Weather 
For decades, Labor Day in the Hamptons meant the crowds left, shared houses emptied and locals reclaimed their towns from chaotic summer tourists.
Known colloquially as “Tumbleweed Tuesday,” the day after Labor Day once marked a real economic and cultural cutoff between the frenetic summer season and the quiet months that followed.
But that timeline has increasingly blurred since the pandemic as second-home owners spend longer stretches in the Hamptons and remote work makes it easier to file earnings reports from a couch in Quogue.
Because of these lingering second-housers, Tumbleweed Tuesday is fading away —all while influencers who have barely unpacked their bikinis haunt Hamptons farms for ripe pumpkins, colorful foliage and meticulously curated “cozy” fall content.
When Tumbleweed Tuesday meant something
Ned Dougherty remembers just how literal “Tumbleweed Tuesday” once was.
The 79-year-old, who grew up in Pennsylvania, has lived in Westhampton since 1967 and later owned the popular Main Street hotspot Club Marakesh.
Dougherty told The Post that on the Tuesday after Labor Day in 1971, he stood in the middle of a car-free street in downtown Westhampton, watching privet branches blow down the street, resembling the tumbleweeds of abandoned mining hubs in the Wild West.
“We’re talking history when we’re talking Tumbleweed Tuesday,” Dougherty told The Post. “It became a ghost town for nine months.”
But more than five decades later, Dougherty says Tumbleweed Tuesday has lost much of its meaning.
Business now stretches through October and into November. More families spend longer chunks of time out East, and thanks to influencers seeking country-core content, the region has become a hotbed for TikTok shoots and fashion campaigns.
“Tumbleweed Tuesday no longer has meaning because the season doesn’t end,” Dougherty said. “I can only assume it’s become a marketing term because everyone now has some event.”
Celebrated and dreaded
For locals, Tumbleweed Tuesday became an unofficial reward for surviving the summer rush — and veteran Hamptons restaurateur Mark Smith still understands the appeal.
“Business-wise, I hate to see summer end since that’s our revenue. But personally, it’s nice when crowds and traffic ease,” said Smith, who has spent roughly four decades in the Hamptons hospitality industry and owns celebrity clubhouse Nick & Toni’s along with Rowdy Hall, La Fondita and Townline BBQ.
“By the end of summer, everyone’s exhausted, and staff looks forward to a slower pace.”
Except these days, servers and line cooks may have to keep the proverbial Red Bull handy a little longer — which might not be a bad thing in today’s wobbly economy.
“I do not particularly celebrate the crowds leaving, but it does vary year after year,” East Hampton local Vanessa Gordon told The Post. “Many now stay through Columbus Day weekend or even the holiday season.”
Smith says fall is great for visitors, with less crowded restaurants and seasonal activities replacing busy beach days.
“It stays pretty strong on weekends until Thanksgiving,” Smith explained.
Beach clubs to ‘cozy’ content
Increasingly, “Hamptons Fall” has developed its own identity.
Missoni bikinis give way to Ralph Lauren cable knits and Uggs as influencers descend on pumpkin patches, corn mazes, and farm stands for another round of carefully staged content.
The longer season may annoy some yearlong residents yearning for their quiet streets back, but it has brought obvious benefits to businesses that once relied on a few jam-packed summer months to carry them through the year.
It has also paved the way for a different kind of tourism: visitors drawn for the “aesthetics” and the “vibes.”
Search interest for “Hamptons fall” has doubled in the last year, according to Google Trends, while online itineraries showcasing autumn weekends around apple picking, foliage, pumpkin patches and “cozy” fashion are candy — or at least candy apples — for social media swipers.
Other off-season draws, like the highbrow Hamptons International Film Festival in October, give visitors another reason to return after the beach clubs have packed up.
For locals and service workers in seasonal towns, a subtle tension brews like a pot of hot cider. Should they welcome those who treat their town like a mere content backdrop, even if they help real communities once fall hits?
Tourism rebrand
Small business associations and tourist advocacy groups in places like Westhampton and Montauk are saying “absolutely.”
In 2023, Discover Long Island, the region’s official destination marketing organization, campaigned to rebrand Tumbleweed Tuesday as “Tourism Tuesday” in an effort to encourage off-season travel to East End.
“We’re now active year-round, with visitors contributing to the local economy beyond summer,” a representative for the organization said, citing $8.4 billion in annual visitor spending.
The organization argues that in this uncertain economy, encouraging visitors post-Labor Day is essential to local peace of mind.
“We work hand-in-hand with our industry partners in Suffolk County to keep this year-round momentum a priority,” said the rep, adding that the goal is to help businesses “thrive 365 days a year.”
The fading post-Labor Day divide isn’t limited to the Hamptons.
On the Jersey Shore, many hospitality workers find themselves exhausted but flush with cash at the end of a busy summer season and celebrate the less chaotic months ahead, Tommy Jannarone, owner of Bar Antipication, told The Post.
Jannarone said locals enjoy empty beaches and restaurants, but the long winter makes summer special.
“Without the off-season, the summer season on the Jersey Shore wouldn’t be as electric,” Jannarone said.
But he, too, has watched the once-abrupt ending taper gradually.
“Since Covid, many more people live in their summer houses year-round as they can work remotely,” he said, adding that more visitors now take advantage of the “shoulder months” leading to and from the high summer season.
That popularity isn’t always welcomed by locals.
In the weeks leading up to Tumbleweed Tuesday, social media star and Dairy Boy brand creator Paige Lorenze was taken aback when a Nantucket shop installed an engraved wooden sign at the front declaring “No influencers.”
But Rebecca Chappa, owner of the popular Flying Minnow airport boutique, has gone the opposite route as summer comes to a close and, with it, the floods of high-rolling tourists.
“Nantucket doesn’t just suddenly get cheaper in the winter when the visitors leave,” she wrote on Instagram.
That’s why instead of giving content creators the boot, she’s choosing to cautiously welcome the influx of TikTok starlets and Twitch hype boys who visit the island in search of views, vibes and a chance to emulate the style of preppy Pinterest main characters like JFK Jr. and Carolyn Bessette Kennedy.
At her popular shop, the Flying Minnow, Chappa recently hung a handpainted shopping bag that read “INFLUENCERS AND DAIRY BOY OKAY… BUT YOU GOTTA ACT RIGHT.”
