30 days in Mississippi Itinerary

30 days in Mississippi Itinerary

Created using Inspirock Mississippi trip planner
Make it your trip
Fly
1
Tupelo
— 3 nights
Drive
2
Starkville
— 3 nights
Drive
3
Jackson
— 5 nights
Drive
4
Hattiesburg
— 4 nights
Drive
5
Gulfport
— 4 nights
Drive
6
Natchez
— 6 nights
Drive
7
Indianola
— 1 night
Drive
8
Clarksdale
— 3 nights
Fly

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Tupelo — 3 nights

Tupelo is the county seat and the largest city of Lee County, Mississippi. Step off the beaten path and head to Rowan Oak and Tombigbee State Park. Change things up with these side-trips from Tupelo: The Crossroads Museum (in Corinth), Historic Downtown Square (in Oxford) and Tishomingo State Park (in Tishomingo). The adventure continues: brush up on your military savvy at Tupelo Veteran's Museum, stroll around Ballard Park, take in the history at Brice's Crossroads National Battlefield, and stroll through Tanglefoot Trail.

For maps, more things to do, traveler tips, and more tourist information, read our Tupelo tour itinerary planner.

New York City to Tupelo is an approximately 6.5-hour flight. You can also drive; or take a bus. Traveling from New York City to Tupelo, you'll gain 1 hour due to the time zone difference. When traveling from New York City in November, plan for a bit warmer days in Tupelo, with highs around 64°F, while nights are about the same with lows around 41°F. Wrap up your sightseeing on the 4th (Thu) to allow time to drive to Starkville.
Parks · Historic Sites · Museums · Nature
Side Trips

Starkville — 3 nights

Starkville is a city in and the county seat of Oktibbeha County, Mississippi, United States. Explore hidden gems such as Mississippi State University and Cobb Museum of Archaeology. Venture out of the city with trips to Philadelphia (Williams Brothers & Silver Star Casino), Waverley Plantation Mansion (in West Point) and Columbus (Friendship Cemetery & Lake Lowndes State Park). There's still lots to do: tee off at Dancing Rabbit Golf Club and try to win big at Pearl River Resort and Casino.

To see maps, traveler tips, and other tourist information, refer to the Starkville trip planner.

Traveling by car from Tupelo to Starkville takes 1.5 hours. In November in Starkville, expect temperatures between 63°F during the day and 39°F at night. Wrap up your sightseeing on the 7th (Sun) to allow time to travel to Jackson.
Historic Sites · Fun & Games · Casinos · Museums
Side Trips

Jackson — 5 nights

Jackson, officially the City of Jackson, is the capital city and largest urban center of the U.S. state of Mississippi. Step off the beaten path and head to Mississippi State Capitol and Jesse Brent Lower Mississippi River Museum and Interpretive Center. Get out of town with these interesting Jackson side-trips: Vicksburg (The Old Depot Museum, Old Court House Museum - Eva W. Davis Memorial, &more) and Mississippi Petrified Forest (in Flora). There's much more to do: learn more about the world around you at Mississippi Museum of Natural Science, explore the world behind art at Mississippi Museum of Art, look for gifts at Mississippi Crafts Center, and admire the landmark architecture of Old Capitol Museum.

For reviews, ratings, photos, and tourist information, use the Jackson journey builder app.

Traveling by car from Starkville to Jackson takes 2.5 hours. Plan for somewhat warmer nights when traveling from Starkville in November since evenings lows in Jackson dip to 46°F. Finish your sightseeing early on the 12th (Fri) so you can travel to Hattiesburg.
Museums · Historic Sites · Shopping · Outdoors
Side Trips

Hattiesburg — 4 nights

Hattiesburg is a city in the U.S. state of Mississippi, primarily in Forrest County (where it is the county seat) and extending west into Lamar County. You'll explore the less-touristy side of things at Mississippi Armed Forces Museum and Paul B. Johnson State Park. You'll find plenty of places to visit near Hattiesburg: Red Bluff (in Foxworth), Meridian (The Dentzel Carousel, Bonita Lakes Park, &more) and Laurel (Landrum's Homestead & Village & Lauren Rogers Museum of Art). There's lots more to do: meet the residents at Hattiesburg Zoo, explore the landscape on two wheels at Longleaf Trace, and stop by The Lucky Rabbit.

To see where to stay, photos, traveler tips, and more tourist information, read our Hattiesburg travel route planner.

