My first trip to pioneer square since before the pandemic and I cannot find a parking spot. It’s only 11 a.m. on a Thursday. Clearly, not everyone with an office here is working from home.

I’m meeting with Lisa Howard, executive director of the Alliance for Pioneer Square, a nonprofit organization dedicated to preserving “what makes Pioneer Square the most authentic, engaging and dynamic neighborhood in Seattle.” As you can imagine, Howard is bullish on the future of one of the city’s oldest and most historic neighborhoods. I’m going in with an open mind, though I’m fighting my skepticism.

I remember Pioneer Square for its party atmosphere decades ago and, more recently, its First Thursday Art Walks, funky retail shops and abundance of cutting-edge art galleries. But I also know it as the place where acquaintances on three separate occasions were punched while either leaving work or simply walking around; for the time someone asked me if I was “scared of a man with a gun;” and the place where a colleague told me she literally sprinted back to the office to elude a man chasing her in broad daylight.

Like all neighborhoods, Pioneer Square has its share of challenges. Crime is among them, but perceptions often trump reality. Property crime is actually lower in Pioneer Square than in Fremont or Wallingford, according to Seattle Police Department statistics. “Violent” crime is a bit higher, but not significantly. Clients of the numerous social service agencies in the neighborhood spill into the streets, often creating misleading impressions.

Pioneer Square, often referred to as Seattle’s “original” neighborhood, has roots dating back to 1853. It was rebuilt with distinct, Romanesque-style buildings after the Great Seattle Fire of 1889 burned down the neighborhood. In 1970, the Seattle City Council named 20 square blocks in Pioneer Square an historic district. It later became the city’s first neighborhood to be listed in the National Register of Historic Places. “It’s a small town in the middle of a big city,” says Jane Richlovsky, an artist and co-owner of the Good Arts Building, home to 30 artist studios.

Katherine Anderson, co-owner of popular restaurant and retail shop London Plane, says Pioneer Square could have resembled Greenwich Village back when it was known as New York City’s counterculture neighborhood. “It’s a shame,” she says. “It has just been beset by problems for decades.”

Today, the $740 million waterfront improvement project and removal of the elevated Alaskan Way Viaduct creates unprecedented opportunities. Roughly two dozen development projects, with both public and private investment, are either underway or planned. Many were hatched in anticipation of the viaduct coming down. Most neighborhood advocates are supportive, though some remain wary that development could threaten the neighborhood’s gritty, quirky reputation as “the Brooklyn of the Pacific Northwest,” as Aaron Barthel, co-owner of Intrigue Chocolate Co., puts it.

As head of the neighborhood association, it’s a concern Howard hears often. She wonders herself, but she’s confident that developers will “mindfully integrate” their projects into the current infrastructure and maintain what she calls “authenticity.”

This is far from the first time that Pioneer Square has occupied the spotlight as “the next big thing.” Property developers envisioned it as ripe for urban renewal in the 1960s until the historic designation restricted development. More recently, it’s become a darling of the tech startup community. It gained further acclaim when timber giant Weyerhaeuser moved its corporate headquarters to the neighborhood in 2016.

Pioneer Square still serves as the city’s arts district, with about four dozen galleries large and small and countless funky, locally owned boutiques among its roughly 575 businesses. “It’s the opposite of  University Village, and I’m perfectly happy going to U Village, but there are no chain stores here,” Anderson says. “It’s all beautiful, unique, special places. It’s just a beautiful, European-style neighborhood.”

One significant element it lacks is housing. The neighborhood contains only about 2,500 households and fewer than 4,500 residents, according to the 2019 Community Survey. That’s slowly changing, but the Pioneer Square housing market is constrained by both geography and development restrictions that limit the height of buildings to 120 feet.

They won’t add significant housing stock, but several multifamily projects are underway or well into the planning stage. These include a three-story adaptive-reuse project being developed by Urban Vil-lages at 115 S. Jackson St. with 26 fully furnished apartments as well as a taqueria, wine bodega, beer garden and bike club on the ground floor; and the Canton Lofts, a Nitze-Stagen Opportunity Zone LEED project with 80 loft-style apartments. King County has purchased the development as part of its Health Through Housing Initiative that seeks to provide affordable housing.

The nonprofit Chief Seattle Club is preparing to open an eight-story, mixed-use project that includes 60 units for people experiencing homelessness and another 20 affordable units. It will also feature spaces for Chief Seattle Club programs, a gallery/café and a primary care clinic. Urban Visions plans a 5,000-square-foot, 120-foot-tall residential tower at 165 S. Washington St.

The housing conundrum is a personal one for Tija Petrovich, Barthel and his partner, Karl Mueller, and Richlovsky. All live and work in the neighborhood and insist that increasing the housing supply is crucial for its evolution. Richlovsky in particular has a unique perspective as a building owner, landlord, working artist and 10-year resident.

“When I’m walking around, there’s a sense of community. The creative entrepreneurs, the independent restaurant owners, the small retailers, the artists and art gallery owners all recognize each other’s value. We have this symbiotic relationship. Seriously, everybody knows everybody else. I like to call it ‘Mayberry RFD,” she says. “But more housing down here would make it better.”

Petrovich has lived in the neighborhood for three decades, served on the board of the Pioneer Square Residents Council for more than 10 years and is currently its chairwoman. She owned Seattle Fitness in the neighborhood for 25 years before the pandemic emptied office buildings and erased the corporate clientele her business had depended on for years. She reluctantly closed Seattle Fitness in the summer of 2020, writing a heartfelt letter thanking members for their longtime support.

