada.  At that time, there was an armed confrontation between the local Indians and one man (John Welch) who was driving the wagon that was then in the lead of the train.  His wagon was fired on by the Indians and John Welch was shot in the arm and resulting in shattered bones.  Since there was nobody in the wagon train that had any surgical or medical skill, my great-great-great-grandmother Artinecia Chapman (then aged 20) was called on to perform a basic operation and dress the wound (she had to feel for and extract shattered bones from the wound).  According to George Riddle, "I witnessed the operation and it made such an impression on my mind that at times I can visualize the operation. My sister Artinecia, was a brave girl." The man made a full recovery.

Another incident also occurred in northern Nevada.  While the train was moving, William and Maxamillia’s son John Riddle (aged 6) fell from the moving wagon and was run over by the front wheel, but was pulled to safety before the rear wheel hit him.  He was unconscious for some time, but made a full recovery. 

The simple log house that the Riddle family built in Douglas County, Oregon in
1852, soon after arriving on the Oregon Trail
(Courtesy Southern Oregon Historical Society)

Then at Black Rock Desert, in northwest Nevada, they turned off the California Trail and onto the Applegate Trail - which would take them north into Oregon.  From there, the route was especially treacherous as they traveled in many miles of desert, with no water.  There, they were able to witness the evidence of previous wagon train crossings in which animals died or they had to abandon items. "We were seldom out of the sight of the carcasses of dead cattle" and "all along the road were abandoned wagons, household goods of every description.  Here would be a cook stove, further on a plow, then the remains of a feather bed."  The following year, the wagon train containing the Merriman and Constant families (described below) claimed to have found an abandoned wagon in this area belonging to a Mr. Riddle.  The Riddle family did describe abandoning their carriage - but that was along the Platte River (in Nebraska or Wyoming) - and not in Nevada. 

When the party was still in Nevada, they uncovered two abandoned fifty gallon barrels - one filled with whiskey and the other with brandy.  The emigrants made the decision to take the alcohol with them.  The train then arrived in northern California and made its way north.  At Tule Lake, they had a nonviolent confrontation with the local Indians (the following year, a wagon train was massacred at this very location and it came to be known as "Bloody Point").  From there, they traveled into Oregon and continued to make their way north.  By this time, the family's food supplies were almost gone, but they were fortunate to come across pack trains who sold them some food. 

They arrived at Canyonville, Oregon on September 20, 1851.  Most of the wagon train continued on to northern Oregon, but the Riddles decided to stay there.  They went nearby to the Cow Creek Valley and claimed a 320-acre farm there. They are credited as being the first white settlers of in the Cow Creek Valley. At that time, the Riddle family were among a very small group of white settlers in all of southern Oregon.  Apparently, their nearest neighbor was 8 miles away and there were only 3 other houses in 25 square miles.  Apparently, my great-great-great-grandmother Artinecia (then 20) and her sister Isabella (then 18) were not happy about this.  According to George "This seemed out of the world to my two older sisters and I remember there were tears and wailings that we have left Illinois and endured all of the hardships of the plains to settle down in a place where they would never see anyone and never have any neighbors." 

The small city of Riddle, Oregon (platted by their son John in the 1880s) was named after their family.    

References:

Riddle, George W. Early Days in Oregon. South Umpqua Historical Society, Canyonville, OR, 1993 (written in 1920).

Transcript of interview with Artinecia Merriman, Oregon Journal, Sep. 19, 1915.
Genealogical Material in Oregon Donation Land Claims, Volume III.

1852 - Merriman

William Merriman crossed the Oregon Trail
in 1852, but his wife and son both died during
the journey
(courtesy Douglas County Museum)

In 1852, my great-great-great-grandfather William H. Merriman was a 27-year old carpenter who lived with his wife and two children near Springfield, in central Illinois.  In 1850, William’s brother-in-law Isaac Constant returned to Illinois from a trip he had taken to Oregon.  He began telling his neighbors and relatives about the charms of the Oregon Territory and began inspiring them to move out west.  One family that he convinced to pack up and move was that of his brother-in-law, William Merriman.

