Once a prominent port and the capital of Mississippi, and still the southern terminus of the Natchez Trace, Natchez’s glory days seem to be a good century behind it. The oldest settlement on the Mississippi River, founded as Fort Rosalie in 1716 by French colonialists two years before New Orleans, Natchez prospered for quite some time until railroads replaced steamboats and local industries closed. Now only the 25^th largest city in the state, it could easily fall off the radar, but that would be a shame, because I found Natchez to be irrefragably one of the most atmospheric cities in the United States. Its shrinking size is handily counterbalanced by the city’s ability to combine its deep history (make sure to visit the First Presbyterian Church to view a fantastic collection of black-and-white photos of everything from 1800s society ladies in flamboyant hats to a river baptism) with a contemporary vibe (pop into the trendy Natchez Coffee Company for a Belgian chocolate shake), and, of course, the plenitude of its glorious buildings. These are my favorites.

#1 Longwood Plantation

This oddball home—the largest octagonal house in the United States—was the brainchild of a Philadelphia architect who came up with a design for an “Oriental villa” for his clients, wealthy cotton planter Haller Nutt and his wife, Julia. Construction of Longwood Plantation began in 1860, with a modified plan that de-emphasized the Asian aspect, and continued until the start of the Civil War, when the northern workers employed there literally dropped their tools and left. Work progressed more slowly now, and the exterior (including a red-topped dome and genteel columned porches) and basement level were completed, but Nutt died in 1864 and the rest of the home was never finished. Julia and their eight children lived in the (very comfortable) basement level until she died in 1897. Today, “Nutt’s Folly” is open to the public via small tours, which I promptly joined after moseying around the grounds that used to be orchards and rose gardens. The interconnected rooms of the basement epitomize the gentility and refinement of the well-to-do-family, but the unfinished upper stories, with bare brick walls and the intricate wood construction of the dome, left me wondering what might have been.

#2 Dunleith Plantation

I was neither a guest of the inn nor of the wedding that was about to start, but I managed to talk my way onto the grounds of the grand Dunleith Plantation with a promise not to disturb the ceremony. Although a happy event was about to unfurl, this iconic plantation house comes with its fair share of tragedy. The original house burned to the ground after the owners’ daughter, who was already a widow at age 15, inherited it. Her second husband had this new house built, in 1856, but she died three years later, and he sold it off to settle the estate. Now a luxury inn, Dunleith was built in the Greek Revival style on a 40-acre estate and declared a National Historic Landmark in 1974. Porches and 26 brick-and-stucco Tuscan columns encircle the entire building on the first and second floors, and chimneys and steep dormer windows puncture the roofline. Although I couldn’t finagle my way inside, what with the bride and groom about to make their appearance on the flower petal–strewn lawn and the musicians on the porch starting to cue them with their violins, the exterior of Dunleith alone impressed me in a very big way.

#3 Magnolia Hall

Built in 1858, Magnolia Hall was the last mansion to be constructed in downtown Natchez before the Civil War. One of the most impressive of the properties that compose the Natchez On-Top-of-the-Hill Historic District, this Greek Revival mansion features four soaring Ionic columns supporting an unadorned portico. A short staircase leads up to the main entrance and the ground-floor porch, with tall shuttered windows on either side of the elegant doorway. A second-story porch certainly would have been a favorite spot to relax for the original owner, a wealthy merchant, planter, and cotton broker. Situated on a generous corner lot, it’s easy to see the building in its entirety, with a rear that echoes the front. If you’re inclined to go inside for the tour, you’ll find rooms filled with antiques from the mid-1800s and a costume collection upstairs.

#4 St. Mary Basilica

Another contributing property to the Natchez On-Top-of-the-Hill Historic District, this brick Gothic Revival structure is the city’s most beautiful house of worship. Completed in 1886 as the only building in Mississippi constructed as a cathedral (it was promoted to basilica in 1998), St. Mary remains the oldest Catholic building still in use in the state. Designed by a local architect, the basilica features lovely ornamental pinnacles, a recessed Gothic-arched entrance, and a central tower, topped with a spire and sporting clocks with different faces, that houses the “Maria Alexandrina,” a 3,000-lb. bell with reliefs of the Blessed Virgin and of garlands held by cherubs, a gift from the Italian Prince Alessandro Torlonia. Inside, I was attracted by the deep blue groin vault ceiling, supported by slender compound columns; the semicircular apse; the numerous statues on corbel shelves and in niches; the finely carved pews; and the particularly lonesome Crucifixion scene within an ogee arch above the Carrara marble reredos on the altar. Sixteen gorgeous stained-glass windows, 12 of which were made in Austria, honor the likes of St. Stephen, St. Lucy, and St. Catherine of Siena.

#5 Rosalie Mansion

Framed by front and rear porches and two-story columns, this brick Greek Revival building with black shutters and expansive lawns and gardens is not only one of the most handsome edifices in Natchez, it also boasts a proud and memorable history that starts way back in 1820, when one Peter Little purchased the land that is the site of Rosalie Mansion today. He married the daughter of his friends after the husband died of yellow fever and the wife was nearing death from the same disease, but it wasn’t exactly legal yet: Eliza was only 14. He sent her off to school in Baltimore, and their long-distance love affair thrived. When she returned, they moved into Rosalie, completed in 1823 and retaining the name originally given to the fort built by the French. The couple remained happily married, though childless, for 45 years. But children found their way into Rosalie when Eliza helped found the Natchez Children’s Home. Eventually, Eliza died, and Peter followed three years later—without a will. Rosalie 2.0 began when another childless couple acquired the mansion and also took orphans into their home, adopting one girl as their own. That girl would go on to marry and raise six children at Rosalie, despite the Yankee snag it hit when General Grant took possession of the mansion to use as Union Army headquarters in 1863. Two of those children eventually sold Rosalie in 1938 to the Daughters of the American Revolution, with the stipulation that they could live there, while giving daily tours. In 1958, the last daughter died, ending the family’s occupation for good.

Five Runners-up

• Stanton Hall (1857)
• Temple B’nai Israel (1905)
• First Presbyterian Church (1830)
• Prentiss Club (1905)
• Choctaw Hall (1836)