8 Romantic Small Towns In Mississippi For A 3-Day Weekend
Any area known as the Magnolia State conveys a sense of romance, and these Mississippi towns fit the bill. From ornate homes in Natchez to a touch of fun in Tupelo, these destinations offer appealing options for a three-day weekend in Mississippi. Each town features Southern hospitality, historic inns within walking distance of romantic sites like The Square in Oxford, and access to natural beauty.
Biloxi is known for its casinos, but the city also offers options for a weekend for two, including the Biloxi Lighthouse and dolphin tours. Ocean Springs is an ideal destination for hand-in-hand strolls past historic homes and established art galleries, including the Walter Anderson Museum. Southern towns lend themselves well to romantic getaways, and these eight places stand out within the state.
Natchez
Historic Natchez is the oldest city in Mississippi, and its downtown reflects its age through well-restored buildings and a nostalgic atmosphere. Staying at the Monmouth Historic Inn and Gardens places guests in this historical setting. The antebellum home reflects the Southern character for which Mississippi is known and features an elegant garden, home tours, and refined dining options. It is just over a mile from Main Street, where walking maps of the district are available at Visit Natchez.
A stroll through town often begins at Bluff Park, a grassy promenade along Broadway that overlooks the Mississippi River and sets a relaxed pace. For couples interested in self-care, Natchez has several wellness centers, including Anruss and Company and Arabella Massage Therapy. The day can conclude at Guest House Mediterranean Restaurant, known for comfort food and Southern staples.
Biloxi
Biloxi is a popular destination for casinos, including the Hard Rock Hotel and Casino, which offers a romantic getaway with lively nightlife. There are also quieter ways to enjoy a three-day weekend, such as staying at classic inns like Rue Magnolia Bed and Breakfast or visiting the Biloxi Lighthouse. The 1920s inn is a renovated home that remains in the same family and provides a boutique coastal stay.
Sunset cruises and Deer Island ferry/boat rides with Biloxi Boat Tours offer views of the coastline and sunsets along the Gulf, especially after dinner at One Thirty One Lameuse. The restaurant is known for classic cuisine and regional seafood in the heart of the entertainment district. It also features an extensive wine list and a comfortable, intimate dining room suited to an evening out.
Ocean Springs
Ocean Springs blends creative energy with historic character, making its downtown district well suited to a romantic three-day weekend. The newly opened Beatnik features four floating cabins, a wet bar, and nature-inspired design elements for a calm, playful stay. The Roost is a classic boutique hotel surrounded by stately oak trees and within walking distance of historic landmarks. Together, these lodging options offer different perspectives on Ocean Springs while remaining close to one another.
The downtown area feels designed for leisurely walks. The Walter Anderson Museum of Art offers a quiet afternoon activity and celebrates the life of the artist through vibrant, regionally focused work. Dinner at Maison de Lu provides a comfortable setting for classic dishes with subtle Southern influences.
Bay St. Louis
Bay St. Louis offers sunset views, a coastal atmosphere, and a selection of intimate bed and breakfast inns. Visitors can stroll through local museums and galleries, including the Alice Moseley Folk Art Museum, before checking into the Pearl Hotel. It is a newer boutique property in downtown Bay St. Louis with a design that nods to the town’s coastal character.
The hotel includes the Thorny Oyster, a chef-driven dining venue specializing in coastal cuisine and a raw bar. The Pearl is also home to Hinge, a cocktail bar with a comfortable lounge setting. Craft cocktails and distinctive decor provide a relaxed way to end an evening in the downtown area.
Oxford
Oxford is home to the University of Mississippi, giving the historic district around Oxford Square an academic tone that complements its traditional architecture. The town also has a strong literary history and was home to authors John Grisham and William Faulkner. Rowan Oak, Faulkner’s former residence, is open for tours and adds context to a relaxed three-day weekend.
The Square, as locals call it, includes historic sites such as Neilson’s Department Store, the oldest in the South, along with restaurants like City Grocery, led by chef John Currence. Several historic hotels, including The Oliver and The Graduate, are located nearby and contribute to one of Mississippi’s most walkable downtown areas.
Mendenhall
Mendenhall has a quiet downtown centered on the Simpson County Courthouse, which reflects the town’s architectural character. For couples seeking privacy, the Johnny Knight Treehouse offers a distinctive place to stay. Set in a wooded area, the elevated bungalow-style lodge emphasizes seclusion, with the sound of a nearby creek and birds in the surrounding trees.
The town is known for its slower pace and hospitality, reflected in local spots such as Williams Cafe, which serves comfort food in a relaxed setting. A walk down Main Street leads to Alice E. Davis Memorial Park, offering a place to rest after dinner at Dinner On Main, a convenient option for those staying near the downtown area.
Tupelo
Tupelo is known as the birthplace of Elvis Presley, and walking tours of his childhood home add context and interest to a weekend visit. The downtown streets feature Elvis-related landmarks, including Tupelo Hardware Store, where his mother bought him his first guitar, and a larger-than-life statue in the center of town. The town also offers a range of lodging options suitable for extended stays.
Hotel Tupelo, located on Main Street, places visitors in the center of downtown and within walking distance of shops and restaurants. Its mid-century modern design complements the surrounding historic buildings. Nautical Whimsey Italian Bistro and Wine Bar reflects the town’s relaxed dining scene and is known for its al fresco seating and approachable menu.
Greenville
Greenville is rooted in Delta culture, with long-standing ties to American music and literature. It is also the birthplace of Jim Henson, creator of the Muppets, though he grew up in nearby Leland. The compact downtown area is well-suited to walking and includes dining options ranging from casual at Downtown Grille to fine dining at Louie’s Steakhouse. Historic hotels and bed and breakfasts contribute to the town’s appeal for a relaxed stay.
Hotel 27, formerly The Greenville Inn and Suites, was built in 1880 and is one of the town’s oldest buildings. The Belmont 1857 Bed and Breakfast is a restored antebellum mansion used for lodging and events. The Lofts at 517 offer modern accommodations with access to the Downtown Grille, providing a contemporary option within the downtown area.
A Weekend Pace Made for Two
From coastal retreats like Biloxi and Bay St. Louis to historic towns such as Natchez and Oxford, Mississippi offers a range of destinations well suited to a romantic three-day weekend. Walkable downtowns, historic inns, and locally owned restaurants create an easy rhythm that encourages slowing down and spending time together.
Whether the appeal lies in treehouse seclusion in Mendenhall, cultural landmarks in Greenville, or evenings spent wandering town squares and waterfronts, these towns share a sense of place that supports unhurried travel. Their scale and character make it possible to experience history, dining, and scenery without feeling rushed, which is often what defines a memorable weekend away in the Magnolia State.