William and his family - which included his wife Mary and their two small children, Auletta (3) and Joseph (infant) - decided to make the trip.  Also coming was Isaac Constant, his wife Lucinda Merriman Constant, and their 6 children: Lavinia, Thomas, Elizabeth, Julia, Margery and Alice.  All of the other Merriman family relatives (including 5 siblings of William and Lucinda and many nieces, nephews and cousins) decided to remain in Illinois.
Luckily, we have many details of this particular Oregon Trail journey.  Many years later (during the 1890s), the details of the crossing were written down by Thomas Robinson who interviewed his mother Lavinia Constant Robinson (William Merriman's niece, who was 18 at the time of the journey) about her experiences on the trail.  Lavinia's story, A Brief Review of the Life of Isaac Constant, can be read online.

The family left Springfield on March 2, 1852.  From there, they traveled by wagon to St. Louis, Missouri, where they spent a few days with a relative who lived there.  They then boarded a boat and traveled on the Missouri River from St. Louis to Independence (near what is now Kansas City).  The group then spent a few weeks in Independence, preparing for the wagon train.  During this time, Isaac Constant was elected Captain of the wagon train.  The family left Independence in the early days of April 1852, and the train was off!

Sadly, William Merriman’s wife Mary was very sick with an unknown illness when the journey began.  She died at the first stop after leaving Independence, somewhere in what is now eastern Kansas.  They had to send back to Independence for a casket to bury her in.  She is probably buried somewhere by the trail’s side.  The situation must have been especially tragic for William.  His wife was now dead and he had two very young children.  His baby, Joseph, was so young that he was still nursing at the time of his mother’s death.  To keep the baby alive, William fed him milk from one of the cows in the train. 

The wagon train continued on the Oregon Trail; going through what is now Kansas, Nebraska, Wyoming and into Idaho.  Near Fort Hall, Idaho (near what is now Pocatello), the train split in two; one trail going west towards northern Oregon and one trail going southwest towards California and southern Oregon.  The Merrimans and Constants continued on the southern trail (also known as the California Trail).  From there, they traveled through Nevada and then took the Applegate Trail into northern California.  When the family stopped at Goose Lake (border between Oregon and California); the cow that was providing milk for William’s baby Joseph had eaten some wild parsnips (which are poisonous).  After drinking the milk, the baby sadly went into convulsions and died.  During the whole trip, the only deaths in their wagon train were William’s wife and son.  At some point during the trip, Indians attacked their train and stole two of their mules and ate them. 

The train then entered Oregon and arrived at its destination in what is now Jacksonville, Oregon on September 21, 1852.  William did not remain in Jacksonville for long.  He left his 3-year old daughter in the care of his sister Lucinda and proceeded about 80 miles north to what became Douglas County, Oregon.  There, he began to court a young widow named Artinecia Chapman (they had known each other when they lived in Illinois).   She had migrated from Illinois with her infant son, parents and siblings the previous year (see above).  They married in February 1853 and settled briefly near her parents in Douglas County, Oregon before moving permanently in Jackson County, Oregon in 1857. They had a large family - 15 children in addition to their 2 children from previous marriages.  Merriman Road between Medford and Central Point is named for their family.

Isaac Constant and his family settled on a land claim in the valley northeast of Jacksonville.  Eventually the town (and later city) of Central Point sprang up around their home - and they are considered by many to have been the founders of Central Point.

References:

"A Brief Review of the Life of Isaac Constant." Written by Thomas M. Robinson from an interview with his mother, Lavinia Constant Robinson, c. 1890s.

Obituary of Julia Owen, Central Point American, Jan. 9, 1936, Pg. 1
Genealogical Material in Oregon Donation Land Claims, Volume III.

