10 Mississippi Small-Town Getaways That Are Perfect For A November Weekend Escape
Last November, I ditched my usual couch marathon for a road trip through Mississippi, and it turned out to be the best impulse decision I’ve made in years.
Small towns across the Magnolia State wake up in autumn with festivals, clear skies, and Southern charm. One minute you’re chasing live blues under string lights; the next you’re touring columned mansions, sipping sweet tea on porches, or wandering quiet streets where nobody knows your name.
Leafy byways, farm stands, and smoky barbecue connect the dots. If November’s calling, answer it—Mississippi’s hidden gems are ready to turn a weekend into a memory.
1. Ocean Springs
Picture this: a Gulf Coast town where every corner feels like an art gallery came to life and decided to throw a party. Ocean Springs wraps you in creativity the moment you arrive, with murals splashed across brick walls and studios tucked between oak trees dripping Spanish moss.
Mark your calendar for the Peter Anderson Arts & Crafts Festival on November 8–9, 2025, when over 400 artists transform downtown into an open-air wonderland. You’ll find everything from pottery to paintings, plus food vendors who understand that art appreciation requires serious snacking.
Between festival stops, wander the walkable streets lined with quirky boutiques and waterfront views that make you forget what day it is.
2. Natchez
Natchez perches on bluffs above the Mississippi River like it’s still waiting for steamboats to round the bend. Grand antebellum homes line the streets, each one holding stories that’ll make your history teacher weep with joy.
But here’s where it gets deliciously spooky: the Angels on the Bluff cemetery tours run November 6–8, 2025, guiding you through Natchez City Cemetery after dark. Costumed storytellers bring historic residents back to life (figuratively, thankfully), sharing tales of river barons, Civil War drama, and characters who shaped the South.
When daylight returns, explore mansion museums and riverfront parks where the views stretch for miles across the mighty Mississippi.
3. Bay St. Louis
Bay St. Louis rebuilt itself after Hurricane Katrina with an artist’s eye and a rebel’s heart. Old Town now bursts with galleries, studios, and restaurants where chefs experiment like they’ve got nothing to lose and everything to prove.
The monthly Second Saturday Art Walk on November 8, 2025, turns the entire downtown into one big creative block party. Gallery doors swing open, artists chat about their process, and live music spills onto sidewalks where you can sip coffee and pretend you’re sophisticated.
Between art stops, the beach beckons just blocks away, offering sunset views that remind you why people write songs about the Gulf Coast.
4. Laurel
Thanks to HGTV’s Home Town, Laurel transformed from a sleepy lumber town into a destination where people actually plan vacations around seeing freshly renovated historic homes. Downtown explodes with murals that turn ordinary walls into Instagram gold, each one celebrating local history or just being ridiculously photogenic.
Wing Wars hits town on November 8, 2025, because nothing says sophisticated getaway like a chicken wing competition that takes itself very seriously. Local restaurants battle for bragging rights while you happily judge every crispy, saucy entry.
Beyond the fried food glory, boutiques and coffee shops fill restored buildings where you can browse vintage finds and wonder why your hometown doesn’t look this good.
5. Oxford
Oxford wraps itself around a square that feels lifted from a novel, probably because so many writers have haunted its bookstores and cafes over the decades. William Faulkner’s Rowan Oak estate sits just beyond downtown, where you can wander rooms frozen in literary history and imagine typing masterpieces on ancient typewriters.
November brings concerts, holiday kickoff events, and that perfect college-town energy where coffee shops stay packed and conversations run deep. Square Books anchors the downtown, stacking shelves floor to ceiling with Southern literature and random treasures you didn’t know you needed.
Between cultural stops, grab a table at any square-side restaurant and watch the world pass by at that slow Mississippi pace.
6. Clarksdale
Clarksdale doesn’t just claim blues heritage; it breathes it through every juke joint, street corner, and worn guitar case leaning against bar stools. Live music fills the air 365 nights a year, and November’s lineup packs venues with legends and newcomers who all understand that the Delta invented something magical here.
Ground Zero Blues Club, Red’s Lounge, and Cat Head Delta Blues & Folk Art create a circuit where you can hop from one authentic experience to another. The Delta Blues Museum anchors downtown, displaying instruments and stories that trace how sharecroppers’ songs became America’s soundtrack.
Between sets, explore crossroads where Robert Johnson supposedly made his famous deal, because even the streets here have backstories.
7. Cleveland
Cleveland punches way above its weight class thanks to the GRAMMY Museum Mississippi, a gleaming tribute to American music that somehow landed in the heart of Delta cotton country. Open Tuesday through Sunday, the museum traces everything from gospel to hip-hop, with interactive exhibits that let you mix tracks and pretend you’re the next big producer.
Downtown events pepper the fall calendar, turning the compact historic district into a gathering spot where locals and visitors mingle over live performances and seasonal markets. Delta State University adds youthful energy to streets lined with mom-and-pop shops that have survived decades of economic shifts.
The whole town feels like a love letter to resilience and rhythm.
8. Greenwood
Greenwood’s Alluvian Hotel & Spa rises from the Delta like someone decided this cotton town deserved five-star treatment and marble everything. Rooms feel lifted from a magazine spread, complete with spa services that erase every road-trip kink from your shoulders.
But don’t hole up in luxury all weekend—the walkable historic core demands exploration. Viking Range Corporation was born here, so cooking stores and culinary events celebrate the town’s unexpected foodie credentials. November brings farmers markets, live music on the square, and that Delta hospitality where strangers greet you like long-lost cousins.
Turnrow Book Co. stocks shelves with Southern literature perfect for post-spa reading sessions on your private balcony.
9. Corinth
Corinth sits where two railroad lines crossed during the Civil War, making it a battlefield prize that changed hands and changed history. Today, small museums and preserved sites let you trace troop movements without dodging actual cannon fire, which honestly improves the whole experience.
The SoCo (South Corinth) shopping district breathes new life into historic buildings, filling them with boutiques, antique shops, and cafes where you can refuel between history lessons. Downtown stays compact enough to explore on foot, which means you can park once and forget your car exists for an entire afternoon.
November’s mild weather makes wandering these streets absolutely perfect for soaking up stories without sweating through your shirt.
10. Tishomingo / Iuka
Tishomingo State Park breaks every flat Mississippi stereotype with rocky outcrops, fern-covered trails, and terrain that looks lifted from Appalachia and dropped into the northeast corner of the state. November cools the air to perfect hiking temperature, when you can climb without feeling like a melting popsicle.
National Take a Hike Day on November 17, 2025, brings organized trail events and ranger-led walks through the park’s most scenic spots. Bear Creek winds through the property, offering swimming holes that brave souls still enjoy in early November before winter truly arrives.
Nearby Iuka adds small-town charm with diners and shops for post-hike recovery meals that taste better when you’ve earned them.