Captain Hilliard attended the academy of his native town, after which he began the study of medicine. This he continued for about three years, under his brother-in-law, Dr. Patchin. Disliking the practice of surgery, however he gave up the profession, and went to Canada, where he took command of one of the barges on the St. Lawrence River, plying between Prescott, Grenville County, Ontario and Montreal, Quebec. In this latter step he was influenced, in a great measure, by an account of the early life of his father.

He afterwards bought a farm and settled at Prescott; but, becoming restless in so quiet a life at the age of twenty-one, he purchased a barge, which he ran successfully for about two years and a half. He then engaged as purser and clerk on the steamboat "Great Britain", and held the position for about three years. In 1828 he became Captain of the steamboat "Brookville".

In 1829 he took charge of "William the Fourth", then the largest boat on Lake Ontario. Captain Hilliard continued to be interested in steamboats until 1852. During this time he was instrumental in opening the St. Lawrence River to navigation. He performed what had been considered an impossible feat, - that of taking a steamboat over the rapids of the St. Lawrence River. For this he was presented with a valuable gold watch, bearing the following inscription:
"Presented to Captain L. Hilliard, by John Hamilton, to commemorate the safe arrival of the steamboat 'Ontario' at Montreal, from Prescott, United States; having made the first descent by steam over the rapids of the St. Lawrence, 19 AUG 1840".

For a number of years, Captain Hilliard was engaged in a forwarding business, having in charge a large number of vessels, and living in Montreal and Toronto. In 1854 he removed with his family to Michigan. He made a short stay in Battle Creek, Calhoun Co., MI, engaging in the flour business in a limited way. He then went to Kalamazoo, Kalamazoo Co., MI; and in company with others, engaged in the lumber business at Dorr, Allegan Co.; but in the financial crash of 1857, he lost nearly all he had. In FEB 1861, he purchased a small piece of land and a saw-mill in the town of Hopkins, Allegan Co., and worked earnestly to retrieve his fortune. He made a second purchase of land, - about nine hundred acres - upon which he realized a net profit of thirty thousand dollars. He still continued to manufacture lumber, and to deal in real estate, until the time of his death in 1871. He left an unencumbered estate of about one hundred thousand dollars.

He was a member of the Congregational Church for the last thirty-seven years of his life; he was a faithful attendant and a liberal contributor. He was a Whig, and became a Republican upon the organization of that party, in 1854. Four of his children served in the Civil War.
Captain Hilliard was strong in his personal friendships, and genial to all.

He died of stomach cancer. (20 SEP 1871)

In the Revolutionary War Daniel served as a marine on board the ship "Oliver Cromwell" which captured the British ship "Admiral Cable" near Barbados. After his discharge he went to the Island of Saint Eustatius in the West Indies and enlisted JAN 1781 on the brig "General Washington." He was taken prisoner to Antigua on Saint John's Island and imprisoned nearly 11 months before being exchanged at Philadelphia. He also served from Vermont for which a pension was awarded.

They resided in Manchester, VT, where all their children were born. At some time after 1807, they removed to Plattsburg, NY, where they both died. The census of 1850, show Rebecca living with her son Marimus in Plattsburg, NY.

No date given in DAR reference.

1. Obediah HILLIARD b. 6 Oct 1786, Manchester, Bennington County, Vermont; d. 6 Jan 1828, Plattsburg, Clinton County, New York; bur. Schuyler Falls, Clinton County, New York (Hilyard Cemetery).
2. Fanny HILLIARD b. 2 Feb 1788, Manchester, Bennington County, Vermont; d. 18 Jan 1878, Plattsburg, Clinton County, New York.
3. Arna HILLIARD b. 15 Nov 1789, Manchester, Bennington County, Vermont.
4. Marinus HILLIARD b. 25 Jul 1791, Manchester, Bennington County, Vermont; d. 2 Apr 1855, Plattsburg, Clinton County, New York.
5. Harriet HILLIARD b. 26 May 1793, Manchester, Bennington County, Vermont.
6. Statira E. HILLIARD b. 25 Oct 1795, Manchester, Bennington County, Vermont; d. 15 Nov 1843, Plattsburg, Clinton County, New York.
7. Chloe HILLIARD b. 18 Sep 1797, Manchester, Bennington County, Vermont; d. 28 Aug 1856, Patten, Penobscot County, Maine.
8. Minor HILLIARD b. 29 Mar 1800, Manchester, Bennington County, Vermont.
9. 1. Lonson HILLIARD b. 17 Sep 1802, Manchester, Bennington County, Vermont; d. 2 Aug 1871, Hopkins, Allegan County, Michigan.
10. Abigail HILLIARD b. 14 Oct 1804, Manchester, Bennington County, Vermont; d. 20 Feb 1868, Schuyler Falls, Clinton County, New York.
11. Hiram R. HILLIARD b. 19 Dec 1807, Manchester, Bennington County, Vermont; d. 20 Jul 1844, Plattsburg, Clinton County, New York; bur. Schuyler Falls, Clinton County, New York (Hilyard Cemetery).
12. Daniel HILLIARD b. Abt 1820, Danby, Rutland County, Vermont; d. Aft 1890, Danby, Rutland County, Vermont (probably).

