In response to a question about bridges across the Connecticut River, I thought I'd post the answer as an article.
The photo is from a postcard, and shows the brief period of time when both the Old Toll Bridge and the Hampden County Memorial Bridge were standing. In a display of Yankee frugality, the Toll Bridge is being dismantled board by board.
These passages that follow were taken from King's Handbook of Springfield, edited by Moses King, 1884.
=== Begin Article
At the beginning of the present century frequent discussions took place between the people of Springfield and West Springfield about the feasibility of constructing a bridge across the Connecticut River. The business-men and middle-aged people had faith in the project; but the old men wagged their heads in opposition, one prominent rich man saying, " Gentlemen, you might as well undertake to bridge the Atlantic Ocean."
Finally, after much hesitation, the seemingly ponderous job was undertaken. The planting and rearing of the sub-structure was difficult: the two abutments and five piers had to be embedded in the river, and that without previous experience, or the use of modern appliances. Pile-driving was done by horse-power, as steam hammers were not then known to the world. A large floating platform was constructed, and anchored in the river near the site fixed for a pier; on it was placed the necessary machinery for raising the hammer; this was operated by a horse winding a rope around a drum, or cylinder. This horse "swung around the circle" from morning till night, from Monday till Saturday, and from spring till early winter; but no man has numbered the revolutions he performed, nor the thousands of miles he traveled during the process. On the platform was a stable for his shelter and repose at night; for he slept on the "bosom of the deep," not being taken ashore till the close of work for winter. Verily his memory is entitled to a monument. The site of the bridge did not occupy the place of any ferry, nor was it within 50 rods of any road or highway. The bridge company bought land on each side of the river for their approaches, the location being where the old toll, or wooden, bridge now stands.
The first bridge was opened for travel Oct. 30, 1805. It was 1,234 feet long, 30 feet wide, and 40 feet above low-water mark, and cost $36,270. It was uncovered, and painted red; and consisted of six arches supported by two abutments and five piers, each 21 feet wide and 62 feet long. Up the river, in the vicinity of the present railroad-bridge, were built three "icebreakers," or piers like the bridge-piers, with the up-stream sides sloping down to the water, designed to allow the immense sheets of ice in the spring to slide up into the air, and by their own weight fall down in smaller pieces, thus preventing the choking of ice under the bridge. The name of the designer or builder of this bridge is not now known. During the construction, by an accident several of the workmen were injured, and one killed: and also, in the month of March, several of the armorers crossed on the timbers of the framework, to the west side, on a spree, and in returning, late at night, one of them lost his balance, and was drowned.
The bridge was opened with imposing dedicatory exercises, a procession, prayer, sermon by the Rev. Dr. Joseph Lathrop of West Springfield, music, and the ringing of bells. When the procession reached the bridge, a national salute of 17 guns was fired three times; and 3,000 people, standing on the uncovered bridge, gave three rousing cheers.
This bridge was a vast accommodation to many towns on either side of the river, and was duly appreciated. But after nine years effective service it showed signs of weakening; and, after the spring freshets of 1814 had subsided, the company began strengthening the arches, and set up "horses " under the eastern span to support it while undergoing repairs. But on the 14th of July a heavy Pennsylvania wagon, heavily laden with army supplies from the east, attempted to cross. When the team had got well on to the bridge, the first span crippled and went down; but the "horses", or trusses, being equal to the pressure, held up bridge and team, so that the load was saved, and nobody killed. This ended travel across the bridge; and it was soon taken down, having become too much weather-beaten to endure longer service. It was mongrel in style, the travel being on neither the bottom nor top of the chord, but ascending and descending with the curve of the arches of each span.
The present bridge was constructed in 1816; the builder being Capt. Isaac Damon of Northampton, a man of great capacity for construction and superior workmanship, his work having stood the test of 67 years of strain as a bridge, and is now likely to stand 40 or 50 years longer. It was partially carried off by the spring freshet of 1818, and the lost portions supplied in 1820; but never since has it suffered by ice or water. At the last fracture in 1818 Gen. Bliss, one of the directors, thought to save the east end of the bridge, by securing an immense cable or rope to the main timbers, and fastening the rope to a large tree on the bank of the river above the bridge; but the next large sheet of ice that struck the bridge hardly straightened the sag of the cable before it parted, and away went the eastern span of Capt. Damon's superstructure.
The present is the second bridge, and was covered at the time of building. The travel is on an even plane at the bottom of the chord. The heavy pine timber of the arches was cut far up the river, rafted down, and hewed out by hand. Tolls were taken until July 1, 1872, when it was made free by Act of the Legislature.
The next bridge was that of the Western Railroad, completed July 1, 1841, made of wood, on the "Howe" plan, and uncovered. This was taken down in 1855, and replaced by another; the trains all the while continuing their usual trips. The second bridge was covered, and continued in use until the erection of the present iron bridge in 1873.
The North-End iron bridge was completed Sept. 1, 1877, and dedicated by a large concourse of people on the West-Springfield side. Dinner-tables were placed in the goodly shade of a row of maple-trees, refreshments offered to the crowd, and speeches made by the friends of the enterprise; William Chapman of West Springfield leading off with much enthusiasm. It affords the centre of that town an additional and more convenient privilege of access to the Union Railway Station. It is one of the handsomest highway bridges in the United States.
The South-End iron bridge, connecting the city with Agawam, was built in 1878, and completed and opened for travel Feb. 1, 1879. It takes the place of the old steam-ferry, and is a great advantage to the towns of Agawam, Suffield, Southwick, and Granby. From the above it will be seen that there are now four bridges across the Connecticut within the space of two miles and a half.
=== End Article
This explains the history of bridges until 1884. Of the four bridges mentioned, the only one still standing is the railroad bridge; all others were replaced. The Old Toll Bridge was replaced in 1922 with the Hampden County Memorial Bridge; the North End Bridge was replaced in 1925, and the South End Bridge was replaced in 1954.
This map, derived from Google Maps, shows the location of the Old Toll Bridge; it explains why Bridge Street has its name despite not currently leading to a bridge, as well as why there is a similarly unconnected Bridge Street in West Springfield.
Here is another photo of the Old Toll Bridge: