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Chesapeake, VA Road Trips

Drivers starting from Chesapeake, VA have 29 mapped routes to choose from, making it a small but connected base in the Southeast. The route mix is balanced, with options ranging from 129-mile quick runs to 419-mile cross-state drives. Most routes from Chesapeake, VA head west, giving the route network a clear directional lean.

Downtown Chesapeake, VA, VA

Photo: Wikimedia Commons

Trip Routes

29

Longest Drive

418.5 mi

Richlands, VA

Quickest Drive

2h 38m

Bowling Green, VA

Plan Around Chesapeake, VA

Trips from Chesapeake, VA

Driving from Chesapeake, VA

Expect an average of 253 miles and about 5h 4m behind the wheel when leaving Chesapeake, VA. This is long-haul territory. Most routes stretch past the 250-mile mark, so pack snacks and plan fuel stops. The longest mapped route runs 419 miles (8h 2m), while the shortest is just 129 miles.

Popular Destinations

Top road trip destinations from Chesapeake, VA are Richlands, VA (418.5 mi, 8h 2m), Bristol, VA (418.5 mi, 7h 52m), Claypool Hill, VA (414.2 mi, 7h 55m), Tazewell, VA (401.9 mi, 7h 40m), and Bluefield, VA (384.4 mi, 7h 18m). Most destinations stay within the same state, perfect for exploring the local region thoroughly.

Planning & Costs

Regular gas in VA currently averages around $3.96 per gallon. For the typical 253-mile trip from Chesapeake, VA, budget about $40 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.

Most routes head west — leaving in the morning keeps the sun behind you for a more comfortable drive. Most trips take a half-day, so a morning start gets you there in time for lunch or an afternoon of exploring.

Frequently Asked Questions

There are 29 mapped routes leaving Chesapeake, VA and 0 routes heading into Chesapeake, VA, covering 29 total connections. Distances range from 129 to 419 miles.

The longest mapped route from Chesapeake, VA covers 419 miles and takes approximately 8h 2m. Shorter options start at just 129 miles.

The average route from Chesapeake, VA runs about 253 miles with a drive time of roughly 5h 4m. This includes both short day trips and longer multi-day drives.

At current gas prices (about $3.96/gallon for regular), the average 253-mile trip from Chesapeake, VA costs roughly $40 in fuel one way, based on 25 MPG. Your actual cost depends on your vehicle's efficiency.

The most popular road trip destinations from Chesapeake, VA include Richlands, VA, Bristol, VA, Claypool Hill, VA and Tazewell, VA. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.

Chesapeake, VA by the Numbers

Recent demographic snapshot from the US Census Bureau's American Community Survey.

Population

251,153

Median Income

$94,189

Median Home Value

$359,100

Median Age

37.7

Source: US Census Bureau ACS 5-year (public domain). See our methodology for details.

Chesapeake, VA at a Glance

Founded

1963

Elevation

10 ft

Area

351 mi²

Sister Cities

Joinville

Notable People from Chesapeake, VA

A sampling of people born in Chesapeake, VA.

Grant Holloway

Grant Holloway

1997

American athlete

Alonzo Mourning

Alonzo Mourning

1970

American basketball player

Michael Copon

Michael Copon

1982

American actor, model, producer and singer

Jay Pharoah

Jay Pharoah

1987

American actor and comedian

Mike Scott

Mike Scott

1988

American basketball player (born 1988)

Randy Forbes

Randy Forbes

1952

American politician

Quanitra Hollingsworth

Quanitra Hollingsworth

1988

Turkish basketball player (born 1988)

Briante Weber

Briante Weber

1992

American basketball player

Magnum T.A.

Magnum T.A.

1959

American professional wrestler

Landmarks & Historic Sites

Attractions and heritage-registered places located in Chesapeake, VA.

