Three ways to spend a summer weekend in one of Mississippi’s most versatile towns.
Tupelo is the kind of place that can shapeshift depending on who you bring with you. It can be a slow girls’ weekend full of rooftop dinners and mead tastings. A family trip built around buffalo feedings and Elvis history. Or an outdoorsy escape where the days are spent paddling, hiking, and finding the next trailhead. That’s part of the charm. You can come back more than once and do it differently every time.
For the Girls
Friday
Check into Hotel Tupelo and settle into downtown. Start with cocktails and small plates at Jobos before wandering Main Street, popping into boutiques and local shops, and ending the night at Park Heights for rooftop views and dinner.
Saturday
Ease into the morning with coffee at Lost + Found Coffee Company or Strange Brew, then browse the Tupelo Farmers Market at The Depot. Spend the afternoon shopping across Downtown, Midtown, and Barnes Crossing. Break for a mead tasting at Queen’s Reward Meadery, Mississippi’s first and only meadery.
For dinner, grab a table at Nautical Whimsey for handmade pasta or Loco Taco for margaritas and tacos. If you’ve still got energy, head to Romie’s Grocery for patio music and one more round.
Sunday
Start with bagel bombs and coffee at Mae’s To-Go Cup, then book a facial or massage at Creative Touch Day Spa or Pilates at Haven Studio. Before heading home, squeeze in one last walk on the Natchez Trace Parkway.
For the Family
Friday
Start strong at Connie’s Chicken. Order the chicken biscuits and don’t leave without trying the blueberry donuts.
Spend the afternoon at the Tupelo Buffalo Park & Zoo, where giraffes, zebras, and buffalo keep kids entertained for hours. End the day with burgers, fries, and milkshakes at Johnnie’s Drive-In, where Elvis once had his regular order.
Saturday
Fuel up at Brick & Spoon or Kreecher’s Creations, then head to the Elvis Presley Birthplace and Museum. Walk through the tiny two-room house and let the kids imagine how the King got his start.
After lunch at Amsterdam Deli & Grill, spend the afternoon exploring the Civil Rights & African American Heritage Trail or cooling off at Veterans Memorial Park’s splash pad.
Dinner at Jobos keeps things easy, followed by dessert downtown. Pick between Funky Cones, Scoops & Brews, or Crave.
Sunday
Take a scenic drive on the Natchez Trace Parkway and stop for a picnic or short hike before heading home.
For the Outdoorsy Crowd
Friday
Check into town and get your gear together. Stop by Trails & Treads or Core Cycle + Outdoor if you need anything for the weekend.
Dinner at Blue Canoe means you can enjoy live music while you eat before an early night.
Saturday
Start at Connie’s Chicken, then head out to Tombigbee State Park. Spend the day kayaking, paddleboarding, fishing, or hiking the trails.
Back in town, take the Elvis’ Tupelo Self-Guided Bicycle Tour and explore Tupelo’s mural and heritage trails.
Dinner at Amsterdam Deli & Grill means authentic Mediterranean food with an Italian twist, a perfect end to a day exploring.
Sunday
Get in one last hike on the Natchez Trace Parkway before grabbing pastries and coffee at Strange Brew for the road.
No matter which version of Tupelo you choose, the city makes it easy to settle in. Stay for the music, the food, the trails, or the stories. Then come back and try it another way.
