The Downtown Dilemma

Editorial Board on Apr 30, 2025

Last week, an Express Sessions event in Sag Harbor focused on the village’s shopping district and explored a puzzle: If last summer was the busiest ever, and the streets of Sag Harbor were, by all accounts, packed on most every day and evening, why were the owners of shops on Main Street and elsewhere in the business district reporting a down year?

The answers are elusive, complicated — and, in many ways, universal to every downtown shopping district on the South Fork, from Montauk to Eastport: Southampton, Bridgehampton, East Quogue, Westhampton Beach, Water Mill, Amagansett, East Hampton, Quogue, Hampton Bays. There are differences, but the similarities outweigh them, and the lessons are there for all to learn, and ideas to explore.

It was a distinguished panel, but one member stood out: Lisa Field is the owner of the Sag Harbor Variety Store. It is one of the iconic storefronts on the entire East End, a link to the past (actress Sue Lyon got her heart-shaped sunglasses featured on the legendary poster for the 1962 film “Lolita” from its shelves) and a living mecca of nostalgia. If the resurrected Sag Harbor Cinema isn’t the beating heart of the business district, certainly the Variety Store is.

Consider the role it has played just in the 55 years that Field’s family has owned it, and the changes it has seen outside its windows. It once served a factory town as a general store, but over the years it has evolved into a treasured time machine: Walk inside and you feel transported to another era.

But it’s not a museum — to stay alive, it must be tended, in the same way a garden must be watered and weeded. For a store, that means customers, and not just those poking around and sucking in the sentimentality. Simply put, they need to spend money.

It’s the basic equation that has become a problem for every brick-and-mortar retailer in any of these small towns: They must appeal to the summer crowd that swarms in with full wallets and spendthrift enthusiasm — but there’s also a desire to see them stay open in the offseason, which means appealing to year-round residents. It’s a tricky route to chart.

In the days of online shopping and big-box stores, it’s even harder for independent shops to stay in business. (And, as much as shoppers and locals alike love the big-name, high-end shops in our midst, they are not, ultimately, what year-round residents desire on main streets.) Just flipping a sign from “closed” to “open” isn’t enough these days — restaurants and retailers often need to provide an “experience” to keep the money flowing. That takes a sense of marketing, creativity and energy that not every businessperson possesses.

The challenges in Sag Harbor translate to most of the other downtown areas that neighbor it: parking, traffic, a lack of people who live in the downtowns, a dearth of late-evening opportunities even for summer strollers. That’s where chambers of commerce and local governments have to step in and provide a support system, stirring up excitement and giving folks a reason to visit. Sag Harbor’s active chamber recently held a “Keep It Local” weekend that was remarkably successful, showing that even simple reminders can get people to move from delighted window-shopping to actually supporting the businesses they love to see. One strong message that came out of the conversation is a simple directive: “If you love something, you have to support it. With money.”

But there are other answers. An important reminder came from the audience of The Express Sessions event, when former North Haven Mayor Jeff Sander suggested that the parking apps that have been deployed in Sag Harbor and other villages are woefully underused. Why not take advantage of the technology and move visitors to different spaces at different times of the day? That spot in front of a grocery store, perhaps, should be a 30-minute parking space at 11 a.m., but a two-hour spot after 7. Eating dinner at a local restaurant? Punch a button on your phone, and pay for a little more time — with the restaurant confirming that you’re actually there, spending money and using that space judiciously.

Sag Harbor isn’t a factory town anymore. For generations, Southampton and East Hampton towns were able to create an enclave where people either lived here or stayed here for longer stretches; Airbnb and other short-term rental options destroyed that customer base. The new summer visitor might only need a day or two of supplies, not three months. Ignoring those changes is pointless.

It’s not all doom and gloom. The discerning visitor remains affluent, and the region is still an enticing mix of perfect beaches, tempting restaurants and historic charm. Despite the economic and socioeconomic challenges, this is still a “gold coast” of sorts, and retailers and restaurants can find success. It’s like local shellfish: They’re a little harder to find these days, but a little extra effort and you’ve got a delicious banquet like no other place can serve up.