In the center of the Tidewater region, Chesapeake is a mostly rural city with plenty of recreational opportunities and suburbs close to the rest of Hampton Roads. It's fewer than 10 miles from downtown Norfolk, about 25 miles from Virginia Beach and just over 20 miles north of the North Carolina border. With more than 20 miles of waterways, Chesapeake caters to folks who like to spend time in kayaks, canoes and boats. There's no shortage of fishing hot spots, plus an assortment of trails for beginning and seasoned explorers alike. "I like the quietness. It feels like a rural area, but it's not. And all the land you get with your house, it just seems like a lot more space," says Geoffrey Whiteside, a Realtor with Keller Williams Town Center, who’s been living in Chesapeake for the past four years. "It's really a slow pace, to be honest with you. The area has a lot of people, but it still has that small-town feeling to it."
With a population of just over 250,000 people, Chesapeake is the second-most populous city in Virginia, the 89th-most populous U.S. city and is still growing. "A lot of people are moving to Chesapeake, and there's a lot of new development," Whiteside says. By land area, Chesapeake is the second-largest city in the state and the 17th-largest in the country. Lately, the city has also become a hot spot for business. Home to the corporate headquarters for Dollar Tree, Chesapeake has positioned itself as a business-friendly place with skilled workers and entrepreneurs. People who live here can also commute to the dense concentrations of military bases and support systems throughout Hampton Roads, including nearby Norfolk, the home port for all East Coast-based U.S. Navy aircraft carriers.
Spend the day in the great outdoors at Stumpy Lake Natural Area in Greenbrier East.
Boaters enjoy calm waters and scenic views along the Elizabeth River in Chesapeake.
Hungry goats at Bergey's petting zoo in Butts Station neighborhood of Chesapeake, Virginia
Visitors to Great Bridge explore aviation history at the Military Aviation Museum.
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Hiking at Oak Grove, kayaking in Great Dismal Swamp
Great Dismal Swamp is one of the largest remaining swamplands in the country at 113,000 acres. Lake Drummond is a 3,100-acre, natural body of water that has boat ramp access, allowing fishing for species like catfish, pickerel and sunfish. The area also features over 40 miles of trails.
Southeast of town, Chesapeake City Park is a 90-acre recreation space with picnic areas, playgrounds, a fully forested area with trails and a wide-open green space with a stage for concerts. Oak Grove Lake Park has a nearly 2-mile trail with scenic natural views throughout its layout. There are several golf courses in the city, including the Greenbrier Country Club, Chesapeake Golf Club and Battlefield Golf Club. Residents can also head to Virginia Beach for 38 miles of sandy coast along the Atlantic, or to Norfolk for its beaches on Chesapeake Bay.
Find your path in the wilds of the Great Dismal Swamp.
Enjoy scenic views and peaceful walks along the trails at Oak Grove Lake Park in Chesapeake.
Meet up with friends for a round of golf at the Eagle Creek Golf course in Hampton Roads.
Pleasant Grove West offers kayaking and fishing along the Northwest River.
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Variety of housing with a slightly higher cost of living
Chesapeake offers 14 distinct neighborhoods. Deep Creek, Greenbrier, Great Bridge and Western Branch are among the most sought after. As Chesapeake's size increases, it has to adapt to some of the growing pains that accompany urban sprawl, like strain on infrastructure, traffic and schools in some growth areas. While the cost of living in Chesapeake is nearly 11% higher than the national average, the higher prices are balanced with improving infrastructure and outdoor activities.
The median price for a single-family home is about $430,000, which is just above the state median of $425,000. Homebuyers can find older, white picket fence homes in neighborhoods like Hickory, Great Bridge or Deep Creek. There are newer home styles in neighborhoods like Culpepper Landing and Greenbrier. There are also condos and townhouses throughout the city that typically sell for a median price of $325,000.
You can find large porches in the Culpepper Landing neighborhood of Chesapeake, Virginia.
