6 Picturesque Small Towns in Mississippi for a Weekend Retreat

Let’s face it: 23 million tourists can’t be wrong. That’s the number of annual visitors who make the journey to Mississippi from around the globe for fun family vacations, day trips, and romantic weekend getaways, all of them drawn by the Magnolia State’s rich blend of cultural and historic attractions, as well as its beautiful scenery.

From the coastal beauty of Bay St Louis on the Gulf of Mexico to the quaint historic streets of Port Gibson, from the many colorful festivals in Canton to the musical heritage of Cleveland, and from the beaches of Ocean Springs to the natural beauty of Hattiesburg, Mississippi’s cozier communities are simply brimming with character and that pervasive Southern hospitality. Find out more with these six picturesque small towns in Mississippi that are perfect for a weekend retreat.

Ocean Springs

Ocean Springs is located on the Mississippi Gulf Coast and is a picturesque town that oozes Southern charm. It’s also increasingly making a name for itself for its vibrant arts community, with weekend visitors flocking to attractions like the Walter Anderson Museum of Art. This state-of-the-art attraction celebrates the works of renowned 20th-century artist Walter Inglis Anderson, whose depictions of local flora and fauna have earned national acclaim.

The creative juices will also be triggered by a visit to Shearwater Pottery. Founded by Anderson's brother, Peter Anderson, it showcases unique ceramics that reflect Ocean Spring’s attractive coastal scenery. Weekend visitors interested in spending time outdoors will want to visit the Gulf Islands National Seashore for its beaches, marshes, and forests, while the Fontainebleau Nature Trail presents an easy hike with great views and wildlife. Come bedtime, check out the best rates at the centrally located Springs Hotel and The Inn of Ocean Springs.

Port Gibson

Port Gibson is another great place to visit in Mississippi for a weekend retreat. Famously described by Union General Ulysses S. Grant as "the town too beautiful to burn," you can find out more about Port Gibson’s Civil War experiences at Grand Gulf Military State Park. The park features fortifications, a museum, and several historical structures that provide insights into the area's strategic importance during this chaotic period in American history.

The Windsor Ruins attraction is another must-visit. Here, visitors can explore the remains of this once-opulent antebellum mansion, including its surviving columns. Natural attractions like the Mississippi River also add to Port Gibson’s appeal and can be explored from accommodation options, including the cozy Isabella Bed and Breakfast and the Collina House.

Canton

Canton is located just off the I-55 a few miles north of the state capital of Jackson, making it a perfect destination for a weekend getaway. Known as the "City of Lights" for the more than 200,000 twinkling white lights adorning its pretty Courthouse Square during its Christmas Festival, it’s especially fun to visit during the Canton Flea Market Arts and Craft Show. Held in May and again in October, this popular event attracts many visitors (so be sure to plan ahead if accommodations are needed!).  

Those interested in cinematic history will want to include the Canton Film Museums on their Mississippi travel itinerary. Highlights include displays relating to movies like O Brother, Where Art Thou?, which was shot here. Great places to stay in Canton are also plentiful and include big brand names like the Hampton Inn Canton and Holiday Inn Express & Suites Canton.

Bay St Louis

While Bay St Louis needs little introduction to Mississippians, outsiders are often surprised to learn of the amazing beaches and artsy vibe the town boasts. Located on the Gulf Coast of Mississippi and only an hour’s drive from New Orleans, the town's waterfront is another key attraction and provides endless opportunities for fishing, boating, or simply enjoying the Gulf Coast's natural beauty…all just steps away from some of the best beaches in the region.

If possible, try to book a place to stay as close as possible to Old Town Bay St Louis. In addition to its many boutique shops and art galleries, this trendy district is famous for its walkable, pedestrian-friendly streets. Accommodation options are plentiful and include the Abode Guest House and Carroll House Bed & Breakfast, both within walking distance of downtown Bay St Louis.

Cleveland

Cleveland is a great spot to visit for those wanting to explore the musical legacy of the Mississippi Delta area. Well-known for its significant contributions to the blues genre, Cleveland is home to the Grammy Museum Mississippi, a landmark attraction that celebrates the state's musical legacy through interactive exhibits, educational programs, and displays relating to the history of the Grammys.

Cleveland is also known as a hub for artists, as seen in the Mathew-Sanders Sculpture Garden located at Delta State University. Delta State University also hosts the annual Octoberfest, which is another great time to visit, especially if combined with a stay at trendy places like Lyric Hotel West End or Cotton House.

Hattiesburg

Hattiesburg’s location at the crossroads of four major US highways, as well as its proximity to the state border with Alabama, is a big plus for weekend travelers and has led to its being nicknamed "Hub City.” It’s an especially popular destination for military buffs for its being the home of the African American Military History Museum. Housed in a historic USO (United Services Organization) building, this fascinating attraction gives a deep dive into the contributions of African American soldiers throughout U.S. military history.

For nature enthusiasts, Paul B. Johnson State Park on Geiger Lake provides opportunities for camping, fishing, hiking, picnicking, and other fun things to do on the weekend. Need a place to stay? Check out Hotel Indigo Hattiesburg and avid hotel Hattiesburg West, both members of the IHG hotel group.

For those wanting to drill down and get to know the Magnolia State, exploring Mississippi's small towns offers a captivating and authentic journey through the heart of the South. From Ocean Springs' artistic shores​​ to the historic ambiance of Port Gibson, each of these towns provides a great opportunity to enjoy a fun weekend retreat in Mississippi. With a rich blend of cultural attractions, natural beauty, and Southern hospitality, Mississippi's cozier communities promise memorable adventures for all who venture there.