Built for Suburbia: Retail Development on the Post Road (1960–1980)
The Connecticut Post Mall broke ground in 1960, backed by New York developer Sol Atlas.
It opened as an open-air retail complex in Milford, Connecticut, on a stretch of Route 1 known as Boston Post Road, which is lined with car dealerships, diners, and hardware stores.
Atlas saw an opportunity in the rising suburbs, where families needed easier access to shopping without heading into New Haven.
Two anchors bookended the new mall: W. & J. Sloane, a high-end furniture chain, and a Stop & Shop supermarket.
These weren’t boutiques—they were big names in postwar retail, and they signaled that the mall wasn’t an experiment. It was built to sell.
Then, in 1962, Alexander’s opened its sixth store there. The department store had a reputation in New York, and its move into Connecticut gave the mall new clout.
Early newspaper ads promised deals on outerwear and home goods. Outside, there were no walls—just sidewalks, benches, and storefronts facing the parking lot.
That setup didn’t last. A fire hit the west end sometime in the early years. Instead of rebuilding the same way, Caldor moved in—offering discount goods under fluorescent lights. The mall adjusted quickly.
Shoppers came from West Haven, Orange, and Bridgeport. By the late ’70s, traffic often backed up at the mall’s entrance on Saturdays.
Clerks ran registers at RadioShack, Thom McAn, and Woolworth’s. Kids bought vinyl at Musicland.
It wasn’t air-conditioned, and it didn’t need to be. But by the end of the decade, other malls in Connecticut had started enclosing their spaces, offering weatherproof browsing.
Connecticut Post Mall would follow soon. Back then, this mall was one of the most visible things to do in Milford, Connecticut.
Families stopped in after Little League games, teens passed hours between school and dinner, and shoppers stayed until the lights blinked at closing.
Mall Wars and Makeovers: Tenant Turnover and Legal Battles (1981–2000)
By 1981, the Connecticut Post Mall had a roof. The entire complex was enclosed that year, trading its open-air walkways for carpeted corridors and centralized air conditioning.
It was a practical move. Winters had gotten colder—or maybe shoppers were less tolerant. Either way, enclosed malls were becoming standard across the region.
A decade later, the mall saw more construction. In 1990, it added a new food court called the Skyview Café. It faced inward toward the heart of the building and pulled in more weekday lunch traffic.
Around the same time, Alexander’s closed. JCPenney took over that spot in August 1991.
G. Fox opened in 1991, only to be rebranded as Filene’s two years later. Department store names shifted often during that period—Filene’s absorbed G. Fox, and Macy’s absorbed Filene’s.
For shoppers, it meant familiar escalators but new signage.
Caldor closed in May 1999. The building sat empty for a while before demolition crews came in. Stop & Shop also moved out around then.
The grocery store relocated to a freestanding property nearby. Its old space was cleared to make room for Sears.
Behind the scenes, the mall’s owners were busy with attorneys. From the mid-1990s through the early 2000s, Connecticut Post Mall filed over 15 lawsuits trying to block the New Haven Galleria at Long Wharf.
That proposed project threatened to bring a rival mega-mall just ten miles away. It never got built.
Bigger, Brighter, Busier: Mixed-Use Expansion and Anchor Shuffling (2001–2010)
Starting in the early 2000s, Connecticut Post Mall expanded again—this time on a larger scale.
The old Caldor site was demolished, and construction crews moved in to add new wings, more parking, and two major anchors. The project cost $118 million.
Between 2005 and 2006, the mall added 480,000 square feet. A third level was built above Filene’s, which would later become Macy’s in 2006.
Dick’s Sporting Goods and Target opened during this same period, joining the property as full-scale anchors.
Both stores were placed on the south end, where Caldor had once stood.
The expansion wasn’t only about big-box stores. A 55,000-square-foot theater complex opened, replacing the nearby Milford Fourplex.
Originally launched as Cinema de Lux, the theater changed hands more than once—first becoming Rave Cinemas, now operating as Cinemark.
It drew weekend traffic even when department store sales lagged.
A new food court replaced the Skyview Café. It was brighter, with more seating, and closer to the movie entrance.
Chain restaurants and quick-service counters filled in fast—Sbarro, Panda Express, Auntie Anne’s.
Teenagers lingered after matinees, and families stopped in before errands.
Parking was always a problem, so the expansion also included a multi-level garage.
Drivers could finally park without circling for 20 minutes. That helped during the holidays when Target’s shelves emptied out faster than they could restock.
In December 2015, Westfield sold the property as part of a five-mall transaction valued at $1.1 billion.
Ownership shifted to Centennial, a real estate investment group based in Dallas.
At the time, the mall was the largest in Connecticut—three floors, five anchors, a cinema, and hundreds of retailers spread across more than a million square feet.
New Owners, New Challenges: Tenant Departures and Experience-Based Leasing (2011–2020)
After the 2005–06 expansion and the 2015 sale, Connecticut Post Mall shifted strategies.
Westfield was out. Centennial Real Estate, a Texas-based mall operator, took over during a period when national chains were pulling back from physical stores.
JCPenney, which had held a spot since 1991, closed in 2017. That space didn’t stay dark long—Boscov’s replaced it as part of a broader effort to modernize the mall’s lineup.
Sears, one of the last original-style anchors, lasted until late 2018. Its closure wasn’t a surprise.
The company had already pulled out of other malls across the Northeast. By then, the Milford location had been stripped of many of its departments.
The space sat empty while Centennial pitched a redevelopment plan.
To keep traffic up, management leaned into entertainment. Dave & Buster’s opened in November 2018.
Located near the center of the mall, it filled some of the space left behind by declining specialty retailers.
Muse Paintbar followed in May 2019, offering walk-in art classes with drinks. Later that summer, Guacamole’s, a sit-down Mexican restaurant, opened.
By 2020, Centennial pitched a new project for the empty Sears space: a mixed-use development called The Post.
The plan included apartments, open green spaces, and restaurants. But zoning questions stalled it.
Milford’s Planning and Zoning Commission declined the first version. In the meantime, Cast Iron Restaurant was announced in 2021.
That deal moved forward, even as larger redevelopment remained on hold. The retail base was thinning, but the mall stayed active by filling gaps with experience-first tenants and food concepts.
What Comes Next: Demolition Approvals and Residential Conversion (2021–2025)
P.F. Chang’s began construction in 2023, taking over the former Bar Louie space near Macy’s.
Nearby, new food concepts opened quickly—Sunrise Café, Pho Fusion Hub, and CasaCuba.
These restaurants focused on fast-casual meals with indoor seating. Some offered outdoor tables facing the parking lot.
Centennial hadn’t given up on the idea of adding housing to the Connecticut Post Mall site.
Discussions continued behind the scenes, even after initial pushback from local officials.
The old Sears building was still there—closed, quiet, and boarded up in parts.
In October 2023, The Milford Planning and Zoning Board approved a new proposal. It allowed the Sears site to be razed and replaced with up to 750 residential units.
The project would be implemented in three phases: Phase 1 by 2026, Phase 2 by 2028, and a final phase completed by 2033.
Local residents have mixed feelings. Some worry about traffic or school crowding, while others welcome the apartments.
What’s clear is that the mall is shifting from retail to mixed-use. Whether that shift sticks will depend on how fast Centennial moves and how the market responds.
Milford’s biggest mall keeps shifting—anchor stores out, new flavors in, apartments on the horizon.