Chesapeake Square Mall in Chesapeake, VA – Storied Past, Present, and a Promising Future

A Look Back at Beginnings

Chesapeake Square Mall opened its doors in 1989, transforming the once forest and swamp land in the Western Branch section of Chesapeake, Virginia, into a bustling shopping center.

Developed by the Edward J. DeBartolo Corporation, the mall’s original anchor tenants included JCPenney, Sears, Hess’s, and Leggett.

Over time, the mall’s surrounding area expanded, giving rise to two other shopping centers: Chesapeake Center and The Crossroads at Chesapeake Square. Throughout its history, Chesapeake Square has seen various changes in its anchor tenants, which have shaped the mall’s evolution and identity.

The Early Years: Anchor Tenants and Retail Success

Year Event
1989 Mall opens with JCPenney, Sears, Hess’s, and Leggett as anchors
1992 Montgomery Ward opens

The opening of Montgomery Ward in 1992 added a new dimension to the mall’s retail offerings, attracting more shoppers to the area. As a result, Chesapeake Square quickly became a destination for residents in the Hampton Roads metropolitan area.

A New Millennium: Changes and Challenges

As the retail landscape changed in the early 2000s, Chesapeake Square adapted by welcoming new anchor tenants, such as Target and Hecht’s (which later became Macy’s in 2006).

These changes kept the mall fresh and exciting for visitors and solved challenges as the retail industry continued evolving.

Year Event
1999 Hecht’s opens
2001 Montgomery Ward closes; Target moves in
2006 Hecht’s becomes Macy’s

Weathering the Storm: Anchor Tenant Closures and Uncertain Times

The closure of several anchor tenants in the late 2000s and early 2010s signaled a problematic period for Chesapeake Square. Dillard’s, Sears, and Macy’s closed their doors, leaving vacancies and uncertainty surrounding the mall’s future.

However, the mall’s management team quickly adapted, bringing in new tenants like Burlington Coat Factory and Cinemark movie theater to fill some vacant spaces. These additions breathed new life into Chesapeake Square, providing unique entertainment options for mall visitors.

Year Event
2009 Dillard’s closes both locations
2014 Sears closes
2016 Macy’s closes

A New Direction for Chesapeake Square

In March 2022, mall owners revealed plans for a $20 million redevelopment project to revitalize the mall’s western half. This announcement came after the decision not to renew JCPenney’s lease in 2021, driven by the desire to accommodate new retailers interested in joining the mall.

The director of commercial properties for Kotarides Cos. shared that the phone had not stopped ringing with companies eager to secure a spot in the mall. As a result, mall management is focusing on redeveloping the formerly occupied by JCPenney.

Chesapeake Square Today: A Blend of Tradition and Innovation

Chesapeake Square is 717,000 square feet (66,600 m2) regional mall with approximately 40 stores and three anchor tenants: Burlington, Target, and Cinemark Theatres. The mall also features several eateries in its food court and Big Woody’s, a popular restaurant at its main entrance.

Mall’s Layout and Offerings

Chesapeake Square’s layout is designed to create a welcoming and convenient shopping experience for visitors. With a single floor, shoppers can easily navigate the mall and find their favorite stores.

USA Quiz

How many questions would you like?

Your result:
Comment based on score

The mall’s food court offers a variety of dining options for visitors to enjoy a meal or grab a quick bite while shopping. In addition, the Cinemark movie theater provides entertainment for those looking to catch the latest blockbuster films.

Community Involvement and Events

Chesapeake Square actively engages with the local community by hosting events and activities yearly. From seasonal celebrations to family-friendly entertainment, a mall is a gathering place where people can come together and create lasting memories.

By fostering a strong sense of community, the mall remains a beloved destination for residents.

The Future of Chesapeake Square: Revitalization and Growth

If the $20 million redevelopment project gets underway, Chesapeake Square is set to undergo significant changes that will reshape its identity and offerings.

The mall’s management works closely with local businesses, government officials, and residents to ensure the revitalization efforts align with the community’s needs and expectations.

Potential New Tenants and Services

While specific retailers have not yet been announced for the redeveloped areas of the mall, the interest expressed by potential new tenants suggests that Chesapeake Square will soon welcome a diverse mix of stores and services.

This may include well-known national brands, locally-owned boutiques, and innovative retailers that can cater to the ever-evolving tastes of today’s consumers.

Embracing Sustainability and Eco-Friendly Practices

As part of the redevelopment process, the mall has an opportunity to adopt environmentally-friendly practices and sustainable design principles. This could include implementing energy-efficient lighting and heating systems, using eco-friendly building materials, and creating green spaces within the mall property.

By prioritizing sustainability, Chesapeake Square can set a positive example for other businesses in the area and reduce its environmental impact.

In Conclusion: A New Chapter for Chesapeake Square

With a storied past and a promising future, Chesapeake Square is poised for a new era of growth and revitalization. The mall’s upcoming redevelopment project reflects its adaptability and commitment to meeting the needs of residents and visitors.

As Chesapeake Square continues to evolve, it remains a cherished shopping destination in the Hampton Roads metropolitan area.

Bundle your hotel + flight together to save more on your next trip! Book now at Expedia.comp565drvjpn8A99EIBAEG8ADCHCIBI website participates in the Amazon Services LLC Associates Program. This affiliate advertising program allows sites to earn advertising fees through links to Amazon products at no additional cost to you. Amazon and the Amazon logo are registered trademarks of, Inc., or its affiliates.

Add a comment

;-) :| :x :twisted: :smile: :shock: :sad: :roll: :razz: :oops: :o :mrgreen: :lol: :idea: :grin: :evil: :cry: :cool: :arrow: :???: :?: :!: