Chesapeake, VA Road Trips
Drivers starting from Chesapeake, VA have 53 mapped routes to choose from, making it a small but connected base in the Southeast. The route mix is balanced, with options ranging from 8-mile quick runs to 419-mile cross-state drives. Most routes from Chesapeake, VA head west, giving the route network a clear directional lean.
Photo: Wikimedia Commons
Trip Routes
113
Longest Drive
464.9 mi
Clintwood, VA
Quickest Drive
13m
Portsmouth Heights, 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 Richlands, VA
Chesapeake, VA to Claypool Hill, VA
Chesapeake, VA to Tazewell, VA
Chesapeake, VA to Bluefield, VA
Chesapeake, VA to Pulaski, VA
Chesapeake, VA to Woodlawn, VA
Chesapeake, VA to Blacksburg, VA
Chesapeake, VA to Buchanan, VA
Chesapeake, VA to Rocky Mount, VA
Chesapeake, VA to Edinburg, VA
Chesapeake, VA to Bridgewater, VA
Chesapeake, VA to Belmont, VA
Chesapeake, VA to New Market, VA
Chesapeake, VA to Weyers Cave, VA
Chesapeake, VA to Countryside, VA
Chesapeake, VA to Oak Grove, VA
Chesapeake, VA to Altavista, VA
Chesapeake, VA to Reston, VA
Driving from Chesapeake, VA
Expect an average of 194 miles and about 3h 58m 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 419 miles (8h 2m), while the shortest is just 8 miles.
Popular Destinations
Top road trip destinations from Chesapeake, VA are Richlands, VA (418.5 mi, 8h 2m), Claypool Hill, VA (414.2 mi, 7h 55m), 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 194-mile trip from Chesapeake, VA, budget about $30 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 53 mapped routes leaving Chesapeake, VA and 60 routes heading into Chesapeake, VA, covering 113 total connections. Distances range from 8 to 419 miles.
The longest mapped route from Chesapeake, VA covers 419 miles and takes approximately 8h 2m. Shorter options start at just 8 miles.
The average route from Chesapeake, VA runs about 194 miles with a drive time of roughly 3h 58m. This includes both short day trips and longer multi-day drives.
At current gas prices (about $3.96/gallon for regular), the average 194-mile trip from Chesapeake, VA costs roughly $30 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, Claypool Hill, VA, Tazewell, VA and Bluefield, 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.
How Much Time Do You Have?
Pick your one-way drive time and see where you can go from Chesapeake, VA.
No routes in this time range.
destinations from Chesapeake, VA.
Trips to Chesapeake, VA
Clintwood, VA to Chesapeake, VA
Coeburn, VA to Chesapeake, VA
Abingdon, VA to Chesapeake, VA
Wytheville, VA to Chesapeake, VA
Narrows, VA to Chesapeake, VA
Pulaski, VA to Chesapeake, VA
Dublin, VA to Chesapeake, VA
Galax, VA to Chesapeake, VA
Cedar Bluff, VA to Chesapeake, VA
Covington, VA to Chesapeake, VA
Buchanan, VA to Chesapeake, VA
North Shore, VA to Chesapeake, VA
Nearby Hubs
Other cities within driving distance of Chesapeake, VA that also have route pages.
Escape Planner
Where to go from Chesapeake, VA?
Curated day trips, weekend getaways, and overnight routes — grouped by how much time you have and the kind of trip you want.
Drives from Chesapeake, VA in your inbox
Monthly note with new routes, weekend drive ideas, and seasonal picks for VA. No spam, unsubscribe anytime.
Browse more VA road trips or choose a route from Chesapeake, VA above.