Drive from Jackson to Hattiesburg in 2 hours. In November in Hattiesburg, expect temperatures between 71°F during the day and 44°F at night. Finish up your sightseeing early on the 16th (Tue) so you can go by car to Gulfport.
Parks · Museums · Nature · Outdoors
Side Trips

Gulfport — 4 nights

Gulfport is the second largest city in Mississippi after the state capital, Jackson. Explore hidden gems such as Lynn Meadows Discovery Center and Biloxi Bay Bridge. You'll find plenty of places to visit near Gulfport: Ocean Springs (Mississippi Vietnam Veterans Memorial & Walter Anderson Museum of Art) and Lazy Magnolia Brewing Company (in Kiln). There's still lots to do: head outdoors with Outdoor Activities, take a leisurely stroll along Bay Saint Louis Beach, make a trip to Friendship Oak, and examine the collection at Mississippi Coast Model Railroad Museum.

For photos, other places to visit, where to stay, and more tourist information, read our Gulfport day trip planning app.

Getting from Hattiesburg to Gulfport by car takes about 1.5 hours. Traveling from Hattiesburg in November, expect a bit warmer with lows of 50°F in Gulfport. Finish up your sightseeing early on the 20th (Sat) so you can go by car to Natchez.
Museums · Breweries & Distilleries · Historic Sites · Childrens Museums
Side Trips

Natchez — 6 nights

Natchez is the county seat and only city of Adams County, Mississippi, United States. You'll explore the less-touristy side of things at Bluff Park and Natchez National Cemetery. Explore the numerous day-trip ideas around Natchez: Port Gibson (Grand Gulf Military Park & Windsor Ruins). Spend the 26th (Fri) exploring nature at Natchez National Historical Park. There's much more to do: admire the landmark architecture of First Presbyterian Church, contemplate the long history of Dunleith Historic Inn, cruise along The Natchez Trace Parkway, and make a trip to Choctaw Hall.

For photos, other places to visit, where to stay, and other tourist information, read our Natchez trip itinerary planning website.

Getting from Gulfport to Natchez by car takes about 4 hours. Other options: do a combination of taxi, bus, train, and car; or do a combination of bus, train, and car. November in Natchez sees daily highs of 68°F and lows of 46°F at night. Finish up your sightseeing early on the 26th (Fri) so you can travel to Indianola.
Historic Sites · Parks · Nature · Outdoors
Side Trip

Indianola — 1 night

Indianola is a city in Sunflower County, Mississippi, United States, in the Mississippi Delta. On the 27th (Sat), examine the collection at B.B. King Museum and Delta Interpretive Center, examine the collection at Jim Henson Exhibit, and then see the interesting displays at Highway 61 Blues Museum.

To see ratings, where to stay, other places to visit, and more tourist information, go to the Indianola online driving holiday planner.

Traveling by car from Natchez to Indianola takes 3 hours. In November in Indianola, expect temperatures between 65°F during the day and 43°F at night. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Clarksdale.
Museums
Side Trip

Clarksdale — 3 nights

Clarksdale is a city in Coahoma County, Mississippi, and seat of the county. You'll explore the less-touristy side of things at Cat Head Delta Blues & Folk Art and The Crossroad. Change things up with these side-trips from Clarksdale: Tunica (Sam's Gambling Hall & Tunica Museum), Emmett Till Historic Intrepid Center (in Glendora) and Cleveland (GRAMMY Museum Mississippi & Dockery Farms). There's still lots to do: contemplate the waterfront views at Grenada Lake and view the masterpieces at Stan Streets Hambone Art Gallery.

To find more things to do, ratings, photos, and other tourist information, refer to the Clarksdale trip itinerary maker website.

Traveling by car from Indianola to Clarksdale takes 1.5 hours. In November, daytime highs in Clarksdale are 62°F, while nighttime lows are 42°F. Wrap up your sightseeing on the 30th (Tue) early enough to fly back home.
Museums · Shopping · Fun & Games · Casinos
Side Trips

Mississippi travel guide

3.4
Casinos · Historic Sites · History Museums
The Magnolia State
Still relatively unspoiled by mass tourism, Mississippi epitomizes rich history and offers warm hospitality to those who vacation here. The Mississippi River forms most of its western border, so it's no surprise that this mighty waterway shapes the lives of people calling the "Magnolia State" their home. The river influences everything from the food they eat to the music they listen to. Perhaps the easiest way to discover Mississippi is to take a drive on the 715 km (444 mi) long national parkway, which follows a route used since pre-colonial times that's famous for its scenic beauty and attractions of historical interest. At the end of the parkway sits a town packed with nearly 600 antebellum homes.