Road Trips from Chesapeake, VA
Chesapeake, VA is a solid launchpad for a variety of day trips, particularly if you're looking for drives with good park access. Most routes are under 4.5 hours and stick to highways, with terrain ranging from flat to gently rolling. You've got several options hitting national historical parks within a half-day's drive, plus a couple of longer hauls that might be better suited for an overnight.
Total Routes
29
Shortest
2.6h
With Parks Nearby
29
Full-day getaway
7 total in this range
Bowling Green, VA
2h 38m129 mi one way
This is your quickest option, just 2.6 hours on mostly highway. It's a straightforward drive through mostly flat terrain, perfect if you want maximum time at your destination. It offers access to Colonial National Historical Park, Fort Monroe, and George Washington Birthplace National Monument.
Dooms, VA
3h 47m192.4 mi one way
At 3.8 hours, this trip gets you into gently rolling terrain. It's similar in drive time to several other options but offers a different landscape. You'll have access to Colonial National Historical Park, Fort Monroe National Monument, and Petersburg National Battlefield.
Hollymead, VA
3h 28m171 mi one way
This 3.5-hour drive is entirely on mostly highway, making for a smooth ride. The terrain is mostly flat, and like many other Virginia destinations from Chesapeake, it provides access to Colonial National Historical Park, Fort Monroe National Monument, and Petersburg National Battlefield.
Ravensworth, VA
3h 45m188 mi one way
Covering 188 miles and taking 3.8 hours, this route offers a mostly highway experience through flat terrain. It's comparable in drive time to Dooms and Hollymead, and also grants access to Colonial National Historical Park, Fort Monroe National Monument, and Petersburg National Battlefield.
Waynesboro, VA
3h 45m190 mi one way
This 3.8-hour drive takes you into gently rolling terrain, offering a slightly different feel than the flatter routes. It's a good option for accessing Colonial National Historical Park, Fort Monroe National Monument, and Petersburg National Battlefield, similar to other nearby destinations.
Weekend trip
21 total in this range
Bridgewater, VA
4h 17m220.1 mi one way
If you're looking for a slightly longer day trip, this 4.3-hour drive through gently rolling terrain is a good choice. It's longer than many of the other options but still manageable for a single day, with access to several major historical parks.
Altavista, VA
4h 46m207.2 mi one way
This 4.8-hour drive mixes highway and surface roads, leading to mostly flat terrain. It's one of the longer day trip options and provides access to Appomattox Court House National Historical Park, Petersburg National Battlefield, and Fort Monroe National Monument.
Claypool Hill, VA
7h 55m414.2 mi one way
For a significant change of scenery, this 7.9-hour drive heads into hilly terrain with moderate elevation changes. It's a much longer haul than most other options and is the only route that doesn't list Colonial National Historical Park among its nearby parks.
Rustburg, VA
4h 17m189.7 mi one way
This 4.3-hour trip involves a mix of highway and surface roads through mostly flat terrain. It's similar in length to Bridgewater but offers a different road profile, and includes access to Appomattox Court House National Historical Park, Petersburg National Battlefield, and Fort Monroe National Monument.
Weyers Cave, VA
4h 8m212.8 mi one way
At 4.1 hours, this drive is mostly highway with gently rolling terrain. It's a solid day trip option that brings you closer to the western side of Virginia and provides access to Fort Monroe National Monument, Colonial National Historical Park, and Petersburg National Battlefield.
Long-haul ideas
Browse by Mood
Bridgewater, VA
4h 17m220.1 mi one way
Altavista, VA
4h 46m207.2 mi one way
Bowling Green, VA
2h 38m129 mi one way
Claypool Hill, VA
7h 55m414.2 mi one way
Bridgewater, VA
4h 17m220.1 mi one way
New Market, VA
4h 35m217.3 mi one way
Waynesboro, VA
3h 45m190 mi one way
Luray, VA
4h 37m217.9 mi one way
When to Go
Spring
Spring offers pleasant driving conditions through flat and gently rolling terrain, ideal for visiting the numerous historical parks accessible from Chesapeake.
Summer
Summer road trips are well-suited for the mostly highway routes, allowing for efficient travel to destinations with historical park access.
Fall
Fall foliage could enhance the gently rolling terrain on longer drives, making the 4-hour plus trips more scenic.
Winter
Winter travel is best suited for the shorter, mostly highway routes, as terrain can be less predictable in hilly areas.
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.