Situated in the heart of Lahaina, the 34-room Pioneer Inn was a piece of history built in 1901 by George Alan Freeland, a British adventurer who followed his star to Maui and started a family with a Native Hawaiian woman. The hotel became the linchpin of a modest business empire that eventually included a saloon, a liquor wholesale operation and movie houses in plantation camps.

Now the Pioneer Inn, owned today by Mr. Freeland’s grandson, figures among the architectural gems obliterated by the wildfire that swept through Lahaina, wiping out not just buildings but sites imbued with historical and cultural significance to many people in Hawaii.

“The Pioneer Inn was the place where crusty old sailor types used to hang out,” said Theo Morrison, the executive director of the Lahaina Restoration Foundation, which manages more than a dozen historic sites in the town. “But it was also where we would hold our Rotary meetings before the fire. It was part of Lahaina’s daily life for well over a century,” she said. “And now it’s gone.”

Indeed, while the community of about 12,700 people is known as a vacation destination for many visitors, for many locals it is simply their home — a place where the presence of some families, especially Native Hawaiians, harken back centuries to an era long before the tourists arrived, and well before the United States annexed Hawaii in the 1890s.

The losses in Lahaina from the fire now include the historic Baldwin Home, which houses the restoration foundation’s main office and was considered the oldest house still standing on the island of Maui. It was built between 1834-35 by the Rev. Ephraim Spaulding, a missionary from Massachusetts who prized its proximity to the waters where whaling ships once anchored.

The home contained the wooden rocking chairs that the family of the Rev. Dwight Baldwin had shipped all the way from their East Coast home in the 1830s when he took over the compound, their son’s antique shell collection and the medical instruments that Dr. Baldwin, a missionary and physician, had used to vaccinate much of Maui against smallpox.

Unlike others in Lahaina whose families in the area stretch back generations, Ms. Morrison, 75, from Berkeley, Calif., happened upon the town while sailing around the Hawaiian islands in 1975. She said her mind was made up when she set out on foot around the town, once known as a vacation spot for Mark Twain and as a gathering point for whalers, now featuring art galleries and restaurants. “I walked down Front Street,” she said, “and decided this was my place.”

In the wake of the fire on Thursday, the sense of loss — of history, of community, of friends and family — was coming achingly into focus for many of those who had long lived there.

Kiha Kaina, 46, a Native Hawaiian tattoo artist who grew up in Lahaina, was one of the few people allowed into town to drop off water and supplies for residents stranded there.

Family and friends had sent him videos of the fires, but none prepared him for the heartbreak he felt seeing the destruction in person: the smoke still rising from the flattened homes, the firefighters who looked like “zombies,” the downed power lines, the charred cars.

Mr. Kaina said he personally knew more than 10 people who were still missing, including his biological father and one of his kickboxing students. “Everything that you could think of that meant a lot to this town were just gone,” he said.

Lee Anne Wong, the executive chef at Papa’aina, the restaurant in the Pioneer Inn, said one employee was still unaccounted for, and she said she expected that the death toll would climb significantly because there were so many old wooden buildings around town, making it a “tinderbox.”

“It happened very, very fast,” said Ms. Wong, who moved to Hawaii a decade ago from New York City, where she had been the executive chef of the French Culinary Institute. “A lot of employees are in shelters in the same set of clothes, and they are just thinking about their next meal.”

She added: “I’m thankful for the people who made it out alive, but an entire town has burned down.”

Originally called Lā-hainā — which roughly translates as “cruel sun” in the Hawaiian language, a nod to the area’s dry, sunny climate — the town was known before the fire as a place where one could reflect on centuries of Hawaiian history simply by walking around.

“Many people don’t understand that Hawaiians have been in these islands for nearly 2,000 years,” said Ronald Williams, an archivist with the Hawaii State Archives who has researched Lahaina for decades. He likened the city to global capitals like Mexico City, where different layers of history are visible. Walking around Lahaina before the fire, Mr. Williams said, was a chance to listen to “voices from the 18th century that are clearly wanting their stories to be told today.”

The Front Street area includes, near Shaw Street, the Moku’ula archaeological site that once served as the Hawaiian kingdom’s capital; Prison Street, which served as the monarchy’s prison; buildings dating back to the whaling, missionary and plantation eras of Hawaiian history; and the trinket shops and retail outlets now symbolizing tourism’s importance in Hawaii.

“To locals, it’s a very touristy spot, but we embraced it,” said Jared Hedani, 37, a grant specialist of Japanese-Filipino ancestry and who has lived on Maui nearly his whole life.

Yes, many of Lahaina’s old wooden storefronts had gone from housing fish markets to high-end tourist spots like Tommy Bahama and Cheeseburger in Paradise, but the town maintained its charms. Mr. Hedani said the fabled beach areas on Oahu that Hawaii is best known for held nothing on Lahaina. “To me, Front Street is better than Waikiki,” he said.

Mr. Kaina, the tattoo artist, said he never took for granted the town’s stunning sunsets, temperate climes and pristine beaches. He recalls fondly nights spent with his family feasting on fresh-caught fish and working alongside laborers from around the world in the nearby pineapple fields.

“You’re sitting there, and you see the islands in front of you and the water, and the whales are jumping, and even as a local, I’m like ‘Bro, is this real?’” he said. “The sunset looks fake every time I see it.”

For some Kānaka Maoli, as many Native Hawaiians call themselves, Lahaina was particularly notable as the place where Kamehameha the Great, the monarch who united all the Hawaiian islands, established his kingdom’s seat at the dawn of the 19th century.

Kaniela Ing, a former state legislator and Native Hawaiian organizer, said several buildings in town traced the story of Hawaii’s industrial and capitalist development, evolving from the era of the Hawaiian kingdom to the sugar and pineapple plantations and finally, in more recent years, tourism and luxury hotels.

Longtime residents, he said, have had to endure the effects of both displacement and climate change.

“The fire, to me, is a symbol of the terminal point of that trajectory, like where it all ends up if you keep down this road of extraction,” said Mr. Ing, who is the national director of the Green New Deal Network, which seeks a climate-conscious reconfiguration of government programs.

Still, until the fire hit, Lahaina was mainly known for its mellow vibe; small locally owned galleries still thrived among chain surf shops and jewelry stores. Mr. Hedani said he and his friends would stroll Front Street during nights out on the town and play “Spot the Local” — a difficult challenge among the hordes of visitors.

And whenever he passed the Kishi Building on the waterfront thoroughfare, he felt a rush seeing the historic name. It had once been his family’s fish market, opening in 1903 and closing in the mid-1970s.

“I’d always pass by there and I’d look up at the name and feel a little sense of pride,” he said.

It appeared to have been one of the first on Front Street to burn.

Mr. Hedani said he worries that buildings will not be rebuilt in the same style, that the owners of small galleries and eateries won’t be able to afford to rebuild, and there will only be room for businesses that cater to wealthy clientele, like in parts of Waikiki, where designer temples lure foreign shoppers.

“What happens when you take away the most important street on Maui?” he said.

Amy Qin, David W. Chen and Mitch Smith contributed reporting.