Chesapeake, VA Road Trips
Drivers starting from Chesapeake, VA have 22 mapped routes to choose from, making it a small but connected base in the Southeast. The route mix is balanced, with options ranging from 19-mile quick runs to 414-mile cross-state drives. Most routes from Chesapeake, VA head west, giving the route network a clear directional lean.
Photo: Willians Huerta
Trip Routes
50
Longest Drive
464.9 mi
Clintwood, VA
Quickest Drive
28m
Virginia Beach, VA
Plan Around Chesapeake, VA
Popular Incoming Routes
Useful if Chesapeake, VA is the arrival point and you want the strongest routes into the city first.
Continue From Chesapeake, VA
Good next legs if this city is only one stop in a longer road trip.
Trips from Chesapeake, VA
Chesapeake, VA to Claypool Hill, VA
Chesapeake, VA to Abingdon, VA
Chesapeake, VA to Tazewell, VA
Chesapeake, VA to Bluefield, VA
Chesapeake, VA to Pulaski, VA
Chesapeake, VA to Blacksburg, VA
Chesapeake, VA to Cedar Bluff, VA
Chesapeake, VA to Buchanan, VA
Chesapeake, VA to Rocky Mount, VA
Chesapeake, VA to Bridgewater, VA
Chesapeake, VA to Altavista, VA
Chesapeake, VA to Gainesville, VA
Chesapeake, VA to Amherst, VA
Chesapeake, VA to Bristow, VA
Chesapeake, VA to Lorton, VA
Chesapeake, VA to Appomattox, VA
Chesapeake, VA to Bealeton, VA
Chesapeake, VA to Aquia Harbour, VA
Driving from Chesapeake, VA
Expect an average of 228 miles and about 4h 35m behind the wheel when leaving Chesapeake, VA. There is a healthy spread of short hops, medium drives, and longer road trips to pick from. The longest mapped route runs 414 miles (7h 55m), while the shortest is just 19 miles.
Popular Destinations
Top road trip destinations from Chesapeake, VA are Claypool Hill, VA (414.2 mi, 7h 55m), Abingdon, VA (403.6 mi, 7h 36m), Tazewell, VA (401.9 mi, 7h 40m), Bluefield, VA (384.4 mi, 7h 18m), and Pulaski, VA (329.1 mi, 6h 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 228-mile trip from Chesapeake, VA, budget about $36 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 22 mapped routes leaving Chesapeake, VA and 28 routes heading into Chesapeake, VA, covering 50 total connections. Distances range from 19 to 414 miles.
The longest mapped route from Chesapeake, VA covers 414 miles and takes approximately 7h 55m. Shorter options start at just 19 miles.
The average route from Chesapeake, VA runs about 228 miles with a drive time of roughly 4h 35m. This includes both short day trips and longer multi-day drives.
At current gas prices (about $3.96/gallon for regular), the average 228-mile trip from Chesapeake, VA costs roughly $36 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 Claypool Hill, VA, Abingdon, VA, Tazewell, VA and Bluefield, VA. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.
Short Drives from Chesapeake, VA
Longer Road Trips from Chesapeake, VA
Trips to Chesapeake, VA
Clintwood, VA to Chesapeake, VA
Claypool Hill, VA to Chesapeake, VA
Coeburn, VA to Chesapeake, VA
Abingdon, VA to Chesapeake, VA
Tazewell, VA to Chesapeake, VA
Wytheville, VA to Chesapeake, VA
Pulaski, VA to Chesapeake, VA
Galax, VA to Chesapeake, VA
Cedar Bluff, VA to Chesapeake, VA
Buchanan, VA to Chesapeake, VA
Rocky Mount, VA to Chesapeake, VA
Blue Ridge, VA to Chesapeake, VA
Nearby Hubs
Other cities within driving distance of Chesapeake, VA that also have route pages.
Browse more VA road trips or choose a route from Chesapeake, VA above.