You may think of the Uptown District as a place to buy groceries, grab a bagel or drop off your dry cleaning, but to many city planners, it’s the poster child for how to do urban redevelopment right. Twenty years ago, there was nothing “uptown” about the place at all: It was an abandoned Sears store surrounded by an ugly, empty 14-acre parking lot.

In the fall of 1986 the city of San Diego bought the land for $9 million with the intent of building a new central library there. (Before you ask, yes that’s the same new library local politicians are still promising us today.) Instead the city council – at the urging of business groups like the 86-year-old Hillcrest Business Association – decided to develop the area as a high-density, mixed-use community catering to the pedestrian instead of the car. The result: A lively, livable neighborhood with 318 residential units – owner-occupied and rentals – and 145,000 square feet of office and retail space anchored by one of the most profitable Ralphs supermarkets in the entire chain. In 1991 the National Association of Home Builders selected the Uptown District as its Project of the Year.

Uptown’s intimate feel is the result of careful planning: For instance, all residential parking is underground, encouraging people to move around the complex on wide sidewalks arranged around a central park. The Ralphs parking lot is also underground freeing up the space in front of the store for outdoor cafes and other small businesses. The district’s retail shops face University Avenue and include wide openings that allow passersby to see into the heart of the complex. Then there’s that magnificent pedestrian walkway that spans Washington Street and effortlessly incorporates University Heights into the neighborhood.

The Uptown District has not, however, been an unqualified success. While the residences, Ralphs, and more recently, Trader Joe’s have been extremely successful, many of the restaurants, small retailers and travel agencies who set up shop there have failed. People may disagree as to why, but the economic reality is undeniable.

Nevertheless, the Uptown fan club extends well beyond the people who live and shop there. Urban planners from around the country make regular pilgrimages to the place and write about it in tones approaching reverence. Here’s how author Lee Sobel, writing in the urban planning journal The Town Paper, describes the brunch he and his wife enjoyed there one sunny Sunday morning in 2000: “While we ate, a group of hikers slowly assembled in front of Trader Joe’s for an all-day expedition. Locals converged on Deidrich’s Coffee for their morning cup and scone. People went in and out of the supermarket endlessly, only to return again, treating it like a neighborhood refrigerator…the Uptown District is a fun place.”

Not bad for a place that started out life as a deserted parking lot.