"They're very appreciative to get in here, something they've all been waiting anxiously for," Maui Emergency Management Agency interim administrator Darryl Oliveira told reporters outside what has become known as the "burn zone".
"People who haven't been here since the fire are taken aback by the amount of and extent of the destruction."
While some people were able to return to their properties to evaluate the damage in the days following the August 8 wildfire, the burned area has since been off-limits to all but authorised workers.
Authorities opened a small part of it on Monday to allow residents in for supervised visits from 8am to 4pm, with about two dozen vehicles carrying residents entering the area by midday.
The prospect of returning has stirred strong emotions in residents who fled in vehicles or on foot as wind-whipped flames raced across Lahaina, the historic capital of the former Hawaiian kingdom, and overcame people stuck in traffic trying to escape.
The wildfire killed at least 97 people and destroyed more than 2000 buildings, most of them homes.
Some survivors jumped over a sea wall and sheltered in the waves as hot black smoke blotted out the sun.
Officials urged returning residents not to sift through the ashes for fear of raising toxic dust.
The first area to be cleared for re-entry was a zone of about two dozen parcels in the northern part of Lahaina.
From a National Guard blockade near the burn zone, Jes Claydon has been able to see the ruins of the rental home where she lived for 13 years and raised three children.
Little remains recognisable beyond the jars of sea glass that stood outside the front door.
Claydon hoped to collect those jars and any other mementos she might find.
"I want the freedom to just be there and absorb what happened," she said.
"Whatever I might find, even if it's just those jars of sea glass, I'm looking forward to taking it.
"It's a piece of home."
Claydon's home was a single-storey house painted a reddish-tan, similar to the red dirt in Lahaina.
A few of the walls are still standing and some green lawn remains, she said.
Those returning were given water, shade, washing stations, portable toilets, medical and mental health care, and transportation assistance if needed.
Non-profit groups also offered personal protective equipment, including masks and coveralls.
Officials say ash could contain asbestos, lead, arsenic or other toxins.
Most journalists were confined to an area where they could not see people visiting their properties.
Oliveira said officials wanted to ensure residents had space and privacy to reflect or grieve.
A team of more than two dozen people from Samaritan's Purse, a non-denominational Christian ministry, was on hand to help residents sort through what was left of their homes, said Todd Taylor, who works with the organisation.
"It's like losing a loved one," he said.
"That's exactly what these folks are going through."
