1661
John How, one the first settlers in the Massachusetts Bay Colony, and son of John How of Warwickshire, England, is granted a license for a house of public entertainment (“pub”) in Marlborough, beginning a multi-generation tradition of How family innkeepers. His son Samuel, among other professions, continues the inn-keeping business in Marlborough.
1700
One of Samuel How’s sons, David, marries Hepzibah Death on Christmas Day.
1702
Samuel How deeds to his son, David, Lot #50 of the Sudbury New Land Grant, for him to build a home for his new family. A map of the land, dated 1702, depicts it without any dwellings.
1707
The first written record of a building on Lot #50, a map dated 1707, shows one small dwelling; David How’s first homestead (today represented by the Old Bar and the chamber above). The “summer beam” in today’s Old Bar is original to How’s first home.
1716
Four Sudbury selectmen petition the “Court of the Sessions at Concord” and grant David How permission to “keep a hous of entertainment for travelers.” It is theorized at this time that David How doubled the size of his original two-room home.
1748
First year Ezekiel How (son of David) listed as the holder of the inn-keeping license. An undated document shows that Ezekiel charged “Lodging 4 pence each; A good dinner 20 pence; Common dinner 12 pence; Best Supper and Breakfast 15 pence each.”
1759
David How, dies at age 85. his son Ezekial inherits the Inn.
1750-1760
Lumber receipts indicate that Ezekiel makes significant improvements to the Inn building (eight total rooms with new gambrel roof).
1775
On April 19th, Lieutenant Colonel Ezekiel How leads the Sudbury Company of Militia and Minute to Concord to confront British regulars in the first military engagement of the American Revolution.
General George Washington passes How’s Tavern as he rides to Cambridge to take command of the Continental forces (a tablet in front of the Inn attests to his passing the tavern).
1784
The Marquis de Lafayette, on his third visit to America, travels the Boston Post Road on his way from Albany to Boston.
1785
Lumber receipts indicate that the “New Kitchen and chamber above” were added to the Inn (today’s Tap Room and Ballroom above).
1789
George Washington again passes How’s Tavern. His diary mentions stops in Marlborough and an overnight stay at a tavern in Weston.
1796
Ezekiel How dies at age 76, and son Adam takes over as innkeeper. Adam attaches a small barn to the east, converting it to a large kitchen with chambers above (the Old Kitchen and rooms 9 and 10 above).
1808
Isaiah Thomas, publisher of the Massachusetts Spy, writes in his journal “Very cold. Very bad traveling. Snow light. Broke the Sleigh a few rods from Howe’s...in Sudbury. Tarried at Howe’s from 11 o’clock this forenoon.”
1819
Archives records contain a handwritten ticket reading “Admit the bearer to A.How’s Hall [today’s Ballroom] in Sudbury on Wednesday Evening, Jan. 27, 1819.”
1824-1826
Lafayette again passes How’s Tavern as he travels the Boston Post Road and makes his final tour of the US.
1828
Abolitionist writer (and author of Over the River and Through the Woods) Lydia Maria Francis-Child visits How's Tavern, and later recalls “The dinner was plain and old fashioned, like all else around us, but everything was delicious.”
1830
Tradition states Lyman How begins his tenure as innkeeper.
1835
Adeline Lunt, wife of Boston editor and journalist George Lunt, visits the Inn and later recounts “[The How(e) family] were indeed a pleasing representative of old fashioned New England respectability and prosperity in its best sense combined with domestic happiness and virtue.”
1840
Adam Howe dies at age 77.
1842
Jerusha Howe, the "Belle of Sudbury" and daughter of Adam Howe and sister of Lyman, who is said to have entertained visitors by playing the pianoforte in the Parlor, dies unmarried at age 45.
1853
On May 22, Henry David Thoreau writes in his Journal “Left our horse at How's Tavern. The oldest date on the sign is ‘D.H. 1716.’”
1861
The last of the How innkeepers, Lyman, dies at age 60 having never married and the Inn passes to relatives who no longer wish to operate the tavern. In November of that year, an auction was held to settle Lyman’s debts, totaling over $6,600––many Howe heirlooms were purchased.