the influence american indian pathways had on connecticut transportation systems settlements l.
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The Influence American Indian Pathways had on Connecticut Transportation Systems & Settlements. How this all got started….

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how this all got started
How this all got started…
  • “For many years before Connecticut was settled, there was a traveled way leading up from the shores of the sound east of the Norwalk River. Passing through Georgetown then heading due North to the land of Pah-quio-que (Danbury) the dwelling place of the southern tribe of the Schaticoke Indians…”

~Wilbur F. Thompson, April 1919 “The Old Indian Trail”

how this all got started looking deeper
How this all got started…Looking deeper
  • “The first Connecticut highway was, so far as we know, the Indian Trail…” ~Lewis E. Stanton, “History of Highways in Connecticut”
  • “While the water courses may be aptly termed the primary Indian Highways in New England, there were also many economically important overland trails throughout the area.”

~Leaman F. Hallett, “Indian Trails and Their Importance to Early Colonists”


And these are

only the main

foot paths!!

indian foot paths
Laid & developed through ages of Indian use with an eye to the easiest & quickest topographical [route], many of these ancient Indian foot paths were [later] adopted and enlarged into the bridle paths [by] the early pioneers, and eventually [became] the modern highways of today.

~Leaman F. Hallett, “Indian Trails and Their Importance to Early Colonists

Indian Foot Paths
indian foot paths8
Seasonal rotations from planting grounds to fishing & hunting grounds were made over these paths … with inter-tribal communication along the way. Ordinarily there were two main paths running perpendicular to each other: North-South, East-West, quartering each tract. ~Leaman F. Hallett, “Indian Trails and Their Importance to Early ColonistsIndian Foot Paths

East-West Path

Routes 112, 182, 183, 20, 219, 190

North-South Path

Routes 7, 202, 126

East-West Path

Routes 6, 317, 67

North-South Path

Route 5

Albany Turnpike

paths to connecticut
On April 4, 1631, John Winthrop, Jr. recorded in his Journal that “Wahginnacut, a Podunk Sachem on the River Quonehtacut…came to Boston and said he was very desirous to have some Englishmen come plant (settle) in his country…which is not above 5 days journey from us [Boston] by land.”

~Winthrop Journal, I: 223

Paths to Connecticut
roger ludlow settles the ct river valley
In 1633 trader John Oldham & three companions traveled to CT and came home to MA with a positive report:

“The Sachem used them kindly…they traded for beaver, hemp and black lead (graphite)…they lodged in Indian towns the whole way.”

This report followed by a treaty offer from the Pequots led Roger Ludlow overland to present day Greater Hartford Area in June of 1635 with his Dorchester Association members. Ludlow followed the Connecticut path of the Indians, now Routes 44, 197, 198.

Roger Ludlow Settles the CT River Valley

Springfield, MA

Ludlow’s Route

Routes 44, 197, 198



Indian Paths become modern highways

Springfield, MA

Route 190

Route 197

Route 5

Route 140

Route 198


Route 44


Route 6


Route 2

pequot war opens coastal settlements
In 1636 trader John Oldham was killed on Block Island. To avenge his death the Bay Colony set out to attack the Narragansetts for the murder and the Pequots for their lands. The Pequots had nothing to do with the murder.

By this time there were two settlement areas in CT, Hartford & Saybrook. In response to the Bay Colony’s attack, the Pequots attacked Saybrook & Wethersfield, killing settlers in Wethersfield. Thus began the Pequot War.

Pequot War opens Coastal Settlements
pequot war opens coastal settlements18
Ludlow declared an “offensive war” on the Pequots & with the help of Uncas’ Mohegans and soldiers from Massachusetts Bay they chased the Pequots all over CT, until they finally cornered them in a swamp at modern day Southport where it all ended horribly for the Pequot tribe. Pequot War opens Coastal Settlements



Coastal Settlements

Quickly follow the

Pequot War






*Roger Ludlow purchased land in Saugatuck &

Norwalk (1640) but it wasn’t settled until later.