“People either get it and understand Pioneer Square or they don’t,” says Petrovich, who notes that the neighborhood gets a bad rap for its perceived lack of safety. “This is such a vital area, but every chance I get, I talk about housing. The community isn’t going to exist with a bunch of buildings and businesses. Those are the arms and legs, but the residents bring heart. I’d love it if we had 10,000 residents here, but that’s years and years away.”

Howard says Pioneer Square has fewer obstructionists than in years past and, as a whole, has become more pragmatic about development that preserves its architectural and cultural history. She notes that there’s an abundance of “investment and intentionality” surrounding the waterfront redevelopment and its potential to connect Pioneer Square to downtown and Pike Place Market. “It’s just going to draw so many more people into downtown and the waterfront and it will be an asset for Seattle as a whole,” she predicts.

She acknowledges, however, that the neighborhood will miss many of its institutional businesses that have left in recent years, including those like Seattle Fitness that fell victim to the pandemic.

Seattle E-Bike, for instance, moved its shop from Pioneer Square to West Seattle in the summer of 2020, citing violence and an unsafe atmosphere. Pay-equity startup Syndio Solutions earlier this year said it wouldn’t renew its sublease in the neighborhood for many of the same reasons. The popular Fuel Sports Grill decamped for Ballard’s Crown Hill neighborhood after 15 years in Pioneer Square. Several other well-known bars and restaurants are also gone, including Manu’s Bodega, Copal, Pacifica, Biscuit Bitch, Bisato and II Corvo. Howard adds that change is inevitable in any neighborhood, citing the closure of Planet Java because the owners retired and the loss of Epic Brewing prior to the pandemic.

Taking their places are a number of new businesses and developments. Bisato has already been replaced by a restaurant called 84 Yesler. One developer, Urban Villages, is so upbeat about the neighborhood’s potential that it is pursuing four separate projects it calls Railspur Seattle, named for the railways that once traversed the area.

Besides the mixed-use apartment project at 115 S. Jackson St., Urban Villages is developing a 120-room boutique hotel at 100 S. King St. slated to open in the summer of 2023 and is renovating the former FX McRory’s restaurant at 419 Occidental into a modern office building with a retail component. All broke ground last year, and the company says the projects are the largest, LEED-Platinum, historic preservation efforts in the country. It is also “activating” two intersecting alleys in the neighborhood with live music and pop-up events and is currently marketing retail spaces on the alleys between 250 and 5,000 square feet.

Other developers are constructing new hotels and office spaces. One, Unico Properties, is rehabilitating three buildings built between 1889 and 1909 on the “Grand Central Block,” between Washington and Main Streets. The project is in predesign and prereview.

“The historic charm of Pioneer Square is unlike anything I’ve ever seen,” says Jon Buerge, chief development officer at Denver-based Urban Villages, which began buying the parcels back in 2010. “Pioneer Square didn’t get hit with urban renewal like a lot of other neighborhoods did. What really stood out to me was how much of the historic fabric was intact. It created a special atmosphere that was kind of unusual.”

Buerge says alley activations are popular overseas and points to the intimacy and charm of Post Alley at Pike Place Market as an example of a successful street. All three Urban Villages projects will have direct access to the intersecting alleys. The company is also seeking a code amendment to build a rooftop restaurant on top of the hotel.

Visitors to the neighborhood will notice other changes. As part of the waterfront development program, the city will create a number of “East-West” pedestrian improvements, including widening sidewalks, increasing greenery and reducing the number of vehicle lanes on portions of King, Main and Washington Streets, Yesler Way and Second Avenue South. The future arrival of the much-anticipated Sound Transit III expansion will connect Pioneer Square via light rail with several new neighborhoods, including Ballard and West Seattle. A rebuilt Alaskan Way from South King to Pike streets will include dedicated lanes for transit in and out of downtown and lanes to access newly renovated Colman Dock.

“Why wouldn’t you want to be in Pioneer Square?” asks Jane Hedreen, owner of Flora + Henri boutique, a luxury children’s and women’s apparel store. “Is this the hub of every transit in Seattle? There’s just so much that’s going to be happening in the next five years here. I would think for someone on the Eastside, this would be like a trip to Brooklyn.”

For Howard, the future is less about “fixing” the neigh-borhood and more about improving it. She has a handle on virtually everything happening, ticking off a dizzying array of developments and activities during a recent walking tour. In her mind, the distinct parts of the neighborhood all work together: Artists, boutique retailers, tourists, overflow stadium crowds, upper-floor office workers, and restaurants and bars combine to create a compelling and unique Seattle experience.

“If it was just one thing, I don’t think Pioneer Square would be so important to so many people. And I think people are very passionate about Pioneer Square,” she says. “There’s the intersection of all aspects of life in this one spot and you’re able to experience it, whether it’s drinking a latte in the sunshine right before your workday starts, being part of an art walk or walking around in the dark with the lights over the holidays. “I think people are going to be surprised when they come back down.”

Regardless of that evolving landscape, Pioneer Square will never become something it’s not, says Judith Rinehart, who opened her business, J. Rinehart Gallery, in the neighborhood in 2019 after researching spaces downtown, in Belltown and South Lake Union. Its very identity is wrapped in its mash of virtually everything, good and bad, in just 20 square blocks.

And that’s OK.

“It’s not glossy and it’s not shiny,” she says. “We kind of accept everyone that’s here and you have to be good with that.”

There’s big money riding on it.