Leo and the Inn

Early in the twentieth century, a Middletown resident describes the sleepy town’s main thoroughfare as follows:

Along with residences that line the street today, there were numerous businesses … an ice cream
store that had a soda fountain, a blacksmith’s shop, the Middletown Movie Theatre, a restaurant,
the Middletown State Bank (now the location of Nana’s Irish Pub, formerly the The Irish Isle), and
several grocery and dry-good stores, including Herbert Rhodes Dry Goods, Parker’s Store, Doug Edmondson’s Dry Goods, and Little & Larrick Grocery Store (McCarty. TWS. Undated). 

Not a booming metropolis, but certainly not a dead one.

Not mentioned in the above list were two very obvious landmarks.  At Middletown’s single traffic light, located at the intersection of Main Street (Route 11) and First Street, stands the imposing, historic Wayside Inn.  Since 1797, the Inn, originally called Wilkenson’s Tavern, was a stagecoach stop for travelers who traversed this major north-south artery.  Just one block south of the Inn is the town’s other major landmark, The Wayside Theatre.  Despite the gap in their dates, 1797 for the Inn, and the 1960s for the Theatre, there is a close connection between these two buildings.   

In the early 1960s, neither the Inn nor the town were in a thriving state.  “If the Inn was in bad shape,” states one source,

… Middletown itself was not the picture of health.  Unemployment was a significant problem,
the only sanitation facilities were septic tanks and outhouses and the population count hadn’t
changed appreciably in decades.  The town had stopped on dead center, one resident recalls. 

It was into this rather stagnant environment that Leo Bernstein stumbled, and his action became “a sort of catalyst to community development” (Blackwell. “Wayside Inn Gives ….” TWP. 10 Apr. 1969).

Some improvements in the town were already taking place before Bernstein’s arrival on the scene. Some residents felt that these changes in the community were the result of what was taking place at the Inn.  It is not clear which came first.  Leo Bernstein “is quick to point out that these signs of future prosperity were not his doing alone.” While this may have been the case, one cannot cannot deny that, “It is apparent … [Bernstein] at least got the movement started.”  Other Middletown residents feel that his purchase of the Inn provided the stimulus for the town council to seek a grant to cover the cost for a local sewer system.  Archie J. Manuel, the mayor of Middletown at the time, says of Bernsetin, “He’s really been a big help to Middletown. I respect his knowledge of business and I respect him” (Blackwell. “Wayside Inn ….” TWP. 10 Apr. 1969). 

Some of the residents expressed their approval of Bernstein’s purchase of the Inn and his plan to revitalize it.   One report states, “Gene T. Dicks, mayor of the town, is enthusiastic about Bernstein’s work and plans” (“Small Town Catches ….” TWP. 24 Feb. 1962).  But, not everyone in Middletown felt that this purchase by an outsider had been a positive move.  Some in the community objected to Bernstein’s “interference and throwing his money around.”  Yet, even these doubters had to acknowledge that “change is always difficult” (Blackwell.  “Wayside Inn ….” 10 Apr. 1969).  

The history of the Wayside Inn is long, colorful, and well established.  No less colorful is the story of the Inn’s acquisition by the Washington DC banker/real estate magnate, Leo Bernstein.  Basically, the story states that Bernstein was returning from a business trip in one of the Carolinas and heading to his home in Washington, DC.  As he drove through Middletown, he caught sight of the Inn, turned around after passing it, went in for a meal, and ended up purchasing the property that very day! 

There are several versions to this story, along with a variety of dates, as to when this event took place.  One tells of Leo Bernstein, returning to DC after a meeting in 1959, sees the Inn, falls in love with it, and purchases it (The Shenandoah Free Press. 19 Nov. 1986).  Another recounts the event in the jargon of a town native. “A stranger with DC plates on his Cadillac drove slowly through town on Rte 11 one day in May, 1960, seemed to hesitate when he passed the Wayside Inn, turned around in a service station driveway and then pulled into the Inn’s parking lot” (Blackwell. “Wayside Inn ….” 10 Apr. 1969).  Still, a different date for this incident, from a Winchester paper states,  “[…] fifteen years ago (1961) Leo saw the inn and signed the contract ‘then and there’ ” … with the agreement with the owner Mrs. Genarro [Gertrude F. Jeannaro] to “let her have what was in it” (Burke, S. “He Came, Bought ….” WES. 20 Jan. 1976).  The records found among the Leo Bernstein papers at the Jewish Historical Society adds still more confusion.  In response to a question, the JHS archivist replied, “a Washington Post newspaper article written in the 1980s about the Inn, and a Wayside Inn newspaper called the Wayside InnQuirer, published circa 1966, both give the dates [for the purchase] as May 1961 … while an undated oral history transcript done by Leo … gives the date as 1957, quoting Bernstein as saying, ‘when I was 42!’ ” (Turman. Email, 2015).

Despite the variations in the date as to when this transaction took place, 1957, 1959, or 1961, the property records show that Bernstein purchased the Inn on June 8, 1961 (Frederick County Court House). It is the general consensus that the Inn was definitely not in perfect physical condition at the time of the purchase.  One description of the property goes so far as to say that it was “… in shambles. It had no heating system and business was terrible” (Blackwell. “Wayside Inn ….” 10 Apr. 1969).  Purchasing a property in such a state of disrepair illustrates the confidence and the vision of the buyer, and confirms Bernstein’s reputation as an entrepreneur in the world of real estate.

Bernstein’s purchase of the Wayside Inn was a monumental event for Middletown.  One headline calls the acquisition a major coup, stating, “A tiny Virginia town with an historic inn is getting a shot of private-capital adrenalin from a Washington financier.  The town is Middletown (pop. 386) and the ‘doctor’ is Leo M. Bernstein.”  The purpose of this acquisition, continues the unnamed author, was to make Middletown “a stopping-off place for tourists attracted to the Nation’s Capital and all parts of Virginia” (“Small Town Catches ….” TWP. 24 Feb. 1962).   

Another source suggests that Bernstein might have had a long-range plan when he acquired the Inn, which was “… to convert an old movie house into a theatre for summer stock” (Blackwell. “Wayside Inn ….” 10 Apr, 1969). The almost exact wording is used by another reporter, noting that Bernstein had “A plan […] to convert an old movie house into a theater for summer stock” (“Small Town Catches ….” TWP ).  

Could it have been possible that, when Bernstein passed through Middletown on his way to DC, he noticed that there were two buildings in need of attention -- a theatre and an Inn that were separated by only a single block? Driving north, he would first have passed the movie house that had been closed since 1958 before approaching the historic Inn. While driving the short distance between the two buildings, could the idea have materialized that by connecting the two, a profitable venture could be created that would be a way to increase the tourist trade in this vicinity?  One can only wonder. 

Despite the confusing accounts found in various sources, as of June 1961, the Inn was under new ownership, and an imaginative entrepreneur was about to work his magic.