Since 2026 marks the 250th anniversary of the founding of our country, I felt it would be appropriate to share some Smithtown history that ties into the 250th.

Shortly after the signing of the Declaration of Independence, a battle with the British army ensued. In August of 1776, solders from the revolutionary army fought the British in what was known as THE BATTLE OF LONG ISLAND.

Since the Dutch were forced out by the English in 1664 and New Amsterdam became New York, the port of NYC was a key logistical point to control. Washington’s army quickly lost the battle and thus began the occupation of Long Island by the British army.

While much of Long Island was sparsely populated during the revolution, it was also a key resource for Washington’s army to gain intelligence on the British and the Culper Spy Ring was formed nearby Smithtown and many of the roads in Smithtown are considered part of Washington’s Spy Trail.

Long Island was one of the last places for the British to leave after the war was won and, in fact, the occupation lasted until 1783.

Smithtown also had a couple of geographical features that made it a significant point on the north shore of Long Island.

The Nissequogue River forced travelers both east and west of Head of the River to funnel down to Jericho Turnpike from North Country Road. This meant passing through Smithtown was almost inevitable.

A second feature of Smithtown that was significant was the distance from the hub of NYC. Smithtown was one long day’s wagon or horse ride from NYC and a perfect place to stop for the night to rest yourself and your animals. This is why many inns and taverns popped up to fill the need.

The great grandson of the town founder saw this as an opportunity.

Epenetus Smith was born January 11, 1724. In about 1740, he purchased a small, saltbox style building that stood on the north side of the intersection of Hauppauge Road and East Main Street. This was a very good location for traffic as it was very close to the intersection of Main Street and North Country Road, and it was directly across from the major road heading south out of Smithtown.

The tavern he bought was built around 1690 but there are no records as to who built the original building. The history I have always heard was that Epenetus was seventeen when he bought the tavern, but that doesn’t quite match with the 1740 date, hence “around.”

Epenetus reportedly tripled the size of the building to add sleeping quarters. This extension was added to the east side of the original building and was also in the saltbox style. There are no pictures of the original extension as photography didn’t come along for another hundred years.

In 1772, the tavern became a stop on a stagecoach route that ran from Brooklyn to Sag Harbor. Business was good.

Approximately 35 years into his proprietorship of the tavern, the country declared its independence from England and the aforementioned Battle of Long Island took place, then the subsequent occupation.

Epenetus’ tavern apparently seemed to be an ideal location for occupation, and the British Solders settled into the tavern and took every advantage of what Epenetus had worked to create.

Epenedus was not a loyalist and was convinced that the revolution would be won by the colonialists.

Likewise, the British were convinced that they would win and continued to steal Epenitus blind, even stealing the boards off his barn behind the tavern.

Epenetus was a good businessman and kept records. He, in fact, kept a ledger of all the items the British pilfered, along with a conservative value of them.

This ledger is one of the prize possessions of the Smithtown Historical Society and will be on display at the Smithtown Library’s Smithtown Building during the semiquincentennial.  

Below is a teaser of the ledger.

In the end, both Epenetus and the British were disappointed.

Epenetus died in August of 1803, and his son Epenetus II continued to operate the tavern.

The tavern eventually passed from Smith hands and was operated as the Israel Whitman Tavern. It is believed that this is when the saltbox extension was enlarged further to add the third story attic and the colonial roofline.

This configuration is when we can find the first photographs of the tavern on its original foundation, across from what is now Singer Lane.

The tavern passed to David J. Ely and then was purchased in the early 1900’s by John S. Huntting with the intention to raise it for a home. (As an aside, Huntting built the store just west of this location that “old timers” know as Colonial Furniture. The right side of that store was Smithtown’s first A&P.)

Huntting was the founding president of THE NATIONAL BANK OF SMITHTOWN BRANCH (later The Bank of Smithtown). The original bank building still stands between where the tavern original stood and the Colonial Furniture building.

Back to the tavern history and its impending destruction... In what is now the two Smithtown shopping centers – from Singer Lane to Lawrence Avenue, and all the way back to Miller’s Pond – was the Miller Farm. At the time Huntting bought the tavern, Mrs. Charles Duncan Miller resided at the farm and acquired the tavern to save the historic structure.

In 1911, Mrs. Miller had the tavern jacked up and moved south along Hauppauge Road (RT 111) to just south of where the current Smithtown Post Office. This was at the front of the Ludder Florist property (now Uncle Giuseppe's Marketplace shopping center). The south side of Main Street, at this time, was primarily large open fields; the picture below shows as the building stood in the second location on the east side of Hauppauge Road. It also shows the third floor attic dormers and a wrap-around porch on the original section. George Ludder (still in town today) remembers playing in the footings of the second location as a child on the florist property after it was moved the third time.

The tavern stayed in this location until the winter of 1928-29 when it was jacked up again and “translated” across Hauppauge Road to the west side. I say “translated” as it was moved such that the rear of the building now faced Hauppauge Road, rather than the front. This put the long roof side of the saltbox section facing the road.

 

This location on the west side of Hauppauge Road with the relatively long driveway making a circle near the doorway resulted in the tavern having an elegant look. This was where the office building at 50 Hauppauge Road is today, just to the left of the Village Hall for the Village of the Branch.

 

The peaked roof extension off the old section was a kitchen. It was bought by Dorothy Payne and opened as the OLDE TAVERN HOUSE restaurant in 1963. It seemed like a great use for this historic building and in keeping with Epenetus’ vision. Unfortunately for the tavern, the state decided that the traffic patterns associated with RT 111, East Main Street, and North Country Road had gotten out of hand. This was an understatement. The intersections frequently gridlocked, and the weak narrow bridge just north of Mount Pleasant Road was not capable of supporting large trucks. The twists and turns through the woods resulted in accidents on a regular basis. The solution, in 1966, was to straighten RT 111 starting just south of Mount Pleasant Road and make it connect the North Country Road directly.

This all sounded like the right thing to do, but the implementation meant the elegant entry and long drive to the tavern would be truncated to leave the building almost directly on Hauppauge Road. The restaurant kitchen also needed to be brought up to new health codes – the story I heard was that the town of Smithtown was not exactly fast-tracking this process. The result was that the OLDE TAVERN HOUSE closed after 1969.

The building sat fallow for a few years until it was marked for destruction again to make way for the office building there today.

The building was acquired by the Smithtown Branch Preservation Society that also owned the Judge John Lawrence Smith Homestead along the historic corridor on East Main Street. In January of 1972, the building was jacked up a third time and moved to its fourth location adjacent to the homestead.

In keeping with the trials and tribulations of one of the oldest buildings in the incorporated Village of the Branch, it rained long and hard for the move, and the building became stuck in the mud.

It took an additional day to maneuver the tavern onto its new foundation.

About ten years after the tavern was placed in its fourth location (no more than a quarter mile from where it was first built), the Smithtown Branch Preservation Society merged into the Smithtown Historical Society. This resulted in a campus of more than twenty acres dedicated to the preservation and education of town history and life.