Road Trips from Chesapeake, VA
Chesapeake is your launchpad for a variety of day trips and longer excursions across Virginia. With options ranging from under 3 hours to nearly 8, you can easily hit the road for a quick escape or a more involved weekend adventure. Many routes offer direct highway driving with high drive scores, making for efficient travel. You'll also find numerous parks nearby on these routes, providing opportunities for outdoor exploration, whether you're looking for flat terrain or gently rolling hills.
Total Routes
71
Shortest
0.9h
With Parks Nearby
68
Under 2 hours
Full-day getaway
19 total in this range
Bowling Green, VA
2h 38m129 mi one way
This is your quickest option at just 2.6 hours. It's a straightforward drive, mostly on the highway, with a high drive score. You'll encounter mostly flat terrain, and it's a good choice if you want a short, easy trip with nearby park access.
Dooms, VA
3h 47m192.4 mi one way
A solid 3.8-hour drive, this route offers a similar high drive score and mostly highway profile. The terrain here is gently rolling, a bit different from the flatter options. It's a good mid-range option that gets you to a new part of the state with park access.
Hollymead, VA
3h 28m171 mi one way
Similar in length to Dooms at 3.5 hours, this trip also features a mostly highway route and a high drive score. The terrain is mostly flat, making for an easy drive. It's a comparable option to Dooms if you prefer flatter landscapes.
Ravensworth, VA
3h 45m188 mi one way
This 3.8-hour drive is another mostly highway option with a drive score of 9. The terrain is mostly flat. It's a slightly longer day trip compared to Bowling Green, offering more driving time and access to several national park areas.
West Springfield, VA
3h 41m184 mi one way
Weekend trip
43 total in this range
Bridgewater, VA
4h 17m220.1 mi one way
This is one of the longer day trips at 4.3 hours, covering 220.1 miles. The terrain is gently rolling, and the route is mostly highway with a high drive score. It's a good option if you want to venture further into Virginia for a day.
Rocky Mount, VA
5h 33m242.6 mi one way
Altavista, VA
4h 46m207.2 mi one way
This 4.8-hour trip is longer than many options, with a mixed highway and surface road profile. The terrain is mostly flat. It offers access to Appomattox Court House National Historical Park, a key distinction from other routes.
Claypool Hill, VA
7h 55m414.2 mi one way
If you're looking for a significant drive, this 7.9-hour trip covers 414.2 miles. The terrain features hilly sections with moderate elevation changes, unlike most other picks. It's a long haul, mostly highway, with a high drive score.
Rustburg, VA
4h 17m189.7 mi one way
This 4.3-hour drive is a bit longer than some, featuring a mix of highway and surface roads. The terrain is mostly flat. It provides access to Appomattox Court House National Historical Park, making it a bit different from the purely highway routes.
Long-haul ideas
6 total in this range
Richlands, VA
8h 2m418.5 mi one way
This is your longest option, an 8-hour drive covering 418.5 miles, and it's the only one where an overnight stay is recommended. It features gently rolling terrain and a mostly highway route, though with a slightly lower drive score of 8. It offers access to Booker T. Washington National Monument.
Raven, VA
8h 9m422 mi one way
Honaker, VA
8h 15m423.5 mi one way
Lebanon, VA
8h 8m424.2 mi one way
Coeburn, VA
8h 35m443.8 mi one way
Browse by Mood
Bridgewater, VA
4h 17m220.1 mi one way
Rocky Mount, VA
5h 33m242.6 mi one way
Altavista, VA
4h 46m207.2 mi one way
Bowling Green, VA
2h 38m129 mi one way
Bridgewater, VA
4h 17m220.1 mi one way
Reston, VA
4h 6m203.9 mi one way
Leesburg, VA
4h 29m218.6 mi one way
Belmont, VA
4h 22m217.4 mi one way
When to Go
Spring
Spring offers mild temperatures for exploring the numerous parks accessible via these routes, with mostly flat or gently rolling terrain ideal for outdoor activities.
Summer
Summer drives are best with the air conditioning on, especially for the longer trips. The many parks nearby provide opportunities for shade and recreation.
Fall
Autumn brings cooler weather, making the longer drives more comfortable. The varied terrain, from flat to hilly, provides scenic backdrops for leaf peeping.
Winter
Winter travel is efficient on the highway-heavy routes, though hilly terrain might present minor challenges. Park access remains, offering opportunities for brisk outdoor exploration.
Starting Somewhere Else?
Other nearby cities with their own escape planners.
Ready to plan?
Pick any destination above for full turn-by-turn directions, fuel cost, rest stops, and weather. Or visit the Chesapeake, VA city hub for all incoming and outgoing routes.