1852 - Plymale

Sarah Plymale was 12 years old when she crossed
the Oregon Trail with her family.  Later, she and her
sisters were among the only eligible females in
Jacksonville, Oregon (there mostly being gold miners)
(courtesy Southern Oregon Historical Society)

In the late 1840s, my great-great-great-grandparents Gabriel Plymale and Polly Hatfield Plymale lived with their family near Galesburg, in northwest Illinois.  They were farmers and also involved in the lumber trade; requiring biannual trips to Chicago, Illinois.  In 1848 or 1849, Gabriel’s brother James Plymale left his home and went to California to mine for gold.  James was successful in locating gold in California; but was attacked and robbed on his way back east – resulting in the loss of all of his gold and apparently one of his arms.  Despite this, his experience had apparently given his brother Gabriel the desire for adventure and “gold fever”.  Eventually, Gabriel and Polly made the decision to abandon their life in Illinois and try their luck mining for gold on the west coast.  When gold was discovered in what is now Jacksonville in southern Oregon in late 1851, they quickly made the decision to move there.

The Plymales left their Illinois home in the spring of 1852.  Their party included 15 family members; 47-year old Gabriel and 48-year old Polly; their 9 unmarried children: Anderville  (21), Francis (19), Elizabeth (17), William (my great-great-grandfather - 15), Sebastian (13), Sarah (11), Narrissa (10), Mary (8), and Emma (4).  Also coming in the train was their eldest daughter Minerva  (22), her husband Robert Armstrong (25) and their two children: Marcus (3) and Mary (1). 

My great-great-great-grandmother Polly Plymale brought this
"ginger jar" with the family during their trip over the Oregon
Trail in 1852.  She gave it as a wedding gift in 1867
(courtesy Southern Oregon Historical Society)

We know little about this particular Oregon Trail migration – other than that they came by the California and Applegate Trails (which would have taken them through Illinois, Missouri, Kansas, Nebraska, Wyoming, Idaho, Nevada, northern California and finally into Oregon).  At one point in their journey, there was some kind of commotion which caused the oxen in the train to stampede.  The Plymales’ 1-year old granddaughter Mary Armstrong fell from the moving wagon but was saved from death by her mother who grabbed her leg and pulled her to safety.

Eventually, in the fall of 1852, they had reached northern California.  The train stopped at Goose Lake (on the border between California and Oregon), and Gabriel and his oldest son Anderville made the fatal mistake of drinking from the lake.  At this point, they were out of supplies and then made a slight detour for Yreka, California.  They then continued on their journey and arrived at their destination (now Jacksonville, Oregon) on October 13 or 14, 1852.  The family settled briefly in makeshift housing in the mining town.  Although they had reached their destination, it was not an easy time for them.  Gabriel and Anderville had both contracted typhoid fever from drinking contaminated water at Goose Lake – and they were soon on their death beds.  Gabriel died first, on November 14 (just one month after arriving) and his son Anderville died one month later, on December 22. 

The Plymales were now in a difficult situation.  Polly Plymale had uprooted her life and her family to follow her husband’s dreams of mining for gold.  Now her husband and eldest son were dead, she was in a strange place and had no way to support her family of 9 children.   They remained in their camp in Jacksonville throughout the winter of 1852-1853.  During this time, she apparently decided to make the most of her situation and remain in the area to do what she knew best: farm.  In the spring of 1853, the family went into the valley east of Jacksonville and claimed a farm of 320 acres.  The family built a house and soon cultivated a successful ranch on their land claim. 

Gabriel Plymale's headstone in the historic
Jacksonville Cemetery - the oldest one in the
cemetery.  He died exactly one month after
arriving on the Oregon Trail from Illinois, leaving his
widow alone in a strange place to care for their children

The Plymale Cottage in Jacksonville (built in 1868) is named after the family of Polly’s son William Plymale, who lived in the house with his family between 1890 and 1904. 

Many years after their emigration, Polly's son William Plymale wrote an article called "The Unknown" which described an incident in an 1852 Oregon Trail migration.  Although he doesn't explicitly describe being on the train, it was most likely the wagon train that the Plymales traveled in (he was then 15 years old).  Most of the article described an incident where a wagon train traveling ahead of them was ambushed and attacked by Indians near Tule Lake, in northern California.  When they arrived at the location a day or two later, it was a scene of bloody carnage and they had nothing to do but bury the dead and proceed on their way.  They were escorted by a military guard who had come too late to save the earlier train from attack.

