Vintage Rye: Rye’s Swinging Night Life

“You’re from Rye, New York? Wow, I used to go there to drink when I was young.” 

Published May 11, 2016 2:13 PM
5 min read


“You’re from Rye, New York? Wow, I used to go there to drink when I was young.” 

By Karen T. Butler


“You’re from Rye, New York? Wow, I used to go there to drink when I was young.” That was true for many. Of course, one would only say that if they have graced this planet for more than a half a century. 


People came from miles around to Rye’s legendary “watering holes.” At one time, New York State’s legal drinking age was 18 and the bars stayed open till 3, and if one knew the right people the fun continued until 5 or 6 in the morning.


There also was a time when the sidewalks on Purchase Street literally “rolled up” at 6 in the evening. The Rye Liquor Store and Butler Bros. were the exception, closing at 9:30.


On Sunday, Rye’s village truly looked like a ghost town, almost everything closed. That was largely due to New York’s “blue laws,” dating back to 1695. “Be it therefore enacted that there shall be no traveling…working, shooting, fishing, sporting, playing, horseracing, hunting or frequenting of tippling houses or the use of any unlawful exercises…on the Lord’s Day.” Much of this was done to promote a day of worship. Over time the “blue laws” were slowly lifted but even in the late ’60s New York’s supermarkets were closed on Sunday, only mom-and-pop delis and grocery stores were allowed to stay open. That may be difficult to envision when the exact opposite is true today with evenings and Sundays likely to be the busiest time for Rye’s downtown.


At the opposite end of the moral spectrum during this earlier period, Rye had the fame of being a swinging, late-night place. A large part of this was the result, which included the entire State of New York, of a lower drinking age and late hours for pubs and restaurants.


So there was plenty of demand for the swinging nightlife in Rye. Cars brimming with party-loving folks, by the hundreds and hundreds, came over the border into New York State, mostly on weekends. Rye did not have a lock on this crowd and wasn’t the only place with a swinging nightlife. All the border towns in Westchester had their establishments: The Border Bar, Vahsen’s, The Whiteway in Port Chester; Purchase, pre-SUNY, housed The Hilltop, The Cobblestone, and the joint of all joints, The Valley Tavern, so dark and dingy one could barely find one’s way to the powder room.


Rye’s nightlife was a thriving mini-industry. There was the Little Club, formerly Buggies, a hole-in-the-wall known for its jazz music. (Today it is called The Pub.) There was The Paddock (now Rye Grill), The Coachman, Five Points (Kelly’s), The Stagshead, The Dugout (now The Town Dock), The Jungle Club, and the list goes on.


One of Rye’s most raucous locales was the Colonial Club on Purchase Street, where Fogama’s is today. Early in the evening it was a great place for fine dining served by Peter, Rob, and their professional staff. It had a romantic atmosphere, gourmet food, and impeccable service.


If you were a night owl, it was the place to frequent. Entertainment followed later in the evening, mostly on the weekends, The crowd slowly drifted upstairs to the second floor, perfect for a cabaret, intimate and cozy, with its long well-seasoned mahogany bar, smaller cocktail tables, and Bentwood chairs. The lights were dim; the background music soft and romantic. The jam-packed crowd sat patiently sipping their cocktails, inhaling their favorite cigarettes in the smoked-filled room, talking softly waiting for the lights to dim. The atmosphere had a hushed but energized anticipation of things to come.


Suddenly, the spotlight shone on Roger Intercasso, who earlier in the evening was a dinner waiter, dressed in full peacock attire on a swing that hung over the bar. For his opening number, he sang “I Am Only a Bird in a Gilded Cage” to a crescendo of hoots, hollers, and screaming laughter followed by a roaring burst of applause when the number ended. His other showstoppers were Broadway hits: “Send In the Clowns: Maybe Next Year” from “Funny Girl,” “Cabaret,” and many more.


By day, Roger, was one of the best short-order cooks in the business at Rye Sweet Shoppe (across from where Starbucks is today). He entertained his clientele as he worked, with humorous and sometimes risqué banter.


“What do you want for lunch?” Roger would ask as he made sandwiches or fried eggs. Without a pause, he’d pass them to the proprietors, Dave and Millie Silverman, who served the customers with a smile and pleasant chatter. No more than a 25-foot storefront, the Shoppe was small by standards. On the left as one entered was a long counter with stationary but swiveling stools covered in red vinyl held in place by a chrome band. Rye folks sat at the counter and mid-day they were at least two-deep waiting for a good meal and a chuckle from Roger. Years later, he served lunch at the Woolworth’s counter up the block on Purchase Street.


In the 1970s a group of Rye fellows purchased Pelley’s, a longtime troubled restaurant on the corner of Milton Road and Oakland Beach Avenue. The basement door siding on Oakland Beach was where illegal deliveries of “hooch” were made during Prohibition. The group named the new spot The White Elephant for its eclectic history. (La Panetière has brightened that corner for close to 30 years.)


After dining or for a nightcap on the way home from one of Rye’s clubs or a party, the regulars would climb the stairs to The Top of the Elephant, a cozy room one flight up from the restaurant. It quickly became a Rye hit, drawing from all around the area, including New York City. 


The catalyst that drew the crowd was Dave Sayer, New York ad executive by day, and a superb piano player on Friday and Saturday evenings — Rye’s own Michael Feinstein. Dave had a collection of songs all in his head. Regulars who were there to sing gave Dave the thumbs up as they came through the door, indicating they were in full voice and ready to perform. Knowing their repertoire, Dave would throw himself into their selections, all without sheet music…all by ear. Roger, from the Colonial Club, and his partner, John, were there without fail.


Roger loved to sing, but at times could be a temperamental thespian. If he and John had a spat, John, a baritone with an operatic style, would perform a heart-rending rendition of “This Is My Beloved” to make amends.


Even Broadway would be hard-pressed to hold a candle to the music, laughter, and talent that filled Rye’s wonderful late-night establishments.



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