Stroll down Main Street any weekend night and it’s hard to take downtown leaders’ fears seriously that it’s in any danger of dying. Crowds of young people spill out of the Regal Hollywood 20 cineplex, traffic is thick with cars searching for that rare streetside parking spot, and good luck trying to find somewhere to eat without a reservation.

You’ll see few people shopping, however, and for good reason. Out of the 40 shops (not including restaurants) on Main Street, only about seven stay open past 5 p.m., when most people shop. And too many of those stores, both inside and out, look dated and dingy, with smudged, dark windows and a strange mixture of merchandise. The Bullet Hole is a prime example: The combination gun shop-travel agency has a huge stuffed wild boar standing near the door and dozens of other dusty wild animals hanging on the wall above a poster for Sandals resorts. Funky charm of our old Sarasota? Absolutely. But it’s probably not a store many visitors or residents think of when they want to shop.  

The strains on Main Street—the older folks versus the younger, the newer residents versus those who have been here a long time and like things just the way they are—have Greater Main Street Merchants Association president Ernie Ritz sounding the alarms.

Ritz likes to tell a story about a downtown candy merchant who closed at 5 p.m. on Halloween. “I was having a Halloween party and ran out of candy,” he says. “So I run across the street, knock on the door and [the merchant] points at her watch,” indicating she was closed. “It was one minute past and she wouldn’t open up. I couldn’t believe it.”

Ritz is especially concerned now that a half-mile away, the glitzy, mammoth Sarasota Bayside project at the former Quay site—which is promising 140,000 square feet of high-end retail, restaurants and hotels—received its final approval. A few weeks earlier and five miles east, Benderson’s upscale $183-million University Town Center, with an estimated $500 million in annual retail sales, got the green light.  

Ritz and other downtown advocates are hoping Pineapple Square, which promises 812 public parking spaces, 276 condos and 30 to 40 new retail stores, will make Main Street the downtown destination. But, with the real estate slowdown and still more city approval hurdles to clear, it’s not certain when Pineapple Square’s downtown retailers—if they come—will be able to open. So far, only Brooks Brothers, Pastry Art and Sur La Table have confirmed they’re coming.

“The competition for shopping is surrounding downtown,” Ritz says bluntly. “If downtown doesn’t do something, it’ll be dead. The first one out of the ground wins.”

Adding weight to Ritz’s assessment is world renowned planner and New Urban Congress cofounder Andres Duany, who returned to town last winter to evaluate how the city has realized the master plan he designed seven years ago.

“Your Main Street may take a really big hit when Bayside happens,” Duany told a crowd at City Hall and later at a Downtown Partnership dinner. “You have to get serious very quickly.”

Ritz has been working with his Merchants Association to develop a retail strategy, and the group is spending $10,000 to bring national retail expert Bob Gibbs to Sarasota May 5 and 6 to lead a charette. Gibbs, who is familiar with Sarasota as a former consultant for Pineapple Square developers Bill and Butch Isaac, will tour downtown much like Duany did, and give his opinions on what it needs to do to be competitive.

"Gibbs takes a critical eye of things we get used to seeing," says Ritz, who, as a local rep for Pineapple Square, has a major stake in making sure Main Street cleans up its act. "We'll come up with a plan for storefronts, streetscapes and a retail strategy."  

Most likely, Gibbs also will be eyeballing one of Duany’s pet peeves: our lack of easy access to the downtown bayfront by dangerous and busy four-lane U.S. 41. Providing a safe way for pedestrians to cross from Main Street to Bayfront Park—with its green lawns, gorgeous views and two popular restaurants—was a major component of Duany’s downtown master plan in 2000. He’s livid that a small group of influential citizens (he called them “a tyrannical minority” of “old coots”) convinced the city commissioner to quash the plan.

Still, not everybody is buying the doom-and-gloom scenario. After all, downtown now has Whole Foods, a Starbucks, several new restaurants and retail stores and hundreds of condos, however unoccupied they may be. Planned hotel projects promise hundreds of downtown rooms.

Many downtowners say the area has always been quirky, with the unpredictable operating hours and a hodgepodge of stores—The Bullet Hole included—all part of its charm.

“People who are interested in books are going to come to us,” says Dan Christian, manager of Parker’s Books, a beloved used bookstore that’s been on Main Street for 27 years. Parker’s, which claims to have one of the Southeast’s largest collections of rare, out-of-print and antiquarian books, has been through renaissance and decline and about five downtown revitalization plans.

So, too, has John Harshman, who manages downtown property from his Harshman & Co. commercial real estate office on Main Street.  “I disagree with Duany’s statement that Bayside is going to kill downtown,” says Harshman. “It’s going to be an asset that will only help to enliven the area.”

He points to Plaza at Five Points and a handful of new condo developments as one of the prime differences between Main Street now and its cycles of highs and lows that saw developments such as the indoor Main Street Plaza mall and the Quay come and go.

“The health of downtown is measured by residents and office. Following that will be the retail,” Harshman says. “We don’t have to have Nordstrom. We have some good retailers and we’ll get others.”

Argus Foundation executive director Kerry Kirschner, who has lived in Sarasota since the 1950s and was mayor and a city commissioner during the 1980s boom and bust, says today’s debate is much the same even if the city looks different. As always, the biggest problem with trying to “save” downtown from the new development bogeyman, he says, is the lack of consensus that there’s a problem.

Even among those who do feel downtown retail is lacking, there’s little agreement on the best solutions. Duany sees connectivity to Bayfront Park and slowing down traffic on U.S. 41 as key to keeping downtown vibrant. Tony Souza, director of the 350-member Downtown Partnership of Sarasota, agrees but also sees the establishment of a historic district—restoring the facades of 1920s buildings, adding brick paved streets, period lighting, and signage—as a niche that will separate downtown from the newer retail districts. Souza has been promoting a historic district since he arrived in town two years ago from New Bedford, Mass., where he created a similar district. He’s been working with the Sarasota County History Center to identify architectural styles distinctly Sarasota. “If you don’t preserve your past, it becomes generica,” he says. 

For some merchants, however, downtown survival is just a matter of getting stores to stay open later. Most close at 5 p.m. and only a few open on Sundays.

Take Freaky Tiki Surf Shop owner Monica Eshkoli, for example. She and her husband opened their Main Street surf and clothing shop three years ago for the 30-and-under crowd. They stay open seven days a week, well into the evening. “One of the biggest challenges is that none of the other stores want to stay open past six,” says Eshkoli. “It’s a ghost town on Sunday. If you look at St. Armands, it seems more of a shopping destination.”

Sharon Abell, manager of Encore & More, a consignment store on Main that’s been around for 13 years, says late hours aren’t possible. “We are totally volunteer-driven,” she says. “We don’t have the manpower to handle being open later.”

With more than three dozen individual landlords, it’s impossible to enforce uniformity in storefronts and business hours the way a mall can, and a historic district won’t fix that. Mark Kauffman, a downtown landlord and developer for 30 years, doesn’t buy into the idea that Main Street is in danger, but he supports the historic district.

“It’s a unique idea,” Kauffman says. “You need to do something to keep up with other projects such as Bayside. But there’s always going to be a place for Main Street.”

Everyone agrees downtown has been transformed, for good or for bad, depending on you point of view. "We are going to meet the challenge,” so downtown doesn’t die, Ritz says.

Even Duany, who pulled no punches during his recent visit, gave the city credit for what it has accomplished.  

“It’s barely recognizable,” Duany said. “The pace is extraordinary. The place looks so much better, and it’s working better for those living downtown.”