11 of the Coziest Mississippi Towns for Your Next Weekend Vacation

There’s More Than Jackson and Biloxi in MS

The Magnolia State’s got some seriously charming small towns that deserve your attention, especially if you’re into that laid-back Southern atmosphere. Here are 11 of our favorites.

Ocean Springs

Ocean Springs was founded in 1699 as the first permanent French settlement in Louisiana, but this quiet fishing village soon became a hub for artists in the 1900s.

The Davis Bayou Area offers fantastic kayaking through cypress-filled waters. Drop by the Farmer’s Market on a Saturday morning, which hosts 45 vendors selling Gulf Coast produce and handmade goods.

Water Valley

Water Valley thrived in 1848 as a railroad hub before facing years of decline after the Great Depression.

After its revival in 2010, the Main Street district became home to the Yalobusha Brewing Company (a 1890s foundry building) where you can try craft beers made from local grains.

The B.T.C. Old-Fashioned Grocery, inside the 1876 mercantile store, serves homemade lunches using recipes passed down through generations.

Add the restored 1937 Trusty Theater to your weekend plans for live music every Friday night.

Cleveland

Cleveland, originally a collection of cotton plantations, became a railroad town in 1869 and grew into a cultural center after Delta State University was founded in 1924.

The town played a key role in blues history, as many famous musicians performed at its juke joints along Highway 61. Today, the Grammy Museum Mississippi displays 4,000 music artifacts and interactive exhibits.

The newly expanded Cotton Row District features 28 locally owned shops in restored 1920s buildings. Walking tours of the historic downtown area, led by third-generation residents, cover 22 landmarks every Saturday.

Bay St. Louis

Bay St. Louis was founded as a French trading post in 1699 and grew into a resort town for wealthy New Orleans families in the 1800s.

While there, check out The Old Town district for the Second Saturday Art Walks. Smith & Lens Gallery highlights Gulf Coast photographers in a restored 1890s apothecary.

Ruth’s Roots community garden, created on a post-Katrina vacant lot, hosts weekly workshops on coastal gardening. The two-mile beachfront promenade, completed in 2024, includes historical markers that tell the town’s 300-year history.

New Albany

New Albany was founded in 1840 and became significant as William Faulkner’s birthplace. During the early 1900s, it was a cotton shipping point along the Tallahatchie River.

Downtown features 15 boutiques and antique shops in Victorian-era buildings, while the Union County Heritage Museum has expanded its Faulkner exhibit to include newly discovered family photographs and manuscripts.

Try the 44-mile Tanglefoot Trail during your weekend getaway, which follows the old GM&O Railroad route, drawing cyclists year-round.

Holly Springs

Holly Springs was once one of the wealthiest cities in the South before the Civil War. In 1862, General Ulysses S. Grant made the town his winter headquarters.

Today, 80 antebellum homes have been preserved, with 20 open for daily tours.

Phillips Grocery, operating since 1948 in a former saloon, serves locally sourced beef burgers using a 75-year-old recipe.

For a dash of history during your visit, drop by the Marshall County Historical Museum for its 3,000 Civil War artifacts, displayed in a restored 1850s law office.

Oxford

Oxford was chartered in 1837 as a center of learning and was chosen as the home of the University of Mississippi in 1848, earning its nickname, the “Cultural Mecca of the South.”

After surviving William Faulkner’s complex legacy and civil rights struggles, the town has now become a progressive college town.

The University of Mississippi Museum has also added 1,200 pieces of Southern folk art to its collection. Then there’s Square Books, located in three historic buildings on the courthouse square.

Canton

Canton was a major cotton market and railroad center before the Civil War and became Mississippi’s first film production center in 1996.

“A Time to Kill” was filmed on its historic square, and the Mississippi Film Studios have also hosted 25 major productions since 2020. The Canton Movie Museum also showcases props and costumes from local films.

Out here visiting? Get some smoked pork from Two Brothers Smoked Meats, an 1855 grocery store that uses hickory wood from local farms.

Check out the monthly flea market (pick up a quirky souvenir here), which has been attracting 200 vendors to the historic courthouse square since 1956.

Woodville

Woodville, founded in 1811, was once one of the wealthiest cotton-shipping points in antebellum Mississippi.

Rosemont Plantation, Jefferson Davis’s childhood home, also offers guided tours that highlight the complex history of the antebellum South.

The town’s African American Museum, housed in the 1876 Branch Bank building, documents the region’s civil rights struggles through oral histories and photographs.

Pass Christian

Pass Christian (affectionately known as the Pass) became a prestigious resort town along Mississippi’s Gulf Coast.

Today, the harbor supports 50 working shrimp and oyster boats, while the historic district preserves 120 pre-Civil War homes. For outdoor enthusiasts, The Oaks Golf Club offers a memorable experience with its par-72 layout.

To honor tradition, Pass Christian Art Association organizes plein air painting sessions along Beach Boulevard. It’s where artists capture the same coastal views that once attracted wealthy vacationers 150 years ago.

Laurel

Laurel, founded in 1882, was initially a lumber town that thrived during the timber boom of the early 1900s.

To illustrate this, the Lauren Rogers Museum of Art (Mississippi’s first art museum from 1923) displays collections that reflect the city’s wealth from the lumber industry.

Downtown Laurel features 40 locally owned shops and restaurants in restored brick buildings built between 1900 and 1930.

The Laurel Little Theatre, operating since 1927, produces 6 shows each year in a restored Arabian-style movie house. A must-do no matter which time of the year you visit this beautiful town.