Road Trips from Gulfport, MS
Gulfport is your launchpad for Mississippi adventures, whether you're after a quick afternoon drive or a longer exploration. You've got options ranging from under an hour to over six hours, with a mix of highway and surface roads. Several routes offer proximity to national monuments and battlefields, making it easy to incorporate historical sites into your trip. Consider these drives for a spontaneous getaway.
Total Routes
20
Shortest
4h
With Parks Nearby
15
Weekend trip
20 total in this range
Rosedale, MS
6h 24m297.7 mi one way
For the longest drive on this list, Rosedale is 297.7 miles and takes 6.4 hours. This route mixes highway and surface roads and includes access to two national monuments, offering a significant historical excursion.
Tupelo, MS
5h 53m302.5 mi one way
Indianola, MS
5h 14m252.2 mi one way
Nettleton, MS
5h 46m296.8 mi one way
Amory, MS
5h 40m286.6 mi one way
This 286.6-mile drive takes 5.7 hours and mixes highway and surface roads. It boasts a drive score of 9 and includes nearby access to the Tupelo National Battlefield and Natchez Trace National Scenic Trail.
Browse by Mood
Rosedale, MS
6h 24m297.7 mi one way
Tupelo, MS
5h 53m302.5 mi one way
Indianola, MS
5h 14m252.2 mi one way
Nettleton, MS
5h 46m296.8 mi one way
Tupelo, MS
5h 53m302.5 mi one way
Indianola, MS
5h 14m252.2 mi one way
Winona, MS
4h 57m247.8 mi one way
Starkville, MS
5h 3m258.8 mi one way
When to Go
Spring
Consider drives like Amory or Rosedale in spring to explore parks and monuments with pleasant weather.
Summer
The longer highway routes to Hillsboro or Pearl are viable for summer, though be mindful of heat.
Fall
Fall offers good conditions for longer drives such as the one to Rosedale, with access to historical sites.
Winter
Shorter trips to Lyman or Nicholson are accessible year-round, with minimal weather impact on the drive.
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 Gulfport, MS city hub for all incoming and outgoing routes.