Chesapeake, VA Road Trips

Sitting in the Southeast, Chesapeake, VA is a well-connected starting point with 19 trip routes mapped and ready to explore. The route mix is balanced, with options ranging from 21-mile quick runs to 404-mile cross-state drives. Routes from Chesapeake, VA spread mainly west and north, covering a wide geographic range.

Photo: Willians Huerta

Trip Routes

19

Longest Drive

432.9 mi

Clintwood, VA

Quickest Drive

24m

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.

Clintwood, VA to Chesapeake, VA 432.9 mi · 7h 49m Claypool Hill, VA to Chesapeake, VA 384.4 mi · 6h 43m Abingdon, VA to Chesapeake, VA 374.4 mi · 6h 22m Wytheville, VA to Chesapeake, VA 317.8 mi · 5h 38m

Continue From Chesapeake, VA

Good next legs if this city is only one stop in a longer road trip.

Chesapeake, VA to Abingdon, VA 403.6 mi · 7h 36m Chesapeake, VA to Pulaski, VA 329.1 mi · 6h 18m Chesapeake, VA to Bridgewater, VA 220.1 mi · 4h 17m Chesapeake, VA to Gainesville, VA 192.5 mi · 3h 56m

Trips from Chesapeake, VA

Chesapeake, VA to Abingdon, VA

403.6 mi 7h 36m

Chesapeake, VA to Pulaski, VA

329.1 mi 6h 18m

Chesapeake, VA to Bridgewater, VA

220.1 mi 4h 17m

Chesapeake, VA to Gainesville, VA

192.5 mi 3h 56m

Chesapeake, VA to Newport News, VA

33.2 mi 37m

Chesapeake, VA to Virginia Beach, VA

20.6 mi 24m

Driving from Chesapeake, VA

The typical drive from Chesapeake, VA covers about 200 miles and takes around 3h 51m. There is a healthy spread of short hops, medium drives, and longer road trips to pick from. The longest mapped route runs 404 miles (7h 36m), while the shortest is just 21 miles.

Popular Destinations

Top road trip destinations from Chesapeake, VA are Abingdon, VA (403.6 mi, 7h 36m), Pulaski, VA (329.1 mi, 6h 18m), Bridgewater, VA (220.1 mi, 4h 17m), Gainesville, VA (192.5 mi, 3h 56m), and Newport News, VA (33.2 mi, 37m). 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 200-mile trip from Chesapeake, VA, budget about $31 in fuel one way, assuming 25 MPG. Longer hauls and premium fuel will cost proportionally more.

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

Frequently Asked Questions

There are 6 mapped routes leaving Chesapeake, VA and 13 routes heading into Chesapeake, VA, covering 19 total connections. Distances range from 21 to 404 miles.

The longest mapped route from Chesapeake, VA covers 404 miles and takes approximately 7h 36m. Shorter options start at just 21 miles.

The average route from Chesapeake, VA runs about 200 miles with a drive time of roughly 3h 51m. This includes both short day trips and longer multi-day drives.

At current gas prices (about $3.96/gallon for regular), the average 200-mile trip from Chesapeake, VA costs roughly $31 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 Abingdon, VA, Pulaski, VA, Bridgewater, VA and Gainesville, VA. Each route page has detailed drive times, fuel estimates, stop suggestions, and turn-by-turn directions.