Pear Tree Point Road was originally constructed in 1867, and in 1908, H. G. Fleitman gave some of his land to the town to straighten the road. This bit of land was later used for a picnic area, according to the Corbin Document.

Pear Tree Point was not always pristine, according to an essay written by the late Conrad Frederick Wegner, who served on the Board of Selectmen in the 1920's. "For years we would pile the debris collected during the spring cleanup down behind the bathhouses at Pear Tree Beach. After a while people complained about this eyesore," Wegner wrote in his essay, which was published in Edmund F. Schmidt's book Noroton Heights: A Neighborhood for Generations.

Another essay in Schmidt's book, written by the late Tom F. Murray, who served as the Noroton Heights postmaster claimed that the police would attempt dispose of seized bottles of alcohol there during prohibition:

"I can still remember [Officers] Frank Standing and Al Brunner throwing the bottles on the big rocks down there or into the town dump behind the beach. Some folks used to hide in the bushes and would come out to get the bottles that failed to smash. They used to holler out, `What's the matter with you, can't you hit that big rock?'"

In March, 1926, the town borrowed $30,000 to improve the area, and construct shower rooms, 300 bath houses, a concession stand and other beach conveniences. The beach was then opened to the public in July of that year.

Eleven years later, Darien became the first town in Connecticut to require non-residents to pay an entrance fee to the beach. The new policy charged Darienites 25 cents to purchase a tag for their car which identified them as residents, and allowed them to ignore the fee. These days, resident are charged $35 for a pass, while day passes for non-residents cost $40.