Just before 9 a.m. on Monday, the water at the head of Three Mile Harbor was spilling onto the town docks. A few boats, girded with bumpers and floats, remained.
In Montauk, water from Fort Pond Bay was pouring into Lake Montauk. Flooding was observed in parts of downtown Montauk. The Star Island causeway was nearly overtopped by the rising water.
In Amagansett high waves were pounding the north and east-facing bayfront. Ocean beach access were closed across the South Fork, and officials were ordering all non-emergency vehicles from the roadways.
There were reports of downed trees in several locations. Fire department volunteers were reporting to scenes of fallen electrical wires.
Flooding had already closed some roads by noon Monday.
An emergency evacuation shelter had opened at East Hampton High School on Long Lane, East Hampton, staffed by the American Red Cross.
At Gann Road at Three Mile Harbor water pooled in the parking lot at Harbor Marina, where most of the boats had been hauled.
Coast Guard personnel worked to secure two of the agency's boats to the town commercial dock. Staff in orange foul weather gear hauled their bags from the back of a truck onto a third Coast Guard boat. The waters of Three Mile Harbor had risen to a level flush with the edge of the bulkhead at the dock.
Few cars were on the road in Springs, though early winds had pushed plenty of leaves across the pavement. At the end of Flaggy Hole Road, waves from the bay lapped at the pavement's dead end. Officials had taped off the Maidstone Park Road. Neighbors were using the open, high ground of the ball field there as a parking lot safe zone away from potential falling tree limbs; a line of cars was parked along the grass.
On Landing Lane, Springs, a dead end leading to the interior of Accabonac Harbor, a large fallen tree blocked the road.
The waters of the harbor had already risen to fill the yards of houses nestled along the waterfront curves of Old Stone Highway, and at the corner of Old Stone and Louse Point Road, a puddle of coastal water was growing, joining wetlands on the east side with the harbor.
Pickup trucks that ventured through that pond stopped a short stretch down the road, where flooding obscured the road for a long stretch toward the bay.
At the heart of Springs, near the Springs General Store, the normally bucolic Pussy's Pond, connected to Accabonac through a culvert under Old Stone Highway, was pushing fingers of water onto areas that were formerly dry land with benches, giving rafts of ducks a byway right to the corner of School Street.
The measures that businesses are taking to prepare for Sandy run the gamut. Randall Hemming manages Devi Kroll, a Main Street, East Hampton, women's clothing boutique surrounded by boarded-up and sandbagged storefronts. He called applying lime green and azure-blue tape to eight-foot-high store windows Sunday night a "safety precaution," as he pointed to a tree that sits outside the store's entrance. "Just in case that tree falls through a window," he said, "Glass won't be shattered all over the place." When asked about when the store would reopen, Mr. Hemming said he would "play it by ear."
The same words were used by Michelle Moliski, a manager at Rowdy Hall, a restaurant and bar tucked away in a Main Street alleyway. "We've done what we can do," she said Sunday at 8 p.m., when two diners and eight bar-goers were being served. "If people want to come in to have a beer, then by God they should be able to." Earlier Sunday she removed furniture and Halloween decorations from the restaurant patio, and she expects delays in decorating the patio for Rowdyween, its annual costume party on Wednesday.
Elizabeth Barnes, co-owner of Dockside, a restaurant in steps away from Sag Harbor Bay, also removed all tables, chairs, and umbrellas from the restaurant patio. In addition, she folded away the eatery's awning, which she said the Sag Harbor Yacht Club, where a few boats were still docked, did as well. "It has been quieter than usual," Ms. Barnes said of weekend customer traffic — six tables being served Sunday at 8 p.m. She hopes to put the furniture back outside lunchtime Thursday. "We hope to have a few more nice weekends," she said.
Ed Schuster, head bartender at the Corner Bar in Sag Harbor, which served lunch on Monday, called the prospect of remaining open for dinner, "questionable."
Nado Stipanov, a manager at Astro's Pizza in Amagansett, said the pizzeria would stay open for lunch and dinner on Monday, or until "the police come to shut us down."
On North Main Street just before East Hampton Village, spooky Halloween cobweb decorations still clung to hedges.
With reporting by Russell Drumm, Larry LaVigne II, and David E. Rattray