Norwich, March 21st 1742/3. This may Certife sd John Hylliard minor fourteen years of age son to Jonathan Hylliard Late of Stonington decec'd personally appeared and made Choice of Mr. Ephraim Kingsbury of Norwich to be his Guardian. Jabez Hide, Justice of peace
John's parents died when he was fourteen years of age. It appears that John went to Norwich to live with his cousin Joseph but possibly Joseph was not well enough (he died soon after) and recommended Ephraim Kingsbury to be his guardian. Following document is on record:

John and Elizabeth resided in New Concord Society (Preston), New London, CT. where he was baptized with his three eldest children, and with his wife owned the Church covenant, 12 SEP 1762. John, at an early date, settled in Manchester, Bennington Co., VT. About the year 1790 he came to Danby.

In reference [3:109] it is given that he died 24 JAN 1731/1732. That is the death of Ambrose.

The Barbour Collection has John dying Stonington, 24 JAN 1731/2. This date was actually the date that the next son, Ambrose, died. This has been very confusing to persons doing genealogy on the descendants of John and Elizabeth (Smith) Hillard. Apparently Mr. Barbour kept his information on cards with the birth on the front and the death on the back. The above error came about when the card of John and Ambrose stuck together.

1. Azariah HILLARD b. 23 May 1754, Norwich, New London County, Connecticut; d. Sep 1783.
2. Joshua HILLIARD b. 7 Jan 1757, Norwich, New London County, Connecticut; d. 27 Aug 1849, Plattsburg, Clinton County, New York.
3. 2. Daniel HILLIARD b. 31 Jan 1759, Norwich, New London County, Connecticut; d. 20 Nov 1834, Plattsburg, Clinton County, New York; bur. Schuyler Falls, Clinton County, New York (Hilyard Cemetery).
4. John HILLIARD b. 1761, Norwich, New London County, Connecticut; d. Bef 1768.
5. Minor HILLIARD b. 29 Apr 1764, Norwich, New London County, Connecticut; d. 28 Feb 1846, Danby, Rutland County, Vermont; bur. Danby, Rutland County, Vermont (Four Corners Cemetery).
6. Ednah HILLIARD b. 29 Apr 1764, Preston, New London County, Connecticut; d. 26 Sep 1853, Plattsburg, Clinton County, New York; bur. Schuyler Falls, Clinton County, New York (Hilyard Cemetery).
7. John HILLIARD b. 5 Jan 1768, Preston, New London County, Connecticut.

David Hillard of Little Compton, R.I., and wife Susanna to Jonathan Hillard of Stonington. Feb. 4, 1718. Land beginning at the sw corner of Moses Palmer, his land, and thence running in a direct line southwest and by west near to a great rock on ye left side of a brook, and a walnut tree standing on ye rock, and a rock marked thus I on ye side of it, and marked D on ye north side, from thence bounded by the brook on the east side until it comes to land laid out to Joshue Holmes, ye northeast corner of it being a pine tree, and so by said land to land laid out to Moses Palmer, and by said palmer to ye tree first mentioned. Witnessed by JohnMcDowell and William Holdridge. Stonington Land Records, Volume 3, page 239

David Hilliard from Jonathan Hilliard (cooper) with the consent of his wife Abigail, the one half he received in Little Compton from his father by will for four hundred pounds ---------------. Signed by Jonathan Hilliard and witnessed by William Holdred, John MacDowel and John Yeoman on 4 February 1717/8. Bristol County Land Records, Book 11, page 431

John Smith of Groton, yeoman, for 120 pounds, to Jonathan Hillard --quit claim to a certain tract of land and buildings situated in the town of Stonington bounded in a mortgage deed to me by said Jonathan Hillard which deed bears date May 21, 1728, and do by these presents surrender and yield unto said Jonathan Hillard the full and peacefull possession all such real estate as in above said tract. Witnessed by D. Elderige and Lional Udall.
Stonington Land Records, Vol. 4, page 214. May 16, 1730

On 28 JAN 1744/1745,Isaac, son of Jonathan, deceased, selected William Hilliard of Stonington as his guardian.

On 21 MAR 1742/1743, John, son of Jonathan, selected Ephraim Kingsbury of Norwich. Barbour Manuscript

1. David HILLARD b. 3 Sep 1718, Stonington, New London County, Connecticut.
2. Azariah HILLARD b. 30 Nov 1719, Stonington, New London County, Connecticut; d. Bef 1724, Stonington, New London County, Connecticut.
3. Joanna HILLARD b. 24 May 1722, Stonington, New London County, Connecticut.
4. Azariah HILLARD b. 16 Jun 1724, Stonington, New London County, Connecticut.
5. Isaac HILLARD b. 2 Oct 1726, Stonington, New London County, Connecticut.
6. 4. John HILLARD b. 12 Mar 1728/1729, Stonington, New London County, Connecticut; d. 1793, Danby, Rutland County, Vermont.
7. Ambrose HILLARD b. 6 Feb 1730/1731, Stonington, New London County, Connecticut; d. 24 Jan 1731/1732, Stonington, New London County, Connecticut.