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When I told a friend I was going to check out Jamagansett over Memorial Day weekend, he thought it was a music festival. “Rock on!” he said — generously, given my straw basket bag and clogs. The reality was tamer: It’s a twee Hamptons shop that opened in the just-so village of Amagansett selling three $80 pies a weekend.

That price and quantity are set by Lena Kristy, who, after the San Francisco Cooking School and an M.B.A. program at Columbia, worked on consumer brands as a consultant at McKinsey. She left two years ago to start Jamagansett, a “luxury jam brand” that makes $25 nine-ounce jars of low-sugar preserves, often using Long Island fruit harvested during peak season. Kristy, who was raised in Marin County, California, bears a passing resemblance to Allison Williams, and if she were on Girls, she’d be Marnie: type A, wide-eyed, focused.

“Our vision is to become a household name,” says Kristy, who has a silent partner. On opening day, she buzzed around her cottagecore-coded store down the street from The Row as a stream of shoppers came in from the rain for jam samples and to try to grab one of the limited-edition salty blueberry pies. Two were already gone.

In a region where entertaining can be a blood sport, bringing a coveted dessert to your host is de rigueur, and each conveys its own subtle message: Briermere Farms’ cultish $45 strawberry cream pies are the insider’s pick (and mean you — or your house manager — trekked to Riverhead). Carissa’s $60 flourless chocolate cakes signal taste and a sensitivity to gluten-free guests. Round Swamp’s $44 apple pies are the rustic, earthy option.

“You go to someone’s house, you bring a pie,” says Lori Chemla, co-owner of Carissa’s. Chemla, who has opened three locations in East Hampton and Sag Harbor since teaming up with Carissa Waechter in 2017, recalls a time when it was customary for friends to bring homemade pies to casual beach potlucks or pick them up from farmstands. The shift toward more extravagant hostess gifts and away from the kitchen has been a boon for Carissa’s as well as Sagaponack General Store, reopened last year by Mindy Gray, the wife of Blackstone CEO Jonathan Gray. “What’s more American than apple pie?” she says, wearing a ticking-stripe apron. Hers sell for about $45.

In the land of short seasonal selling periods, high labor costs, and rising supply costs, this all-American tradition comes at a price. Chemla says baking requires expensive equipment and knowledgeable chefs. She and Waechter, who was trained at Daniel, also have a French baker and other career bakers on staff. And keeping a baked-goods business alive in the South Fork year-round inevitably means taking losses in the winter. “It’s a very particular seasonal specialized world that we live in,” Chemla says.

Kristy attributes the cost of her jams and pies, which are baked in a Southampton commissary kitchen, to the expense of doing business out East. And she acknowledges it was a strategic choice. “We’re covering our costs but also pricing them within the market to signal what type of brand we’re building,” she says. The sign outside the shop on Main Street might as well read WE ARE NOT SMUCKER’S. Her nine-inch, $80 pie actually used to cost $100. That was before Kristy heard quips such as “I’m going to have to get a second job to afford this pie” from persnickety customers who probably haven’t needed to work second shifts since junior high. She says she is still testing price and supply and may add more. So far, the pies have been sold on a first come, first served basis.

One of the customers who sprang for the salty blueberry pie was Licia Householder, who spent years as the pastry chef at Sagaponack’s Loaves & Fishes. Now a private chef known for custom cakes, she got sticker shock back when it was $100: “It’s a little ridiculous, to be honest.” While she found it delicious, a description friends of mine vouched for, she hasn’t bought another one.

Another rookie in the Hamptons baked-goods Thunderdome is Sag Harbor’s Gone Bananas Bread, the brainchild of Los Angeles stylist and interior designer Estee Stanley. A friend of Justin Timberlake’s who was with him on the night of his Sag Harbor martini bust, she has long had a summer home in Sagaponack. She first made banana bread in her kitchen during COVID’s early lockdowns to benefit the charity Baby2Baby and has gone on to open viral pop-ups at the Original Farmers Market and a store next to Brentwood Country Mart in L.A.

“It’s luxury banana bread — it’s Gucci,” says Stanley, whose loaves are priced from $40 to $60. “We’re in areas where people spend money. Like Brentwood, nobody really cares. Hopefully in Sag Harbor nobody really cares. Food ingredients, rent, employees — it all adds up. It’s not like we’re printing money and have hit the jackpot.”

Sam Pezzullo, a Sag Harbor filmmaker and the maître d’ at Tutto Il Giorno restaurant, is over what he calls “designer desserts.” He plops a $4 Hahn’s Old-Fashioned Cake Company crumb cake in front of me, singing its praises: “It’s just a good product.” He thinks cakes and pies are so popular on the East End in part because of the idealization of the ultimate rom-com occupation: running a bakery.

“Everybody out here wants to be Kristen Wiig in Bridesmaids,” says Pezzullo. Or the woman living out a real-life romantic comedy and business fantasy in East Hampton: Ina Garten. Her memoir, Be Ready When the Luck Happens, tells the story of her hapless bootstrapping rise. Her frozen-yogurt machine wreaks havoc; she sweats in the kitchen to churn out brownies. Kristy too talks about schlepping rhubarb from farms and testing jams in her kitchen. But her business background and investment cushion mean she can launch collaborations with influencer Seth Boylan and run Instagram marketing campaigns out of the gate.

For those uninterested in status desserts, there’s always the old-fashioned approach — bake it yourself. But personal chef Robyn Henderson-Diederiks offers a word of caution. The pies she makes for her clients using local farm-stand produce and good-quality flour and butter can cost up to $120 in ingredients alone, and that’s before her fee kicks in. Adding up her shopping list, she says, “It might be cheaper to buy the $80 pie.”