The Natchez Trace Parkway Road Trip Itinerary: Natchez - Ridgeland - Tupelo
Darley Newman at golden hour along the Mississippi River in Natchez, with the bridge stretching across the horizon above Under-the-Hill.
Darley Newman at Natchez’s historic Under-the-Hill Saloon, raising a pint and riding the legendary carved elephant—something you have to do when you’re here.
Day 2 – Natchez: Stories That Shaped a Nation
Longwood 140 Lower Woodville Road, Natchez, MS 39120
America’s largest octagonal home, famously unfinished when the Civil War began. Known as “Nutt’s Folly,” this hauntingly beautiful mansion tells a story of ambition interrupted.
Local insight often shared by historian Dana-Marie Geoffrian.
Dr. John Bowman Banks Museum 9 St. Catherine Street, Natchez, MS 39120
Home of Natchez’s first Black physician and a Civil Rights organizing hub in the 1960s. Powerful stories of resilience are preserved here.
Historical context frequently shared by Dr. Roscoe Barnes III and Thelma Newsome.
Downtown Natchez (Main, Commerce & Franklin Streets)
Boutique shopping, galleries, and bakeries such as Butter Cakery, Darby’s, Natchez Olive Market, and Dixon Books. Southern hospitality meets creative spirit.
Open Air Tours with Guide Sal Durkin Departs from 200 North Broadway Street (Visit Natchez Depot)
Local guide Sal Durkin brings Natchez alive with colorful storytelling and insider stops you might otherwise miss.
Natchez City Cemetery 2 Cemetery Road, Natchez, MS 39120
A blufftop resting place overlooking the Mississippi River. Legends like “Louise the Unfortunate” and the mysterious “Turning Angel” monument make this both peaceful and fascinating.
Drive: Natchez → Ridgeland
Drive the Natchez Trace Parkway North
Scenic overlooks, forested trails, and historic markers line this 444-mile route tracing ancient Native American travel corridors.
Distance: ~140 miles
Time: ~2 hours 30 minutes
Route: US-84 East to I-55 North or scenic segments of the Natchez Trace Parkway
This stretch transitions from Mississippi River bluffs to rolling hills and pine forests.
Darley Newman welcoming sunset at the Reservoir Overlook in Ridgeland along the Natchez Trace—an inviting picnic, soft skies, and Mississippi beauty stretching to the horizon.
Day 4 – Ridgeland: Artisans & the Old Trace
Specialty Shopping & Wellness
(Unique Finds & Holistic Living)
Railroad District Shopping Jackson Street Area, Ridgeland, MS 39157
A walkable collection of locally owned boutiques and specialty shops blending small-town charm with curated style.
Fischer Galleries 1000 Highland Colony Parkway, Suite 6002, Ridgeland, MS 39157
A premier Southern gallery showcasing masterworks, including portraits of William Faulkner and Eudora Welty.
Director: Marcy Fischer Nessel.
Lily Pad Café 115 W. Jackson Street, Ridgeland, MS 39157
A charming community-focused café and arts hub offering fresh, seasonal fare in an inviting creative space. It’s a relaxing stop that blends culture, conversation, and comfort food.
CW Organics Apothicaire & Tea Room 103 West Washington St, Suite B4
Ridgeland, MS 39157
An elegant herbal apothecary offering organic teas and a Traditional Tea Service experience. Step inside for a calming retreat rooted in holistic wellness.
Owner: Caroline Warner.
Renaissance at Colony Park 1000 Highland Colony Parkway, Ridgeland, MS 39157
Upscale open-air shopping anchored by beautiful fountains at either end — ideal for a relaxed afternoon stroll.
The Township at Colony Park Highland Colony Parkway, Ridgeland, MS 39157
A modern lifestyle district focused on wellness, dining, and elevated retail experiences.
J. Olive 1000 Highland Colony Parkway, Suite 5002, Ridgeland, MS 39157
Sample fresh olive oils and aged balsamic vinegars sourced from both hemispheres for peak freshness. Learn about the artisanal production process while tasting global flavors.
Mississippi Crafts Center 950 Rice Road, Ridgeland, MS 39157
Watch artisans create pottery, woodwork, Choctaw baskets, and quilts. A living tribute to Mississippi craftsmanship.
Craft demonstrations often led by artisans like Brian Hill and Diane Williams.