Dismal Swamp Canal

Dismal Swamp Canal

canal in Virginia, United States of America

Historic Civil Engineering Landmark Virginia Historic Landmark
Albemarle and Chesapeake Canal

Albemarle and Chesapeake Canal

canal in Chesapeake, Virginia

Virginia Historic Landmark National Register of Historic Places listed place
South Norfolk Historic District

South Norfolk Historic District

historic district in Virginia, United States

Virginia Historic Landmark National Register of Historic Places listed place
Sunray Agricultural Historic District

Sunray Agricultural Historic District

historic district in Virginia, United States

Virginia Historic Landmark National Register of Historic Places listed place

City data from Wikidata (Q49222), available under CC0. Photos from Wikimedia Commons under their respective licenses. See our methodology for details.

Traveler Guide to Chesapeake, VA

Chesapeake is a town of 245,000 people (2019) in the Hampton Roads region of Eastern Virginia. Chesapeake is a diverse city in which a few urban areas are located; it also has many square miles of protected farmland, forests, and wetlands, including a substantial portion of the Great Dismal Swamp National Wildlife Refuge.

1 Great Bridge Battlefield & Waterways Historic Park. (updated Oct 2019) 2 Chesapeake Arboretum. (updated Oct 2019)

Cinema Cafe, 1864 Edinburgh Ln. Movie watching with menu service.

Broken Egg Bistro, 501 Kempsville Rd, ☏ +1 757-410-8515. Consistently voted "best breakfast in Chesapeake," Broken Egg Bistro turns out some of the best breakfast in all of Hampton Roads. Also has a great lunch menu with a large selection of speciality sandwiches and burgers.

1 Norfolk Marriott Chesapeake, 725 Woodlake Dr, ☏ +1 757-523-1500. Check-in: 3PM, check-out: noon. Holiday Inn Express & Suites Chesapeake, 721 Conference Center, ☏ +1 757-698-4400. Chesapeake Staybridge Suites, 709 Woodlake Dr, ☏ +1 757 4202-525. Specializing in the extended stay experience, this all suites hotel is pet-friendly. Courtyard Chesapeake Greenbrier, 1562 Crossways Boulevard, ☏ +1 757 420-1700, fax: +1 757 420-1939. Fairfield Inn Chesapeake, 1560 Crossways Boulevard, ☏ +1 757 420-1300, fax: +1 757 366-0608. Hyatt Place Chesapeake/Greenbrier, 709 Eden Way North, ☏ +1 757 312-0020. Rooms with free Wi-Fi, large work space, refrigerator, TV. Guests have access to free parking, free breakfast, indoor pool and fitness center. $122. Delta Hotels Chesapeake Norfolk, 725 Woodlake Drive. Chesapeake's only full-service hotel boasts a sophisticated environment for successful corporate events and high-speed Internet access, business centers, Express Check-in/Check-out, and concierge services. Residence Inn Chesapeake Greenbrier, 1500 Crossways Blvd, ☏ +1 757 502-7300, fax: +1 757 502-7301.

Like with most of the Hampton Roads area, it is difficult to get around Chesapeake without the use of a car. Hampton Roads Transit does service some areas of the city, which can be found here HRT. There are numerous road systems that are available to get in and out of Chesapeake. The most popular of these is the Hampton Roads belt way, which consists of I-64 (on the east side of the city), I-664 (on the west side of the city), and I-464 on the Norfolk/Chesapeake border. US-13/460/58 is the system of roads that connect Chesapeake to Suffolk and provide service to other parts of the state. US-13 connects to Northeastern North Carolina; US-460 connects to Petersburg; US-58 connects to Emporia and Southside Virginia. VA-168, also known as the Chesapeake Express way (or bypass to locals) provides service to south Chesapeake and to the Outer Banks of North Carolina and is the only toll road in the Hampton Roads area. The toll for the Express way is located on the border between Virginia and North Carolina, travellers are not obligated to pay the toll unless they stay on the road that goes through the toll station. The Hampton roads area, especially in Chesapeake, is known for the numerous bridges and tunnels, which can be confusing to anyone not familiar with the local roads. Chesapeake has several bridges over the Elizabeth River, and it is crucial to know which one to take in order to avoid long delays or getting lost.

Travel tips adapted from Chesapeake on Wikivoyage, licensed CC BY-SA 4.0. Content summarized; visit the source for the full article. See our methodology for how we use it.

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