Indians Pushed

Inland as Settlers

Take Over Their

Coastal Villages

land sales oversight or misunderstanding
European settlers continually ignored important text in the Indian‘s portion of the deeds:

"Reserving in the whole of the same, liberty for myself and my heirs to hunt, fish, and fowl upon the land and in the waters, and further reserving for myself, my children, and grand children…the use of so much land by my present dwelling house or wigwam as the General Assembly of the Colony … shall judge necessary for my or their personal improvement...”

Land Sales… Oversight or Misunderstanding?
different viewpoints
Indians did not understand land ownership the way the English and their future generations viewed it: in their culture, no tribe nor Indian had exclusive, permanent rights to specific parcels of land, "different groups of people could have different claims on the same tract of land depending on how they used it." By ignoring the Indian’s provisions within the land deeds, the settlers were exceeding the usage rights the Indians were granting them. Different Viewpoints
different viewpoints23
“What the Indians owned or had claim to- was not the land but the things that were on the land during various seasons of the year…In nothing is this more clear than in the names they attached to their landscape, the great bulk of which related to usage not possession.”~William Cronon, Changes in the LandDifferent Viewpoints
meanings of indian names
Pok-a-no-ket: “at or near the cleared lands.”

A-bess-ah: “clam bake place”

Mitt-in-eag: “abandoned fields”

Eack-honk: “the end of the fishing place”

Simpaug: “beaver pond”

Aspetuck: “at the high place.”

Ousatonic: “land beyond the mountains”

Waramaug: “good fishing place”

Pequonnock: “a small plantation”

Mash-an-tucket: “in the little place of much wood”

Meanings of Indian Names

Oyster Shell Pile!

You can see why coastal tribes

would not want to leave their lands!!

early interior settlement
Derby is settled in 1651. Indian Trails and a Ford where the Naugatuck meets the Housatonic.

Woodbury is settled in 1672. Indian Trails lead these coastal settlers to the interior.

Settlers make their way from Norwalk to Danbury in 1684 to establish a town. Indian Trails lead these coastal settlers to the interior.

Early Interior Settlement

From 1639 to 1651 there are no English settlements

in the Western interior of Connecticut…at least that I am aware of…That changes once Derby, Woodbury & Danbury are settled.





Indian trails used in all these migrations

indian guides were essential
In finding their way inland, settlers needed Indian guides to find where the Indian paths were and where they went. One writer noted: “they (the English) sadly search up and down for a known way, the Indian paths not being above a one foot road. So that a man may travel many days and never find one.”The use of guides would continue into the 1800’s. i.e. Lewis and Clark Expedition.Indian Guides Were Essential



Waterways = Early

Indian North/South




Naugatuck R. meets Housatonic R

Fording place.


The simplest early roads were described as “paths cut out” i.e. brush was cut out along the Indian pathways and trees were marked with an ax…


Later these paths were made “passable for horses” by cutting tree limbs high enough to permit the passage of a horse and rider. For many years this was the method of travel throughout our state. Pack horses became common and goods were often transported by packhorse trains…


The next progression, which proves to be an important one, was the widening of bridle paths to accommodate Ox Carts. Oxen were strong and capable of travel over terrain that would be impassable for a horse-drawn cart…


Packhorse lobbyists protested heavily, claiming the construction of wider roads was a waste of taxpayers’ money but they lost and as a direct result of these new Ox Cart paths, inland settlements in our State increased quickly.


Ox Cart Paths Improve Travel & Access to the Interior Lands

This Assembly doth free the town of Danbury from paying country rates this present year (1702), They paying their deputies salary and all other Public charges amongst themselves, and they making a sufficient cart-way from their town and through their bounds and the country lands, for transportation of what they raise to the sea (i.e. the ports of Fairfield and Norwalk).




New Milford







Pioneer Settlement


Settlements resulting from success of & improvements by pioneer towns





indian paths noted in many town histories
The first (New Fairfield) settlement was established in a small valley… Paths, later roads, radiated out from this central settlement to outlying lands taken by settlers

An extensive network of trails interlaced Newtown’s interior area and connected to the Housatonic River at numerous points.

