Initially built in 1853 by John Oades in Clayton, New York, as barkentine Northern Light for merchants John N. Fowler and Henry Esselstyn, the Northern Light initially operated in the Great Lakes grain and lumber trade. The Northern Light received sparse notice from the newspapers throughout its time working, and an identically named Canadian barkentine only muddles the historical thread further. The Northern Light briefly filled with water and rolled over on July 18, 1857, when the blankets used to keep water disengaged; it was easily raised and repaired. The ship received good work for the years leading up to its conversion in 1866. Starting in 1865, the barkentine Northern Light was rebuilt by Simon G. Johnston to add a second centerboard and was improved and lengthened, leading to it being renamed the Montgomery; however, the ship remained listed as barkentine rigged. The Montgomery continued to operate in the Great Lakes crop and lumber trade with little issue. Prudently, inconsistencies in reporting the Montgomery's (and other vessel’s) routes, cargos, and harbor arrival clearings were commented on in the Inter Ocean on September 8,1874, which explains why the ship avoided the press so well. The Montgomery was re-rigged into a canal schooner in 1881.

Starting in 1882, the Montgomery began participating in the Great Lakes ore trade, being towed by the tug Niagara. When the Montgomery was sold in 1887, the ship started to focus on shipping ore to Toledo, Buffalo, and various ports in Wisconsin. A series of accidents occurred in 1887, including the ship's foremast being carried away in October 29 and a grounding and filling with water on November 25. Otherwise, the Montgomery continued to work perfectly fine.
On the morning of November 5, 1890, while en route to Sheboygan with a cargo of coal, the Montgomery ran ashore during a gale, grounding and immediately filling with water. Despite flying distress colors all day, Coast Guard patrolmen did not sight the stranded ship, providing an apt parallel to the lack of attention it received in its 36-year history. No lives were lost, and the tug Sheboygan came to the ship's assistance the following day but failed to get the schooner free. The ship was deemed a total loss a few days later. The ship was stripped on November 9.
The location of the Montgomery site was forgotten until 1958 when skin divers, who were stationed at Camp Haven, located the wreckage and dove it in their spare time. The site became popular with divers in the 1970s; unfortunately, the exact location of the site was lost in the intervening years. The site was brought to the attention of the Wisconsin Historical Society in June of 2015 by Steve Radovan but was not located until 2018. WUAA volunteers and Society archaeologists documented the wreck in June of 2018. Today the Montgomery is located on a rocky bottom 0.45 miles east of the Whistling Straights Golf Course, in the town of Mosel, Sheboygan County, Wisconsin in 12 feet of water on the bottom of Lake Michigan. The vessel’s keelson and floors remain intact on the site along with its two centerboard trunks, and hull planking. As one of the few double-centerboard canal schooners in the Great Lakes, the Montgomery offers a unique study opportunity on the history of the Great Lakes.