Expanded Cape Cods offer more living space for a growing family in Greenbrier East.
A contemporary brick style homes are very popular in the Western Branch neighborhood.
Split level home in the Culpepper Landing neighborhood of Chesapeake, Virginia.
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High Niche grade for Chesapeake Public Schools
Chesapeake Public Schools serves the area and earns an A-minus from Niche. The school district has several academies with specialized programs, including the Governor's STEM Academy at Grassfield High and the Science and Medicine Academy at Deep Creek High.
Tidewater Community College is the second biggest of its kind in the state. Students here can pursue a guaranteed transfer to Old Dominion University, Norfolk State University and other colleges across Virginia.
Grassfield High School is a public high school located in Chesapeake, Virginia.
Deep Creek High School is home of the Hornets in Chesapeake, Virginia.
Norfolk State University is just across the river from the Campostella neighborhood.
The Great Bridge Middle School serves grades 6-8 in the neighborhood of Great Bridge East.
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Shopping malls and seafood staples like Black Pelican Seafood Co.
The city’s major shopping and dining hubs are concentrated north of the Elizabeth River. With its location close to the Atlantic and Chesapeake Bay, the city features plenty of seafood restaurants. Greenbrier Mall, a 900,000-square-foot shopping center near the city’s border with Virginia Beach, attracts shoppers with popular retailers and dining spots like Black Pelican Seafood Co., whose original location in the Outer Banks was featured on Food Network's “Diners, Drive-Ins and Dives.” At the opposite end of town, shoppers can find Chesapeake Square, which has its own collection of popular stores and eateries like Surf Rider. Chesapeake isn't known for its nightlife and cultural scene, so residents generally travel to Norfolk or Virginia Beach for breweries and late-night clubs.
The Chesapeake Square Mall has a range of retail stores and a huge food court.
Seafood favorites at Black Pelican, a Chesapeake hotspot near Greenbrier Mall.
The Famous Surf Rider Rum Runner at Surf Rider in Chesapeake.
Casual dining with seafood classics at Surf Rider, a staple in Chesapeake, Virginia.
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Chesapeake Jubilee, Great American Food Fest
There are several popular annual events, including the Great American Food Fest, a local carnival that’s been held for over 40 years. The Chesapeake Jubilee attracts more than 35,000 visitors each year, hosting a shrimp feast, fireworks, amusement rides and games.
Locals can head north to Norfolk for live entertainment at Chrysler Hall, the Wells Theatre and the NorVA. There's also Norfolk Tides baseball in the spring and summer and Norfolk Admirals hockey games in the fall and winter.
Crime rates, flooding concerns
According to FBI data, Chesapeake's property crime rate was slightly higher than the national average. However, the city’s violent crime rate was significantly higher than national figures. Between 2020 and 2023, the violent crime rate increased by more than 8%.
According to the city’s website, most of Chesapeake is susceptible to some level of flooding from the area's many bodies of water. City officials encourage all property owners and renters to purchase flood insurance. The city is one of 1,500 communities that voluntarily take part in the Federal Emergency Management Agency's voluntary Community Rating System. As part of the program, Chesapeake works toward flood protection, which allows residents to gain discounts on insurance. The city began the program in 2015 with a Class 8 designation, but since has improved to a Class 7.
Peak hours congestion on the High Rise and Veterans Bridge
Interstate 64’s network of roads feeds into the city's north end before splintering off into U.S. Route 17 and state Route 168. Traffic on I-64 around the Interstate 464/Route 168 interchange and High Rise Bridge, crossing the Elizabeth River, can get congested during rush hours. Congestion around Veterans Bridge can also form during peak hours. Public transportation, while it exists, doesn't provide a major alternative here because of limited routes and trips. Norfolk International, about 10 miles north, is the closest airport. The Chesapeake Regional Medical Center on Battlefield Boulevard serves most of the city.
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