The steamboat Enterprise demonstrated for the first time by her epic voyage from New Orleans to Brownsville, Pennsylvania, that steamboat commerce was practical on the Mississippi River and its tributaries.Western Courier [Louisville, Ky.], June 1, 1815:"Arrived in this port, in 25 days from New-Orleans, the Steam-Boat Enterprize, capt. SHRIEVE. The celerity and safety with which this boat descends and ascends the currents of these mighty waters, the improvement of the navigation of which is so advantageous to the western world, must be equally interesting to the farmer and the merchant. The facility and convenience of the passage, in ascending the rivers, are such as to give a decided preference to this mode of navigation, while the size and construction of the boat entitles it to all the advantages which the Ætna and Vesuvius have in vain attempted to monopolize over the free waters of our common country."American Telegraph [Brownsville, Pa.], July 5, 1815:"Arrived at this port on Monday last, the Steam Boat Enterprize, Shreve, of Bridgeport, from New Orleans, in ballast, having discharged her cargo at Pittsburgh. She is the first steam boat that ever made the voyage to the Mouth of the Mississippi and back. She made the voyage from New Orleans to this port, in fifty four days, twenty days on which were employed in loading and unloading freight at different towns on the Mississippi and Ohio, so that she was only thirty four days in active service, in making her voyage, which our readers will remember must be performed against powerful currents, and is upwards of two thousand two hundred miles in length.": "The members of a committee of Congress reporting early in 1816 must have had the achievements of the Enterprise particularly in mind when they declared that the success of steamboat navigation on the Ohio and Mississippi rivers was no longer in doubt."

Early days The Enterprise, or Enterprize, with an engine and power train designed and built by Daniel French, was launched before June 1814 at Brownsville for her owners: the shareholders of the Monongahela and Ohio Steam Boat Company.Pittsburgh Gazette, June 10, 1814, p. 2: "THE PITTSBURGH GAZETTE.FRIDAY, JUNE 10, 1814.Arrived here on Wednesday morning last from Brownsville, the Steam Boat ENTERPRIZE, Capt. Gregg. Her destination the Falls of Ohio."American Telegraph [Brownsville, Pa.], July 5, 1815:"Last Saturday evening the Steam was first tried on the Despatch, another steam boat, lately built in Bridgeport, and owned as well as the Enterprize, by the Monongahela and Ohio Steam Boat Company. We are happy to learn that she is likely to answer the most sanguine expectations of the ingenious Mr. French, the engineer, on whose plan she is constructed." The Enterprise, under the command of Israel Gregg, was first used to transport passengers and cargo to ports between Brownsville and Louisville, Kentucky.Pittsburgh Gazette, June 10, 1814, p. 3:"THE ELEGANT STEAM BOAT,ENTERPRIZE,Captain ISRAEL GREGG,arrived here on Wednesday last, from Bridgeport, on the Monongahela, a distance of upwards of 65 miles, in 5 hours and 38 minutes. She is handsomely fitted up for passengers, and will take freight and passengers for Louisville, Falls of Ohio, for which place she will sail on Saturday or Sunday morning next. For particulars apply to the Capt. on board at Market Street Wharf. Pittsburgh, June 9th."Western Courier [Louisville, Ky.], June 27, 1814:"Arrived here on Tuesday last from Pittsburgh, the Steam Boat ENTERPRISE, Capt. Gregg." From June to December she completed two voyages from Louisville to Pittsburgh that were performed against strong river currents. With these voyages the Enterprise demonstrated for the first time that steamboat commerce was practical on the Ohio River.

