Winter in the Mississippi Delta has a rhythm all its own. The days are cooler, the pace feels even more relaxed and there’s just something so inviting about settling into a warm restaurant, wandering through a museum or discovering a new corner of the Delta.
In Greenwood, winter is a season made for getting out. Spend a weekend enjoying the food, history, music and hospitality that make Greenwood special, then venture beyond to see where the Delta takes you.
Here, you’re encouraged to Stay & Stray: make Greenwood your home base, then use each day as an opportunity to explore more of the Mississippi Delta before returning for another memorable evening in town. With more than 300 locations included on our interactive map, there’s always another landmark, museum, restaurant, historic site or small town full of charm waiting down the road.
Pack a bag, clear your weekend and get ready to Find Your Beat from the Heart of the Delta.
Friday Evening: Make Yourself at Home in Greenwood
Your winter getaway begins in the heart of Greenwood.
Check into The Alluvian Hotel, where refined Southern hospitality and a downtown location make it an ideal home base for the weekend. For something a little different, settle into Tallahatchie Flats, a collection of restored sharecropper cottages along the Tallahatchie River that offers visitors a way to experience the real character of the Delta.
Once you’ve dropped off your bags, spend a little time getting acquainted with downtown. Browse the shelves at Turnrow Book Co., explore local shops along Howard Street or simply take in the historic architecture surrounding you. Greenwood’s downtown includes buildings dating from the late 1800s and early 1900s, giving even a casual walk a connection to the city’s past.
Then, warm up around the dinner table.
Reserve one of the private booths at Giardina’s, tucked inside The Alluvian, for seafood, steaks and Southern classics, or explore one of Greenwood’s many other locally loved restaurants. Food has long been one of the defining pieces of the Greenwood experience, and winter offers a particularly good excuse to settle in, order another course and make dinner the evening’s main event.
There’s no need to pack too much into your first night. You have an entire Delta weekend ahead of you!
Saturday Morning: Coffee, Shopping and a Little Greenwood History
Start Saturday with something warm.
Grab coffee and breakfast at Zoe Coffee Co. before spending the morning exploring downtown Greenwood. Pop into boutiques and galleries, search for something distinctly Mississippi to bring home or follow the historic streets to see another side of the city.
If you’re ready to dig deeper into the story of the region, make your way to the Museum of the Mississippi Delta. Its collections span centuries of Delta history and culture, with exhibits covering everything from prehistoric fossils and Native American artifacts to Civil War history and remnants of Choctaw Chief Greenwood Leflore’s home.
It’s a perfect place to begin a weekend in the Delta, giving you a more intimate appreciation for the region and its history. Before you start straying farther afield, you’ll have a better understanding of the land, people and history connecting the places you’re about to explore.
Saturday Afternoon: Stay Here. Stray There.
Now it’s time to stray!
Greenwood sits in the heart of a region filled with music history, cultural landmarks, small towns and stories that have influenced far more than the Mississippi Delta. The Stay & Strayexperience is about making Greenwood your home each night while giving yourself permission to follow whatever catches your interest during the day.
Use our Interactive Map to build your own route. You can filter more than 300 locations across the Delta by categories including museums, history, Civil Rights history, music history, shopping, dining, parks, entertainment and live music.
Music lovers might head toward Indianola to explore the legacy of B.B. King or travel north toward Clarksdale and the Delta Blues Museum. History enthusiasts can follow cultural landmarks and historic towns, while travelers looking for scenery can simply take the backroads and let the Delta landscape become part of the experience.
The best part? There’s no single route you have to follow!
Plan your Stay & Stray journey with our Interactive Map!
Choose a destination or two, leave a little room for an unexpected stop and see where the Delta takes you.
Saturday Evening: Come Back to Greenwood
After an afternoon on the road, point yourself back toward Greenwood and return to your home away from home.
Make Saturday night about good food and good company. Try Fan and Johnny’s for chef-driven Southern fare, head to Serio’s for an Italian steakhouse experience or see what else sounds good on Greenwood’s dining scene. If live music or a local event is happening during your stay, let the night go a little longer!
Or make relaxation the plan. Return to The Alluvian, grab a drink and enjoy the simple luxury of having nowhere else you need to be. After a day spent exploring the Delta, a comfortable room and an easy evening might be exactly what winter calls for.
Sunday Morning: One More Greenwood Experience
Before heading home, give Greenwood one more morning.
Enjoy a scrumptious breakfast and, if your schedule allows, make time for an experience you couldn’t fit into Saturday. Try something you haven’t done yet, ask the locals what they recommend or book some time at The Alluvian Spa for a relaxing end to your getaway.
Make Greenwood Your Winter Home Base
A winter weekend doesn’t have to mean staying inside until spring.
In Greenwood, cooler days offer another way to experience the Delta: lingering over a great meal, enjoying the crispness in the air and setting out along backroads that connect one Delta community to the next.
Stay in Greenwood. Stray across the Delta. Then come back and do it all over again.
Start planning with Visit Greenwood’s Stay & Stray itinerary, then use the Interactive Map to make the journey your own!
This winter, pack your bags, follow your curiosity and Find Your Beat from the Heart of the Delta.