Chesapeake Square, Chesapeake, VA

 A dead mall

-UPDATE BELOW-

22 November 2025

(Source)

Chesapeake Square will always occupy a special place with me as the earliest mall whose grand opening I attended, making it the first place I knew from the very beginning.  In the autumn of 1989 we took the long ride from our home in Virginia Beach to the western fringes of the Southside to see the new, sprawling one level facility.

Chesapeake Square Mallmanac ca. 1989.  View the full PDF version here.

There was much fanfare as large crowds had gathered to see the opening of Sears, Hess’s and the mall shops in between.  Occupying lots on the front side of the structure were the two other original anchors, JCPenney and Leggett, which were still under construction and slated to open the following spring.

-UPDATE-  1- The former Sears store.  2- JCPenney before closing.  3- Burlington’s home in 2018 was originally Leggett.  4- The exterior doors to what was Hecht’s before Macy’s.  5- The mall entrance to Sears at Chesapeake Square’s far western end.  6- The closed opening to Hecht’s.  (Source for all)

The interior corridor was adorned in pastel tiles, a calling card for its age, and shops of the day like Spencer, K&K Toys, Waldenbooks and Lechter’s.  The large, centrally located food court hosted spaces for Corn Dog on a Stick, Hot Dogs and More, Original Cookie Company and Sbarro’s.

Chesapeake Square lease plan ca. 1999.  View the full PDF version here.

Chesapeake Square’s main entrance was home to a Morrison’s Cafeteria on the west side and Ruby Tuesday to the east of the doors.  Its nautical themed logo occupied a prominent space under the steeple like main entrance adornment.  The mall had everything and seemed like it was headed for great success.

Chesapeake Square Mallmanac ca. 2002.  View the full PDF version here.

Chesapeake Square later added anchors Montgomery Ward (which moved from nearby Tower Mall, which Chesapeake Square all but supplanted as the area’s main retail center) and Hecht’s.  Dillard’s, which had taken over the original Leggett’s and Hess’s spaces, closed in 2009 with one location opening later as a Burlington.  The mall seemed to be headed for the same demise as the mall it had killed, though in shorter time.

Chesapeake Square lease plan ca. 2010.  View the full PDF version here.

The rest of the traditional anchors had already closed shop before JCPenney, the last of the original four, closed in 2022.  Burlington and Target (opening in the old Montgomery Ward space but in an expanded building) remain as the only large tenants, and the only entities keeping Chesapeake Square alive.

-UPDATE-  Chesapeake Square pamphlet ca. 2015.  View the full PDF version here.

There has been redevelopment talk, but besides a demolition of the old Macy’s, JCPenney and Sears, nothing concrete has been released.  I hope that some of the future plans involve keeping a significant portion of the original building so at least a little bit of what I first saw on that crisp autumn day in 1989 will still be there should I ever return.

Chesapeake Square pamphlet ca. 2020.  View the full PDF version here.

-UPDATE-

-22 November 2025

It was over two decades since my last visit, but I finally made the return to Hampton Rhoads in the autumn of 2025.  After a scenic ride on the number 45 bus, complete with an accident blocking a railway crossing and all, I found my way to the remnants of Chesapeake Square on Portsmouth Boulevard.

1 to 4- The front parking lot of Chesapeake Square with the remains of Sears to the left of the main entrance and what’s left of Leggett to the right.  5 to 8- The main entrance hasn’t changed much since the center’s 1989 opening.

Over the past several years I hadn’t been keeping a really close watch on recent developments for the shopping center, so I was disappointed when I saw that another portion of the complex had been laid to rubble.  What originally opened as Leggett a few months after the debut of the main facility has been unceremoniously rendered obsolete.

That left the northeast anchor on Chesapeake Square’s flanking side as the final remaining anchor building.  Once host to Montgomery Ward, Target still finds a home within its confines.  Fortunately, the store still seemed to be doing well and has been integrated into all future redevelopment concepts.

1- Chesapeake Square’s eastern front entrance.  2 to 5- A new eastern entrance and the Cinemark Theaters occupy the spot once home to Hess’s.  6 & 7- Target, originally Montgomery Ward.  8 to 10- The mall’s rear entrance leading to the food court.

I arrived at the same nautical themed main entrance that I remember from 1989 to see that, although it was right at the center’s opening time, the doors were still locked.  I spoke with one of the members of a tight knit group of mall walkers waiting with me.  He shared the same concerns as I about the state of indoor shopping malls and how much more difficult it would be for them to find an equivalent meeting space once they’re all gone.

Chesapeake Square Mallmanac ca. 2023.  View the full PDF version here.

Right at ten when the locks were finally released, I joined the rush into Chesapeake Square.  I was pleasantly surprised to see that, minus its entire western third, the place was every bit as late eighties fabulous as it was all those years ago.  The pastels were faded and the tired planters hosted less greenery than the deserts of Mars, but it was every bit the mall I saw on its opening day.

1- Just inside the main entrance.  2- Behind this temporary wall was the western third of the main concourse.  3 to 10- Chesapeake Square’s center court.

To the west of center court a lone strip of caution tape separated us from the temporary wall built where the western third once stood.  Just in front of me, the food court was almost completely vacant save for one or two local outfits.  But the holiday decorations were still being added to the corridors in what seemed to be a vain attempt for some kind of normalcy.

Chesapeake Square pamphlet ca. 2025.  View the full PDF version here.

It wasn’t long before I made my way to the eastern end of the truncated concourse where I met the proprietor of Master Hill’s Red Dragon Martial Arts.  We bantered for a few minutes about growing up in malls such as these and how disheartening it is to see them all go.  He viewed his students and even the mall walkers sure to show up every morning as good friends and lamented that the end date seems to be approaching as the bulldozers do their work.

1 to 4- The expansive and early empty food court just beyond center court.  5 & 6- The eastern concourse.  7 to 10- The court between the original Leggett and Montgomery Ward anchor stores.

Crisp air and blue skies greeted me as I exited Chesapeake Square, perhaps for the last time, at its eastern end.  Once the egress to Hess’s but now leading to a strip of asphalt separating it from the Cinemark Theaters, I made my way to the flanking side toward the final remaining anchor- a Target outlet occupying Montgomery Ward’s former digs.

I was glad to see the archetypical darkened glass entrance ornamentation was still hovering over the store’s main entry, even though it was stained by years of neglect and exposure to the elements.  But just beyond I could see clear skies in the distance where, at one time, Hecht’s, Sears and the western portion of Chesapeake Square once lay.

1 to 3- The mall entrance once leading to Leggett.  4 & 5- Target née Leggett’s mall access.  7 to 9- The far end of the eastern concourse.  10- The former mall egress to Hess’s now leads outside.

Though I never had anywhere near the connection with Chesapeake Square as I had with Lynnhaven, Pembroke or even Greenbrier malls, it’s still sad to see what it has become.  On that autumn day merely 36 years earlier there was so much promise and excitement, most of which is now laying amongst the piles of rubble just beyond its walls.

Chesapeake Square official website