4 bars checked · updated 18 September 2026
The short answer
In Massachusetts the oldest claim and the earliest record are the same house: Longfellow's Wayside Inn at Sudbury, where David How was licensed to keep a tavern in 1716. Neither its trade nor its fabric is continuous — the inn closed from 1861 to 1897, and the building was gutted by fire in December 1955 and reconstructed with Ford Foundation money. Warren Tavern in Charlestown, built about 1780, has the older surviving colonial frame but lapsed as a tavern from around 1813 until 1972.
Massachusetts has the best colonial licensing records in this collection, because New England towns kept them. A selectmen's vote or a county court entry will often give a name, a house and a year, which is why the state's contenders carry precise dates rather than vague centuries. What Massachusetts does not have is continuity. The Wayside Inn spent thirty-six years out of the trade in the nineteenth century and then burned; Warren Tavern was a bakery, a club and a warehouse for a century and a half before restoration in the early 1970s; the Bell in Hand has moved premises at least three times and closed during prohibition; and the Union Oyster House, which has never shut since 1826, opened as an oyster shop and put its bar room in only in 1983. The result is a state where you can name the day a tavern was licensed and still not be able to say that anybody has been drinking there ever since. That gap is the whole subject of this site, and Massachusetts illustrates it more cleanly than anywhere else in America.
Longfellow’s Wayside Inn is a rambling red coaching inn on the old Boston Post Road, licensed to the How family in 1716 and still taking guests. Its literary fame is genuinely consequential: Longfellow’s 1863 collection turned a working roadhouse into a national monument, and Henry Ford bought and restored it sixty years later. Much of the present fabric is post-1955, because the fire that December gutted the building, and the reconstruction is careful rather than original. The historic bar room, the dining rooms and the rooms upstairs are all still in use.
Warren Tavern is the better building and the more interesting survival: weatherboard on a Charlestown corner, low beams, a Masonic history signed off by Paul Revere, a visit from Washington in 1789, and a rescue from demolition around 1970. The Bell in Hand in the Blackstone Block is the busiest, named for the hand bell its founder carried as town crier, and it makes the boldest continuity claim on the thinnest evidence. Round the corner from it, the Union Oyster House has fed people without a break since October 1826 in a building of about 1716, which is why the National Park Service calls it the country’s oldest restaurant — and why it is not in our ranking, since what opened in 1826 was an oyster shop and the bar room came in 1983. All three are minutes from the Freedom Trail. For the wider argument see what is the oldest bar in America and the oldest bars in the USA.
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Sudbury, Massachusetts
The National Register nomination is the record behind the claim: Samuel Howe, a carpenter, is believed to have begun the inn about 1700 with two rooms, a taproom below and a guest chamber above, and his son David was granted a licence for innkeeping by the Concord Court in 1716, keeping Howe's Tavern until 1746. Ezekial Howe, landlord from 1746, renamed it the Red Horse and led two companies of Sudbury militia to
Boston, Massachusetts
Eliphelet Newell built the tavern soon after the British burned Charlestown, and King Solomon's Lodge, whose charter Paul Revere signed, met here in 1783-84. Tavern use lapsed about 1813 and the building served as a bakery, a club and a warehouse; the Boston Redevelopment Authority restored it in 1971 and it reopened as a tavern in 1972, so the trade is not continuous even though the house is. The tavern itself
Boston, Massachusetts
The 1795 is the tavern's own, printed at the head of its website as 'America's Oldest Tavern: First Pour 1795' and cited here from a 2019 copy because the live site refuses readers it does not recognise. Wikipedia notes the foundation by town crier Jimmy Wilson rests on tradition. The business has moved several times to reach 45 Union Street and it stopped trading during Prohibition, so 'oldest continuously
Boston, Massachusetts
The 1826 is documented and is not a drinking house, which is why the grade here is C and the ranking leaves the house out. The nomination that made this a National Historic Landmark on 27 May 2003 sets out the sequence plainly: a dwelling in the early 1700s, a specialty store from 1742, and a restaurant from 1826, when Hawes Atwood opened his oyster house on the ground floor on 7 October. The house's own wording is
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