Stay and Stray
Greenwood is more than a destination — it’s the perfect home base for exploring the heart of the Mississippi Delta. With over 300+ places to discover, visitors can Stay and Stray each day, returning to Greenwood’s charming accommodations while venturing out to uncover the Delta’s rich culture, music, history and culinary treasures. Our interactive map makes it easy to plan your journey, from lodging and restaurants to museums, music landmarks, parks and entertainment. Whether you’re strolling historic streets, sampling world-class Delta cuisine, or taking a day trip to a nearby town, the map ensures every adventure connects seamlessly back to Greenwood, your nightly home base.
Day One: Arrival and Greenwood Immersion
Arrive in Greenwood and settle into the elegant Alluvian Hotel or the cozy riverside Tallahatchie Flats, your base for the journey ahead. Start your morning at Zoe Coffee Co., savoring artisanal coffee and fresh pastries that capture the warmth of local hospitality. Then explore downtown Greenwood, wandering past historic architecture and popping into galleries and boutiques, including the Delta Emporium, for one-of-a-kind finds. For lunch, enjoy the Italian-Southern fusion of Serio’s, where house-made pastas and locally sourced ingredients make each bite a celebration of the Delta. In the afternoon, join a hands-on session at Viking Cooking School, learning how regional ingredients transform into elevated dishes. End the day with a leisurely stroll along Grand Boulevard, admiring the tree-lined streets and enjoy a craft cocktail at your hotel as the evening settles over Greenwood.
Day Two: Delta Music and Culture
Fuel up with a wellness-inspired breakfast at Greenwood Nutrition before heading east to Clarksdale. Immerse yourself in the region’s musical heritage at the Delta Blues Museum, then step into Ground Zero Blues Club for a vibrant atmosphere steeped in history. Lunch at Abe’s Bar-B-Q delivers authentic Delta barbecue in a historic setting, pairing perfectly with the soulful surroundings. Spend the afternoon exploring Cat Head Delta Blues & Folk Art for local crafts and music memorabilia or browse the Senator’s Place gallery for contemporary culture. Wrap the day back in Greenwood with dinner at Giardina’s, where seasonal ingredients and refined Southern techniques highlight the depth of Delta cuisine. End the evening with live blues or jazz in town, keeping the music alive as you rest for tomorrow’s adventure.
Day Three: Heritage Trails and Scenic Escapes
Begin your day with breakfast at By the Bridge Bistro, enjoying fresh, elevated fare that sets the tone for exploration. Venture out to Indianola and visit the B.B. King Museum to experience the life and legacy of the blues legend. Stop for lunch at The Blue Biscuit, savoring slow-smoked meats in a vibrant, music-filled atmosphere. In the afternoon, wander the historic town of Friars Point or take in natural beauty at Yazoo Pass, a serene Delta waterway perfect for reflection and photos. Return to Greenwood for dinner at Fan & Johnny’s, sampling comfort food with a modern twist and spend the evening strolling the city streets or relaxing at your lodging.
Day Four: Museums, Nature and Culinary Surprises
Enjoy breakfast at Veronica’s Custom Bakery then explore the Museum of Mississippi Delta to learn about agriculture, history and art unique to the region. Take a stroll through downtown Greenville, taking in murals and local shops, or stop at the Winterville Mounds to experience ancient Native American history. Lunch at Doe’s Eat Place offers legendary steak in a historic, James Beard-recognized setting, giving a taste of true Delta culinary tradition. In the afternoon, connect with nature at Leroy Percy State Park or the Theodore Roosevelt National Wildlife Refuge, experiencing the region’s rivers, trails, and wildlife. Return to Greenwood and have dinner at What’s Cooking, enjoying a relaxed evening with flavors that showcase the Delta’s richness.
Day Five: Final Strays and Farewell Flavor
Start your last day in Greenwood with breakfast at a local favorite café, then venture out on a final stray. Visit Dockery Farms near Cleveland, known as the birthplace of the blues, or stop at Mont Helena for a historic plantation tour. For lunch, indulge in classic smoked meats at Drake’s BBQ back in Greenwood before a final stroll along Grand Boulevard to soak in the city’s architecture and charm. In the afternoon, if time allows, visit the Back in the Day Museum for a last dose of Delta history. Depart with a full sense of the Delta’s flavor, music, culture, and hospitality, having experienced a rich and unforgettable journey with Greenwood as your nightly home base.
Your five-day Stay and Stray adventure leave you with a deep sense of the Mississippi Delta’s flavor, history and culture. With over 300+ authentic experiences to explore, the interactive map continues to guide you beyond this itinerary, helping you uncover new culinary hotspots, music venues, museums and scenic escapes. Greenwood remains your welcoming home each evening, offering comfort, charm and easy access to the Delta’s endless discoveries. Every Stay and Stray moment tells a story, inviting you to return again to experience the true spirit of the Delta.