07 March 2023

Chesapeake Square, Chesapeake, VA

 A dead mall

1- Chesapeake Square grand opening ad from the Daily Press in 1989.  View the full PDF version here.  2- The new entrance off of Taylor Road. (Source)

Chesapeake Square will always occupy a special place for me as the earliest mall whose grand opening I attended, so it was 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.  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 slated to open the following spring.

Chesapeake Square mallmanac ca 1989.  View the full PDF version here.
Chesapeake Square mallmanac ca 2000.  View the full PDF version here.

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.  The main entrance was home to a Morrison’s Cafeteria on one side and a Ruby Tuesday on the other.  The mall had everything and seemed like it was headed for great success.

1- The main entrance. (Source)  2- The food court. (Source)  3- The old Sears entrance. (Source)  4- The new look entrance at the mall's east end. (Source)

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.

1- Chesapeake Square's early 2000s layout.
2- Chesapeake Square lease plan ca 2011.  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 a new building) remain as the only large tenants, and the only entities keeping Chesapeake Square alive.  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 1898 will still be there should I ever return.

Chesapeake Square pamphlet ca 2021.  View the full PDF version here.

Chesapeake Square official website

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