Early (Bridgewater) roads followed paths and later evolved into the irregular topography-dominated network which exists today.

Indian Paths Noted in Many Town Histories
colonial postal route
Indian Paths played a major role in the establishment of the postal system in this country. The first colonial postal route was started by a single rider, in the winter of 1673, who rode between New York and Boston with a horse change in Hartford, his route traveled was over the old Indian trails between these points. Travel time? 3 weeks!Colonial Postal Route
colonial postal route49
The three major alignments of this “The Boston Post Road”were the Lower Post Road (now U.S. Route 1 along the shore and through Providence, Rhode Island), the Upper Post Road (now US 5 and US 20 from New Haven, Connecticut via Springfield, Massachusetts), and the Middle Post Road (now Route 44 which split from Hartford, Connecticut, and ran diagonally to Boston via Pomfret, Connecticut).Colonial Postal Route

Route 44

Middle Post Road

Upper Post Road

Route 5

Lower Post Road Route 1

the early postal system
In 1692 an attempt was made to establish postal service to Virginia which failed.

By 1717 mail was being carried from Boston to Virginia. Travel time? One month in Summer; Two months in Winter.

Philadelphia was added in 1720, receiving mail from New York once a week.

1754- Benjamin Franklin named Colonial Postmaster. Reduces trip from New York to Philly from 3 days to a day and a half.

The Early Postal System
the early postal system52
The Early Postal System
  • By 1765 the postal system of the colonies had grown from a single post rider to about 60 post offices, almost all of which were on the coasts or not more than 60 miles inland.
  • Ben Franklin stated: "...The posts only go along the sea coasts; they do not, except in a few instances, go back into the country..."
colonial postal route53
Colonial Postal Route
  • Franklin likely noted this because Inland roads in the colonial period were poor, as colonists did not have modern conveniences such as bulldozers and excavators to clear pathways for their travels. Trees and bushes were cut back with hand-tools and oxen teams were harnessed to remove stumps and boulders in order to widen the existing footpaths.
colonial postal route54
Colonial Postal Route
  • Once mail reached a point on the "coastal" Post Road close to its destination, it would be sent inland via post rider, or it would wait for someone who was traveling in the direction of the addressee to pick it up and carry it the rest of the way inland.

Inland Post


Post Road

the post rider
The Post Rider was a man of importance in our rural communities, delivering the weekly newspaper and some letters. He traveled on horseback, and was often accompanied by one or two pack horses. He acted as a middleman between local farmers and city dealers, taking the smaller products of the farms - butter, cheese, honey, beeswax, woolens, yarn, flax, etc., to the larger towns - selling them, and bringing back dyestuffs, calicos, needles, pins and other articles used in the rural homes of that day. The Post Rider
the post rider57
Postmasters and post riders were exempt from military duties so as not to interrupt service. These post-riders were allowed the exclusive privilege of carrying letters, papers and packages on their respective routes, and any person who infringed upon their rights was subject to a fine. So in addition to their $100 a year salary, many Post Riders operated side-businesses along their “exclusive routes.”The Post Rider

To Boston


Albany Turnpike

New London

New Haven

To Providence

Post Road

apparently our roadways were in need of some improvement
Dr. Samuel Holton in June, 1778, went from Boston to Philadelphia. The only route he describes as “very good,” was the one from Springfield to Hartford. From Hartford to Litchfield the roads were “very bad,” while the roads from Litchfield to the New York Line were the “worst he had ever seen!”

Count Chastellux who went through Connecticut in 1780 remarked that in going from Canaan to Norfolk “you mount for 4 or 5 miles continually bounding from one large stone to another, which cross the road & give it a resemblance of stairs.”

