Southside vs. the Peninsula: Hampton Roads Cities Explained

Two Sides of the Harbor

Hampton Roads is named for the harbor at the mouth of the Chesapeake Bay, and the water shapes daily life here. Locals divide the region into the Southside and the Peninsula. Which side you live on decides which bridge or tunnel you use to get to work, so it is usually the first thing to settle when you are house hunting.

• Southside: Norfolk, Virginia Beach, Chesapeake, Portsmouth and Suffolk.
• Peninsula: Hampton, Newport News, Poquoson, Williamsburg, and York and James City counties.

The crossings

• Hampton Roads Bridge-Tunnel (I-64) connects Hampton and Newport News with Norfolk and Virginia Beach. No toll. Its first tube opened in 1957 and the second in 1976.
• Monitor-Merrimac Memorial Bridge-Tunnel (I-664) connects Newport News and Hampton with Suffolk and Chesapeake. No toll, opened 1992, and it carries roughly half the traffic of the HRBT.
• James River Bridge (Routes 17/258/32) links Newport News with Isle of Wight County and is Virginia's longest state-maintained bridge at 4.5 miles. No toll.
• Downtown Tunnel (I-264) and Midtown Tunnel (Route 58) connect Norfolk and Portsmouth within the Southside. Both are tolled.

Source: Virginia Department of Transportation, as of September 2026.

The Cities, Side by Side

Land areas come from the U.S. Census Bureau's 2024 Gazetteer and populations are July 2025 Census estimates.

Southside

• Norfolk - 53 square miles of land, about 231,000 residents. The downtown waterfront holds Nauticus and the Battleship Wisconsin; Ocean View faces the Chesapeake Bay.
• Virginia Beach - 245 square miles of land and even more water, about 454,000 residents. Its boardwalk runs about three miles along the oceanfront.
• Chesapeake - 339 square miles of land, about 255,000 residents. Part of the Great Dismal Swamp National Wildlife Refuge, nearly 113,000 acres with the 3,108-acre Lake Drummond, lies here.
• Suffolk - 399 square miles, the largest land area of any Virginia city, with about 105,000 residents. The refuge's main visitor entrance is on Desert Road.
• Portsmouth - 33 square miles, about 97,000 residents. Olde Towne, its first historic district, covers more than twenty blocks along the Elizabeth River.

Peninsula

• Hampton - 52 square miles of land, about 137,000 residents. Fort Monroe National Monument sits at Old Point Comfort, and NASA Langley Research Center dates to 1917.
• Newport News - 69 square miles, about 183,000 residents. The Mariners' Museum and Park includes the USS Monitor Center and the Noland Trail.
• Poquoson - 15 square miles of land and 63 of water, about 13,000 residents, next to the Plum Tree Island refuge.
• Williamsburg - 9 square miles, about 16,000 residents. Colonial Williamsburg's historic area covers 301 acres.
• York County (about 71,000) and James City County (about 83,000) border Williamsburg; Colonial National Historical Park connects Historic Jamestowne and Yorktown Battlefield by the 23-mile Colonial Parkway.

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