The Two Beach Walk

This tour offers self guided audio

We love a good stroll on the beach. Enjoy the sea breeze, take in the surroundings and follow along while you uncover some of the town’s remarkable history, including tales of witchcraft, markers of the Revolutionary War and impressive recovery efforts from hurricane Sandy.

Starting & Finishing Point: Parking Lot behind Sullivan Independence Hall - Sullivan Independence Hall is down the driveway from Fairfield’s Old Town Hall.

Address: 725 Old Post Road, Fairfield, CT 06824

Distance: 2.7 Miles

Surface: Flat terrain, mostly on sidewalks and beaches

Elevation Gain: Negligible

Listen While Touring:

Sullivan independence hall | fairfield museum | beach rd

The marshy area on the right side of the driveway used to be a pond where, in the 1600s, women accused of witchcraft were subjected to a water dunking test. If she floated, she failed. If she sank, the accused was innocent.

When the British burned 200+ buildings to punish Fairfield for its rebelliousness in 1779, they spared three homes on the East side of Beach Rd. Only 5 houses survived the burning of Fairfield by British troops on July 7 & 8 1779. Those houses, which are private homes today, are on Beach Road. They may have survived because they were used as billets for British officers during the brief occupation - not because the owner were British loyalists. These homes were said to have billeted British troops. Some think these homes were spared because the owners were Tories. There could be some truth in both stories.

Old burying ground cemetery - Revolutionary War heroes buried

The cemetery is at the South end of the Historic District.

Caleb Brewster (1747 – 1827), a member of George Washington’s Culper spy ring is buried here. Caleb reported to Major Benjamin Tallmadge, an aide to General Washington, and carried messages across Long Island Sound between Tallmadge and the Culper ring's spies on Long Island and in New York City. Caleb Brewster and the Culper spy ring are immortalized in “Turn,” a TV series available through streaming services.

• Gold Selleck Silliman – General in the Colonial army kidnapped by British loyalists in 1779 and held for a year in Long Island before being freed by a prisoner exchange.

• Isaac Jarvis - commanded the fort protecting Black Rock Harbor (now part of Bridgeport) from naval attack. A rough outline of the fort’s foundation can be seen in the water at low tide from St. Mary’s by the Sea at the East end of Black Rock Harbor, which was part of Fairfield at that time.

• Samuel Smedley – Captain of the Defense, a small Patriot frigate which captured a dozen British “prizes.” Sam Smedley eventually was captured by the British, escaped from the infamous Mill Prison in England then returned to Fairfield and fought the British when they raided in July 1779.

There were few homes between the cemetery and Long Island Sound until about 100 years ago.

Roger Sherman School

The Roger Sherman School, which is one of the top public elementary schools in Connecticut is at the end of East Paulding. Roger Sherman, lawyer and politician, was one of six men (no women) who signed the Declaration of Independence AND the Constitution. Can you name the other five? See answer below.

JENNINGS BEACH

Before you reach the Jennings Beach parking attendant shack at the end of S. Benson, cut through the parking lot on your left to Jennings Beach.

As you walk through the lot to the beach, South Benson marina and Ash Creek are on your left. St. Mary’s by the Sea, which is part of City of Bridgeport, is on the other side of Ash Creek. Battery Point, at the tip of St. Mary’s by the Sea, overlooks Jennings Beach and the entrance to Black Rock Harbor. You will get a better look at Black Rock Harbor as you walk down the beach. Battery Point was the location of a Connecticut artillery battery which kept the British out of Black Rock Harbor and Ash Creek during the Revolutionary War.

FAIRFIELD BEACH CLUB

As you walk West on the beach, after the lifeguard chairs, the first low, grey building is the Fairfield Beach Club, which is private followed by three private homes. It’s OK to walk on the beach in front of private property as long as you walk between the water’s edge and the high tide line. The next grey building is the Penfield Pavilion, a town facility used for concerts, weddings, and other events.

PENFIELD PAVILION

Penfield Rd starts across the street from the entrance to Penfield Pavilion. Walk North on Penfield Rd.

Fairfield’s Beach Area was hard hit by Hurricane Sandy in 2012. The flood water reached 11 ft. above mean-high tide. Homes south of Quincy st. were flooded above the ground floor level because the elevation in this low lying area is only 6 or 7 feet. You will notice new homes, constructed after Sandy, have elevated first floors and flood-protected ground floors.