References:

Plymale, John F. The Plymale Family in America. Commercial Printing & Lithographic Co., Inc., Huntington, WV, 1967.

Genealogical Material in Oregon Donation Land Claims, Vol. III. 1962

"History of the Zigler-Plymale Families."  Written in 1964 by Claud A. Zigler (grandson of Gabriel and Polly Plymale).

Tombstone inscriptions, Jacksonville Cemetery, Jacksonville, Oregon

Other:

1845 - Martin and Knighton

As described above, In 1844 William Martin returned to Missouri from an expedition trip to Oregon and California and began trying to convince his family and relatives to move out west.  He was able to convince his brother Hardin Martin and his sister Elizabeth Knighton to move out west first with their families.  Hardin and Elizabeth were able to get everything in order to leave in 1845.  

The wagon train they traveled in included 293 people in 66 different wagons.  It started from St. Joseph, Missouri sometime in April or May 1845.  Hardin Martin was the lieutenant of the wagon train company.  In the party included Hardin Martin, his wife Eveline Martin, his nephew William Martin, sister Elizabeth Knighton; her husband Henry Knighton and their daughters Josephine and Lascelle Knighton.  

The family safely arrived in northern Oregon in the fall of 1845.  Elizabeth Knighton and her family remained in Oregon City, Oregon.  Hardin Martin though moved to rural Yamhill County, Oregon.  The following year, a wagon train arrived from Missouri which included their parents, two of their brothers, and various other relatives. 

1848 - Brodie

In 1848, Lodowick Brodie was a 48-year old farmer who lived with his family in Missouri.  He had a wife and at least 7 children at home.  (Lodowick Brodie was the brother of my great-great-great-great-grandfather David Brodie of Clarksville, Tennessee).  When gold was discovered in California in 1848, he decided to leave his family and go west in search of gold.  Apparently, "circumstances of embarrassing nature" compelled to him to leave his family (perhaps he had very bad financial problems).  The details of his journey to California are unknown.  Sometime in 1850 though, he decided to return east to his family.  Instead of going overland, he decided to make the trip by sea.  He left by ship from San Francisco and then traveled south to the Isthmus of Panama, and then by ship north through the Caribbean and Gulf of Mexico.  The destination was probably New Orleans, and then up the Mississippi River back home.  Unfortunately, he never made it home.  Lodowick died of illness in November 1850, while at sea.  Conflicting sources suggest he died either on the Pacific Ocean and or in the Gulf of Mexico.  He was buried at sea.

1871 - Murray

In 1871, my great-great-great-grandparents James Murray and Flora Bartlow Murray lived with their children on a farm in northern Illinois.  For unknown reasons, they decided to move to Oregon.  They were probably following the example of some relatives who had moved to Oregon previously.  The Murrays did not technically travel on the Oregon Trail.  Since their move was so (relatively) late, they were able to take advantage of the Transcontinental Railroad that had been completed in 1869.  The family left their home in northern Illinois and made their way west.  They made the journey by train from Council Bluffs, Iowa to San Francisco, California.  That span of the journey would have taken about 7 days (much quicker than the 5 or 6 months it would have taken in a wagon train).

In San Francisco, the Murrays boarded a ship to take them to Portland, Oregon.  During the sea crossing, there was such a violent storm off the Oregon Coast that their boat nearly sank.  Apparently, it was so traumatic that during the storm "some were just shouting, some were cursing and some was praying and some was singing."  The storm subsided though and the family made it safely to Portland.  From Portland, they acquired a wagon and team of oxen and made the journey by land south from Portland to what is now Medford, in southern Oregon.  There, they purchased a farm where James and Flora remained until their deaths.  The location of their original farmhouse is now the site of a Walmart.