Voyage to New Orleans On December 2, General Andrew Jackson had marched from Mobile, Alabama, to New Orleans with orders to oppose an imminent military invasion by an overwhelming British force.: "On the 2d December, general Jackson arrived at New Orleans, where he established his headquarters.": Smith described in detail the British expedition as "a fleet of sixty great ships", "Nearly one half of these vessels were formidable warships, the best of the English navy," that had transported "not fewer than eighteen thousand men [including 14,450 soldiers and sailors], veterans in the service of their country in the lines of their respective callings, to complete the equipment of this powerful armada." Jackson had been making frequent requests for military supplies, especially small firearms and ammunition, that were in short supply.: [Excerpt of a letter of December 16 from Andrew Jackson at New Orleans to James Monroe, Secretary of War.] "We have no arms here – will the government order a supply? If it will, let it be speedily. Without arms, a defense cannot be made." To this end, the shareholders made the decision to send the Enterprise.American Telegraph [Brownsville, Pa.], Wednesday, December 14, 1814:"The Steam Boat Enterprise of this place, which has been trading since last June in the Ohio, arrived here last Sunday afternoon. We understand that she performed the voyage from Steubenville to Pittsburgh, with a full cargo, in about three days; she made the passage from Pittsburgh to Brownsville, a distance of 65 miles, in about 17 hours. When the strength of the current is taken into consideration, it will be seen that she is equal to any boat in use. She will return to Pittsburgh in a few days, whence she will take freight and passengers, for New Orleans."Major Abraham Edwards to James Monroe, Secretary of War, February 11, 1815:"Report of the departure of boats, loaded with munitions of war, from this place [Pittsburgh] to Baton-Rouge and New Orleans and the names of persons in charge of the stores."National Archives DNA-RG 107, E-1815, microfilm 222, reel 15Western Courier [Louisville, Ky.], January 4, 1815:"Passed the Falls [Falls of the Ohio at Louisville, Ky.] on the 28th ult. the Steam Boat Enterprise, loaded with public property, consisting of 24 pounders, carriages, shells, small arms &c. for Gen. Jackson's army." Command was transferred to Henry Miller Shreve, a Brownsville resident and experienced keelboat captain, who had firsthand knowledge of the hazards to navigation of the Ohio and Mississippi Rivers.New Orleans Wharf Register:On February 11, 1814, payment of the wharfage fee, in the amount of "$3", for "1 barge" registered to "henry Shrive" was recorded. On December 21, 1814, the Enterprise departed Pittsburgh bound for New Orleans with a cargo of "Cannon-balls, Gun-Carriages, Smith's Tools, Boxes of Harness, &c".Edwards letter of February 11, 1815, to James Monroe, Secretary of War, lists the date – ranging from November 11, 1814, to January 15, 1815 – when each of nine boats departed Fort Fayette at Pittsburgh with military supplies for the American forces at New Orleans. It also lists the name of each boat's owner and the person "in charge of the stores", the type of military supply, and remarks regarding the progress made by three of the boats.Pittsburgh Mercury, October 23, 1822:"In consequence of the most unremitted exertions, the steam boat Enterprize, laden with munitions of war, and other supplies purchased with the private funds of Mr. Foster, was despatched from this place [Pittsburgh, Pa.] on the 20th of December 1814..." On December 28, the Enterprise passed the Falls of the Ohio at Louisville, delivering the cargo of military supplies at the port of New Orleans on January 9, 1815.Niles' Weekly Register [Baltimore, Md.], February 4, 1815, vol. 7, p. 361:"It appears that the steam-boat Enterprize, and a keel boat, passed Louisville, Ky. about the 28th of December, with arms and various stores for New Orleans, and we fear it is so that gen. Adair's men are without arms. However Jackson's fertile genius make them useful, or, perhaps, partially supply them."American Telegraph [Brownsville, Pa.], March 29, 1815:"The Enterprize has been employed in the public service for some time. She arrived at New Orleans on the 9th of January, one day after the battle, laden with amunitions [sic] of war, and it appears from the following extract of a letter from one of the officers on board, that she has given entire satisfaction, she exceeds in speed any other vessel that has yet floated in those rivers, she is a vessel of 50 tons burthen."

Battle of New Orleans

Under normal circumstances, the voyage by the Enterprise into Louisiana's waters would have been a violation of the territorial steamboat monopoly granted to Robert R. Livingston and Robert Fulton.Stecker, pp. 16–27Hardin, p. 32:"At an early day after his patent had been obtained, Fulton associated himself with Robert R. Livingston, of New York with the view of monopolizing the trade of the Western States and Territories. Failing to procure a charter from several Legislatures to which they applied, they finally obtained, in 1811, a legislative franchise from Orleans Territory, granting to them the exclusive right 'to navigate all vessels propelled by fire and steam on the rivers in said Territory.' This was granted by Chapter XXVI of the Acts of Second Session, Third Legislature of the Territory of Orleans, April 19, 1811, p. 112." However, the Enterprise was protected from the monopolists and free to navigate the state's waters by the martial law imposed by General Andrew Jackson on December 16.Mississippi Republican [Natchez, Mississippi], December 21, 1814

Despite the military supplies delivered by the Enterprise, Jackson's forces were still in dire need, particularly for small firearms, gunpowder and shot.: "On the fourth of January the entire body of Kentucky militia reached New Orleans, twenty-two hundred in number,…There were, at this time, nearly two thousand brave and willing men within Jackson's lines, whose services were lost to the army and the country for the want of arms.Though he [the quartermaster at Pittsburgh] was offered a contract to ship these supplies by a steamboat, and to deliver them at New Orleans in ample time for use, for some reason he declined the offer. He then had them floated on a flatboat and slowly floated to their destination, when there was little or no hope of their arrival in time for use." Responding to reports that several boats laden with military supplies were near Natchez, Jackson sent the Enterprise.American Telegraph [Brownsville, Pa.], February 22, 1815:"On January 20, 1815 an officer on board the Enterprise at Natchez wrote, 'When we arrived at New Orleans we were immediately pressed by General Jackson and are now in search of some boats loaded with U. States Arms.'" The boats were located and the Enterprise took them in tow, delivering them to New Orleans.

Then the Enterprise made another voyage to Natchez and returned to the port of New Orleans by February 12, 1815, when she was entered for the first time in the New Orleans Wharf Register as "Steam Boat (le petit) Captne Shrive".New Orleans Wharf Register:On February 12, 1815, payment of the wharfage fee, in the amount of "$6", for the "Steam Boat (le petit) Captne Shrive" was recorded.a. le petit is French for both "the little" and "the little one".b. Captne is a contraction of "Capitaine" that is French for "Captain".c. On February 12, 1815, there were two steamboats at the port of New Orleans: Enterprise and Vesuvius. Apparently, the name of the Enterprise was not known to the officials at the port of New Orleans so she was distinguished from the much larger Vesuvius by the entry "Steam Boat (le petit)", meaning either "Steam Boat (the little)" or "Steam Boat (the little one)".