Natchez Trace Parkway – Old Trace Boardwalk Near 950 Rice Road, Ridgeland, MS 39157
A peaceful walk-through ancient pathways once traveled by Native Americans and early settlers.
Cypress Swamp (Milepost 122, Natchez Trace Parkway)
A hauntingly beautiful boardwalk over still waters filled with cypress knees — a photographer’s dream.
Old Trace Boardwalk located in the grounds of the Mississippi Crafts Center - a great place to quiet down and reflect.
Where to Stay in Tupelo
(Rock ’n’ Roll Roots, Native Heritage & Down-Home Flavor)
Hotel Tupelo, a Wyndham Hotel 314 East Main Street, Tupelo, MS 38804
A stylish downtown boutique hotel within walking distance of restaurants and music landmarks.
Day 5 (contd.) - Tupelo
Culinary Experiences & Local Dining
(Tasting Tupelo: Flavorful Bites & Local Favorites)
Forklift Restaurant 1103 West Jackson Street, Tupelo, MS 38804
A local favorite for inventive Southern cuisine and craft cocktails served in a stylish, laid-back setting. Expect beautifully plated dishes and a lively evening atmosphere.
Blue Canoe 2006 North Gloster Street, Tupelo, MS 38804
Part restaurant, part music venue, this eclectic Tupelo staple serves bold Southern flavors alongside live local performances — colorful, energetic, and uniquely Mississippi.
Mae’s To Go Cup 335 East Main Street, Tupelo, MS 38804
A cozy coffee stop filled with Elvis-inspired artwork and small-town charm. Grab a latte and pastry before exploring downtown.
King Chicken Fillin’ Station 107 Stone Street, Tupelo, MS 38804
A retro gas station turned beloved chicken spot — casual, nostalgic, and packed with flavor.
Johnnie’s Drive-In 908 West Main Street, Tupelo, MS 38804
Order the famous doughburger, fries, and milkshake — and sit in the Elvis Booth for a true rock ’n’ roll moment.
Queen’s Reward Meadery 137 Courthouse Square, Tupelo, MS 38804
Mississippi’s first female-owned meadery crafting small-batch honey wines from 100% local honey.
Owner: Jeri Carter.
Darley Newman savoring a legendary Doughburger at Johnnie’s Drive-In in Tupelo—beneath the watchful gaze of Elvis, right at the spot where he once sat.
Closing Moments
End your journey reflecting on the Mississippi River in Natchez or beneath towering trees along the Trace. This road trip blends soulful flavors, Civil Rights history, artisan traditions, Native heritage, and the birthplace of rock ’n’ roll — all connected by one of America’s most scenic highways.
A journey through river towns, soulful cuisine, Civil Rights history, artisan craftsmanship, and Elvis’s roots.
Total Route Distance: ~320 scenic miles along and near the Natchez Trace Parkway
Where to Stay in Natchez
(Historic River Town Charm & Deep Southern Flavor)
Natchez Grand Hotel & Suites 111 S. Broadway Street, Natchez, MS 39120
Overlooking the Mississippi River bluff, this centrally located hotel offers modern comfort just steps from downtown dining, shopping, and sunset views. Request a river-view room for a front-row seat to unforgettable golden-hour skies.
Day 1 – Natchez: River Views & Southern Flavor
Fat Mama’s Tamales 303 S. Canal Street, Natchez, MS 39120
A Natchez institution famous for Delta-style tamales, “Fire & Ice” pickles, and its legendary “Knock-You-Naked” margarita. Expect colorful charm and stories from owner James Gammill III.
Under-the-Hill Saloon 25 Silver Street, Natchez, MS 39120 (Under-the-Hill District)
One of the oldest bars on the Mississippi River, where riverboat gamblers and outlaws once gathered. Come at sunset for sweeping river views and a sense of Old West mystique.
Natchez Coffee Company 509 Franklin Street, Natchez, MS 39120
A cozy downtown café perfect for recharging before an afternoon stroll through historic streets lined with 19th-century architecture.
The Donut Shop 501 John R. Junkin Drive, Natchez, MS 39120
A classic Southern morning stop — simple, sweet, and beloved by locals.
Darley Newman with owner, David Gammill at Fat Mama’s Tamales, digging into tamales and sipping the restaurant’s famously strong Knock-You-Naked Margaritas.
Darley Newman with her guide, Dona-Marie Geoffrion outside iconic Longwood Mansion in Natchez, Mississippi, the largest octagonal house in the U.S. and a true Southern landmark.
