6 Most Overlooked Mississippi Towns For 2025

Often skipped in favor of larger city destinations like Jackson and Biloxi, Mississippi’s most overlooked towns have plenty to offer curious travelers. Not only do these communities in the Magnolia State boast travel experiences that their larger neighbors can’t replicate, they’re also among the best destinations for a truly authentic taste of that famous Southern hospitality.

If you’re looking for ideas and inspiration concerning vacationing in the Deep South, these all-too-often snubbed Mississippi towns are ideal places to visit in 2025.

Cleveland

Cleveland’s position in the heart of the Mississippi Delta led to its becoming the crossroads of blues music history. Music is celebrated everywhere here. Start exploring at the GRAMMY Museum Mississippi, the only such museum of its kind outside of Los Angeles. It’s a big place, so be sure to allocate plenty of time to explore its interactive exhibits on Mississippi's musical influences on legends such as B.B. King, Elvis Presley, and Faith Hill.

Also on the Delta State University campus, the Bologna Performing Arts Center features touring Broadway productions, ballet performances, symphony orchestras, and internationally recognized musicians encompassing almost all genres. The Martin and Sue King Railroad Heritage Museum, housed in a restored 1918 depot, is another historic attraction and documents the Illinois Central Railroad's role in the Great Migration, when millions of African Americans moved north between 1910 and 1970.

Port Gibson

Earning its reputation as "The Town Too Beautiful to Burn" when Union General Ulysses S. Grant spared it from destruction during the Civil War’s 1863 Vicksburg Campaign, Port Gibson is a Southern gem that must be visited to be believed. Boasting more antebellum architecture per capita than almost any other town in Mississippi, charming Church Street alone contains eight structures listed on the National Register of Historic Places, including First Presbyterian Church with its famous 10-foot-tall golden hand atop the steeple (its index finger has been pointing heavenward since 1859).

Not so lucky, however. The Windsor Ruins features 23 tall Corinthian columns, all that remains of what was once the largest antebellum mansion in Mississippi. Despite burning down in 1890, the columns survived intact and created a ghostly monument to the former grandeur of the Old South. Other highlights include the original Claiborne County Courthouse, built in 1845 in Greek Revival style; be sure to take a tour and view its elegant pressed-tin ceilings.

Holly Springs

Holly Springs is another charming small Mississippi town worth visiting in 2025 for its intact antebellum architecture. Despite having changed hands countless times during the Civil War (you can still see bullet holes in several buildings), much of the architecture in Holly Springs’ historic district predates 1860, including the impressive Montrose mansion, built in 1858 and now a must-see museum. It and several private homes open up each April for public viewing as part of the Holly Springs Pilgrimage (plans are already underway for the 2026 edition of the popular event).

Other highlights of a visit to Holly Springs include Rust College, founded in 1866 as one of the first historically black colleges in Mississippi, and the Ida B. Wells-Barnett Museum on Randolph Street, which commemorates the journalist and civil rights activist born into slavery here in 1862. The museum occupies the restored Bolling-Gatewood House, built in 1858, with exhibits documenting the anti-lynching campaign that helped launch America’s civil rights movement.

Woodville

One of Mississippi's oldest chartered towns, Woodville, was established in 1811 and is a delight to explore. TheWilkinson County Courthouse, built in 1903, sits in the picturesque town square and is notable for its unique copper dome, something townsfolk will proudly tell you can be seen from miles away. The courthouse lawn contains the state's oldest Confederate monument, erected in 1871 when Reconstruction governments controlled most of Mississippi. It was also here that Andrew Jackson reviewed troops before the Battle of New Orleans in 1815.

The nearby Rosemont Plantation, Jefferson Davis's childhood home, can be toured and features original furnishings, including the bed where the future Confederate president was born in 1808. Carry on a little further from the downtown area, and you’ll find yourself in the Clark Creek Natural Area. Here, you’ll find Mississippi's highest waterfalls, with drops reaching 50 feet, an especially impressive sight after heavy rain.

Ocean Springs

Located on Mississippi's Gulf Coast, Ocean Springs is only separated from Biloxi by a narrow bay. Yet despite its proximity to the state’s fourth-largest city, Ocean Springs (aka, “The City of Discovery”) has managed to preserve a small-town appeal that sets it apart from its casino-dominated neighbor. Established in 1699 when the French built Fort Maurepas nearby, the area became the region’s first permanent European settlement.

These days, Ocean Springs is best known for its active, creative community. In addition to arts-focused events like the Peter Anderson Arts & Crafts Festival in November (an event that attracts upwards of 150,000 visitors and some 400 artists and craftspeople), the Walter Anderson Museum of Art is another excellent excuse to plan a visit. Set within the town’s increasingly popular Washington Avenue cultural district, the museum displays works by the acclaimed artist, as well as the restored cottage where he lived and worked.

Shearwater Pottery, founded by Anderson's brothers in 1928, is another must-see and produces handcrafted pieces for collectors and souvenir hunters alike. Natural landmarks include the Mississippi Sandhill Crane National Wildlife Refuge, a crucial habitat for the endangered Mississippi sandhill crane (guided tours are available).

Bay St. Louis

For a complete change of scenery, head to Bay St. Louis for its wonderful Gulf Coast setting. Despite being severely impacted by Hurricane Katrina in 2005 (and being just 50 miles from New Orleans), the town has managed to preserve much of its original historic character. Start your self-guided walking tour in Old Town Bay St. Louis, a delightful area of heritage buildings lining Main Street and Beach Boulevard. Here you’ll find pretty Sycamore House, a restored 1880s cottage that’s now a popular restaurant, and Maggie May's, a funky art gallery featuring works by local artists.

The Alice Moseley Folk Art Museum on Main Street is another must-see for culture vultures. It displays a series of paintings depicting Mississippi life through the self-taught artist's perspective. Be sure also to check out the 2025 schedule at the Bay St. Louis Little Theatre, established in 1946 and presenting several productions annually. Round off your visit with time on Bay St. Louis Beach, a charming spot to sit and watch the world go by… on land and water.

If you’ve not yet explored Mississippi, these six towns ideally introduce the Magnolia State’s unique character. Boasting authentic travel experiences that are all too often overlooked by tourists, these communities have managed to resist the temptation to homogenize their offerings and instead opt to preserve their distinct Southern vibe. Please take a read of our choice of these six often bypassed small Mississippi towns and try to squeeze one or two into your 2025 travel itineraries.