His outspoken anti-federal stance as a member of the Maryland House of Delegates, the lower chamber of the General Assembly, (state legislature) led to his temporary arrest on May 14, 1861.

At the time of his arrest, Winans was returning on a Baltimore and Ohio Railroad train from an early session of the legislature that was being held in the western Maryland town of Frederick to avoid the Union Army-occupied state capital of Annapolis in April–May 1861 to consider the possibilities of state secession during the early decisive period of the American Civil War.

One of his first and more important tasks was to help the famous inventor and industrialist Peter Cooper, (1791-1883), of New York City build the new revolutionary "Tom Thumb" steam-powered locomotive, to eventually replace the horse-drawn rail cars then being pulled along the short route of the Baltimore and Ohio that had been built so far - from the city's waterfront temporary depot facing "The Basin" (today's "Inner Harbor") at East Pratt Street and South Charles Streets to the southwest 20-some miles to its first terminus at Ellicott Mills on the upper Western Branch of the Patapsco River.

Also in this productive year he built the "Columbus", his first double-truck car, which he immediately patented, even though it is widely known he stole the idea for after the original inventor failed to do so.

[citation needed] In 1835, Winans went into partnership with George Gillingham and in 1836 they succeeded to the 1834 lease of Phineas Davis and Israel Gardner of the B.

His steam locomotives, popularly known as "Crabs," "Muddiggers," and "Camels" were used all over the fledgling rail network of the burgeoning industrial northeastern United States, from the 1840s until after the turn of the 20th century.

The Winans engine designs impressed a Russian delegation, and he was asked by the Czar to build the Imperial railroad from Moscow to St. Petersburg.

Winans may have sold as much or more equipment in Russia as he did in the United States, with both future 20th Century "super-powers" now setting the stage by building up their industrial and transportation networks on a continental scale, unknown in the smaller countries and kingdoms of Europe.

Winans' son Thomas returned to build a Russian style estate in west Baltimore, named "Alexandrofsky", surrounded by a somewhat forbidding-looking wall which also enclosed an eclectic sculpture garden.

Further west, another country estate of Italianate design with fieldstone walls in future suburban Baltimore County overlooking along the Gwynns Falls stream valley named "Crimea", off the Franklintown Road.

"Alexandrofsky", located near what is now the Hollins Market, built in the 1830s, was demolished a century later to expand the housing stock of the city and fill in the regular street grid of white marble-stepped brick rowhouses.

Luckily, twenty-three boxes of Winans papers and journals were donated to the Maryland Historical Society in the old Enoch Pratt mansion on Park Avenue and West Monument Street in Mount Vernon-Belvedere neighborhood for safekeeping.

Surrounding the estate is the remnants of an intriquing cannon embankment with slotted places for carved logs resembling iron artillery pieces, supposedly Winans' attempt to deter Northern troops from camping on his grounds, a testimony to his infamous pro-Southern sympathies.

A clap-board Gothic stylish small chapel also exists on the grounds along the entrance road, Eagle Driveway from West Forest Park Avenue.

Ten "Camels" were delivered to the Baltimore and Susquehanna Railroad, which was running its lines from the north near Harrisburg, Pennsylvania including one "engine sold them from Maryland Mining Co., $8000 cash."

Winans' arrest, by Benjamin Butler's Federal troops, was one of the cases where Lincoln's emergency suspension of habeas corpus was employed.

It passed through Winan's machine shop during the period when his workers were making pikes, shot and other items ordered by city authorities.

Though this novelty ultimately had no military impact, it was widely discussed at the time and its connection to Winans, along with his political views reputation as a threat to federal control of Maryland.

The Colonels reported back favorably on American Railroad practice, and recommended Major George Washington Whistler as consultant for the project.

Also, Eastwick and Harrison of Philadelphia introduced the equalizing lever, a spring suspension that distributed the engine's weight over three points.

In this arrangement, each of the four driving wheels could bounce independently as the engine negotiated rough track, greatly improving stability and traction.

Thomas Winans followed in his father's footsteps, and was on a trip to deliver locomotives to the Boston and Albany, when he met George W. Whistler.

The Winans Brothers and Harrison bought out the interests of Eastwick, and formed a company for operations and future railroad construction.

A financial crisis in 1865–66 lead to the Russian Finance Minister initiating a special Railroad Fund to ensure continuity of operations.

The Czar raised some money by selling Russian America (Alaska) to the Americans, and decided the privatization of the railroad would proceed.

This ship was discussed at length in the pages of the "Scientific American" national journal/magazine, and in the end remained tied up at the Winans docks at Ferry Bar, southside of the Whetstone Point peninsula and along the north shore of the Middle Branch or Ferry Branch of the Patapsco River, just west of old Fort Covington and Fort Babcock which supported Fort McHenry in the September 1814 Battle of Baltimore during the War of 1812 for many years, (later the site of the Port Covington railroad and harbor piers of the Western Maryland Railway built in the late 1890s and early 1900s) after a series of trials and modifications.

After the Civil War, Winans and his son took their enterprise to Europe, and several similarly designed boats were built in England and in St. Petersburg, Russia.

The Russian Shipbuilding Technical Committee were not impressed.. Winans then proposed to the U. S. Government the design of his ships, in what he saw as a pending conflict with England.

Winans took his cigar boat construction to England with his experimental Russian craft loaded on the British steamboat Nautilus.

Winans took an interest in sanitary engineering and public health, publishing a number of pamphlets on sanitation, particularly in regard to water and ventilation.