Where to Stay in Ridgeland
(Scenic Trails, Culinary Gems & Mississippi Craftsmanship)
The AC Hotel by Marriott Jackson Ridgeland 221 Township Avenue, Ridgeland, MS 39157
Modern European-inspired design in the Township at Colony Park — walkable to dining and shopping.
Day 3 – Ridgeland: Nature, Biking & Elevated Southern Dining
Explore Ridgeland Visitor Center 1000 Highland Colony Parkway, Ridgeland, MS 39157
Your gateway to the city’s biking culture and outdoor adventures. Grab a bikeshare and hit the trails.
Whirl Smoothie Bar 108 North Railroad Avenue, Ridgeland, MS 39157
A health-forward café in the Railroad District — think açaí bowls, smoothies, and strong coffee.
Chisha Foka Multi-Use Trail Accessible near Jackson Street, Ridgeland, MS 39157
A peaceful green corridor popular with cyclists and joggers, connecting nature to the charming Railroad District.
Reservoir Overlook – Barnett Reservoir Near 1000 Highland Colony Parkway, Ridgeland, MS 39157
Sunset over shimmering waters makes this a birdwatcher’s paradise. Perfect for a scenic picnic.
Shapley’s Restaurant 868 Centre Street, Ridgeland, MS 39157
An elegant Southern surf-and-turf staple for over 40 years. Known for steaks, seafood, and an exceptional wine list.
Family-owned by Mark Shapley.
Darley Newman with Marcy Fischer Nessel at Fischer Galleries, standing beside portraits of Eudora Welty and William Faulkner by artist Rosie Ferguson Gathings.
Darley Newman with owner, Caroline Warner at CW Organics Apothicaire & Tea Room—sharing tea, treats, and a cozy moment in one of Ridgeland’s most charming spots.
Continue North to Tupelo
Drive: Ridgeland → Tupelo
Distance: ~180 miles
Time: ~3 hours
Route: Primarily along the Natchez Trace Parkway
This is one of the most beautiful stretches of the Parkway — gentle curves, wildlife sightings, historic pull-offs, and quiet forest scenery.
Day 5 – Tupelo: Elvis & Local Legends
Historic & Cultural Landmarks
(Exploring Tupelo’s Legacy: Elvis and Beyond)
Elvis Presley Birthplace & Museum 306 Elvis Presley Drive, Tupelo, MS 38801
Step inside the humble two-room home where Elvis was born and explore the museum chronicling his rise from Tupelo to global stardom. The peaceful chapel and grounds add a reflective touch to this iconic stop. Stop at the Mural art by Betty Harper.
Fairpark 400 North Spring Street, Tupelo, MS 38804
A beautifully maintained downtown park featuring the striking Elvis Homecoming statue and the Chief Piominko statue honoring Chickasaw heritage. It’s a meaningful intersection of music history and Native American legacy.
Tupelo Hardware Company 114 West Main Street, Tupelo, MS 38804
The legendary store where Elvis purchased his first guitar — a small shop that helped spark a musical revolution. The store is currently closed but the public can peak through the windows and take a selfie outside this historic location.
Relics Antique Marketplace 1906 North Gloster Street, Tupelo, MS 38804
Housed in the former garment factory where Elvis’s mother, Gladys Presley, once worked while pregnant with him. Today it’s an expansive antique marketplace layered with local history and vintage treasures.
Milam Elementary School 1000 West Main Street, Tupelo, MS 38804
The school Elvis attended for 7th and 8th grade — a modest but meaningful landmark marking his early formative years in Tupelo.
Darley Newman with Roy Turner at the Elvis Presley Birthplace in Tupelo, as Roy shares stories from Elvis’s childhood where it all began.
Day 6 – Tupelo: Native Heritage & Scenic Overlooks
Chickasaw Village Site (Milepost 261.8, Natchez Trace Parkway)**
A reconstructed Chickasaw settlement offering insight into the region’s earliest inhabitants.
Director: Brady Davis.
Old Town Overlook (Milepost 263.9)**
Sweeping views of Tupelo’s landscape — especially stunning at golden hour.
Natchez Trace Parkway Visitor Center 2680 Natchez Trace Parkway, Tupelo, MS 38804
An informative stop to deepen your understanding of the Trace’s 10,000-year history.
Darley Newman with Brady Davis at the Chickasaw Village Site along the Natchez Trace—sharing the history, culture, and the living stories of the land.