Apparently Our Roadways Were in Need of Some Improvement…

Some Indian Paths just

weren’t made for Turnpikes

the turnpikes
Turnpikes came into Connecticut in the 18th and 19th centuries. During this period a large number of turnpike companies were being chartered by the General Assembly in towns and cities throughout Connecticut. The turnpikes were very superior to the old cart paths, generally having straighter alignments, lesser grades, bridges instead of fords, and graveled surfaces. The Turnpikes
the turnpikes65
Most turnpikes were two-way thorough-fares, about twenty-four feet wide and relatively straight. In New England, in order to avoid muddiness and road erosion, drainage was provided by giving the road a convex surface to shed the water. Connecticut companies tended to spend less money for turnpikes than those in states such as Massachusetts, since many turnpike corporations simply improved existing public roads and therefore avoided heavy expenditures for rights of way.The Turnpikes
early turnpikes of connecticut
One of the first highways to come into general use was known as the “high road to Albany”, this ran from Hartford to Farmington, Harwinton, Litchfield, Goshen, Cornwall, Canaan, Salisbury and on into New York.Another East-West route ran from Waterbury, Woodbury, through New Milford and on into New York.These highways pushed Connecticut products to the Hudson River and diminished trade within our State. Early Turnpikes of Connecticut
early turnpikes of connecticut67
To touch on some other Turnpikes of interest… Running North-South was the Hartford & New Haven Turnpike running down though Farmington, Southington, Cheshire. Hamden and on into New Haven. James Hillhouse directed the building of this road and later was the superintendent of the Farmington Canal project. Early Turnpikes of Connecticut

East-West Path

Routes 112, 182, 183, 20, 219, 190

North-South Path

Routes 7, 202, 126

East-West Path

Routes 6, 317, 67

North-South Path

Route 5

Albany Turnpike

early turnpikes of connecticut69
Other Turnpikes of interest… Running North-South, The Waterbury River Turnpike was chartered in 1801-02. It ran from Naugatuck to Waterbury, then north through- Thomaston, Torrington, Winchester, West Windsor, Colebrook and then crossed the border to connect to the Massachusetts 15th Turnpike Early Turnpikes of Connecticut
stage coaches
With the *improvement of roads, stage coaches appear in the early 1800s.Advertisement by the New Post-Coach Line Dispatch:“6 hours from Hartford to New Haven, leave Hartford at 11am and arrive in New Haven at 5pm.” …and you thought your commute was bad! Stage Coaches
stage coaches71
*Road Improvement wasn’t always a given…“In some of these ancient roads the passenger was jolted and distressed going down hill as well as up. In one case an occupant of the Stage Coach called out to the driver- ‘Are you going down any further? For if you are…I must get out, for I do want to remain on this earth a little longer.’Stage Coaches

No Fear here!


Stacked three levels high



taverns postmasters
Taverns & Postmasters
  • In this period Taverns often doubled as Post Offices.
  • Why?
  • Stagecoaches stopped regularly at Taverns. The two were a perfect match for mail transportation, drop-off and pick-up.
turnpikes milestones
In the summer of 1763, Ben Franklin completed a five-month carriage tour to inspect post offices. On that tour, he utilized an odometer. The Institute News describing the action of his odometer noted: "When actuated from a carriage wheel having a circumference of thirteen and one-fifth feet, a mile was registered in each four hundred revolutions. If wired to the top of the front axle at the right hand side it was easily set in operation by a hub-type projection on a hub or spoke and the dials were readily visible to both driver and rider." Turnpikes & Milestones

12 MS (Miles) to NW (Norwalk) 1786 On South Street in Danbury, there is a milestone bearing the date of 1787, "67 miles to New York, 67 miles to Hartford"


Hartford to Poughkeepsie

Stage Route Marker

too slow and too expensive
Average freight costs in 1820 were about 15 cents a mile per ton, more than twice as much as water transportation. By 1825 more than half of the turnpike ventures in the country had been either partially or totally abandoned. A contributing factor to the failure of these internal overland routes was the emergence of the canal.Too Slow and Too Expensive

Canals…“a method of transportation superior to any previously known.”~Charles R. Harte, Connecticut’s Canals


Efforts to Establish a

Connecticut Canal System

Extending from Albany to Buffalo, the Erie Canal was completed on November 4, 1825 and soon became a great commercial success.

Before its completion the cost of shipping 1 ton of cargo between Buffalo & NYC ranged from $90 to $125. Within 10 years of the Erie Canal’s completion, the cost had dropped to $4 per ton.


Efforts to Establish a

Connecticut Canal System

The wave of enthusiasm that followed the success of the Erie and other canals did not escape the entrepreneurs viewing the productivity & transportation needs of Connecticut. By the early 1820s a total of six (6) canals were proposed for Connecticut. Two (2) would be constructed and placed into service: The Farmington and Enfield Canals.









Connecticut’s Proposed Canal System

  • New York and Sharon Canal
  • Ousatonic Canal
  • Saugatuck & New Milford Canal
  • Farmington Canal
  • Enfield Canal
  • Quinebaug Canal

Impressive Numbers!

Four million pounds of merchandise were shipped every month from New Haven, through Hamden, Cheshire, Southington, Bristol, Farmington, Simsbury, and Granby, bound for Northampton, Massachusetts, on the Farmington Canal. At three every afternoon, packet boats left the Elm City docks in New Haven, making the trip to Northampton in the unheard-of time of twenty-four hours. The age of canals had arrived in Connecticut.


Water Issues, Debt and the Railroad

From 1835 to 1847 the canal suffered extraordinary damages from flooding. Repairs were constant and debt ran high. 1845 looked to be the year they turned the corner but it turned out to be their most disastrous as a drought interrupted service from mid-July to late September.The Company turned its attention to the practicability of building a railroad.

After 1847, the Farmington Canal was never operated through its total length again.


Housatonic RR completed 1841

Originally chartered as the "Ousatonic" Railroad in 1836, the charter allowed the company to build either north towards Massachusetts, or west towards New York City.

The Housatonic Railroad began construction in 1837, the task was to convert miles of rugged landscape along the Housatonic River into an iron trail that could not exceed a 1% grade…via human labor. There was not any specialized equipment, hardy souls and hand tools would be the only tools employed in the railroad's construction.


Housatonic RR

Early Indian Trails

later used

as “Iron Trails”

a.k.a Railroads



Falls Village

West Cornwall


Housatonic Railroad


New Milford


Danbury to Norwalk RR completed 1852

The Danbury to Norwalk Railroad began construction in the autumn months of 1850, the task was to convert 23 miles of rugged landscape along the Norwalk River into an iron trail that could not exceed a 1% grade…via human labor. Again, there was not any specialized equipment (not even black powder!), hardy souls and hand tools would be the only tools employed in the railroad's construction.


Early Indian Trails

later used

as “Iron Trails”

a.k.a Railroads


follows Indian Trail


1850s Map

Danbury to Norwalk


railroad workers pay 1851
Railroad Workers Pay- 1851

Why many workers looked for other work after

Railroad was completed



Stage Coach

looks for new

options of

which there

are few


Post Office moves to RR


1856 Map


RR’s 1893



Wilson Point on Long Island Sound

Crosses Long Island Sound by Steamship avoiding rail traffic on the NY/NH line

Shipped Trains

To Long Island

A 1882 Addition to Danbury/Norwalk Railroad. This leads to profitable

agreements with other RR’s & is a great benefit to businesses on the Danbury/Norwalk line.

Ice, Eggs/ Milk, Wire, Granite, Feldspar, Quartz all products that can now reach NYC ports quickly


Commodities came into Connecticut via the Railroad too

PoundsCommodity & Destination

  • Groceries- Litchfield
  • Salt and Cod- Redding
  • 200 Tea- Derby
  • 1050 Soap and Starch- Ansonia
  • 4800 Tobacco- Danbury
  • 900 Rags- New Haven
  • 1800 Eggs- Bridgeport

Routes 112, 126, 63

Route 5


What is amazing is that Indian Path

played a major role in all these

transportation systems


Route 44 & 198

Routes 41, 7, 202, 35


Route 6

Route 2

Route 5

Route 32

Routes 67, 317, 6


Routes 119, 34, 25,

and RR Line

Route 15

Route 1

Routes 7,

33, and

RR Line

Route 25