Golf, Grub, & Good Vibes: A Guys’ Weekend in Tupelo

Whether it’s been months or years since your last trip together, Tupelo makes it easy to reconnect. From early morning tee times and afternoons spent savoring cigars to evenings filled with great food, live music, and easy conversation, Tupelo is positively the place for your next guys’ getaway.

Tupelo has plenty of solid places to stay, ideal for a laid-back guys’ weekend. Hotel Tupelo, located in the heart of downtown, combines style and comfort with subtle nods to Elvis’ roots and easy access to local restaurants, bars, and music spots. The Courtyard by Marriott offers easy access to retail, dining, and the Natchez Trace Parkway. Or, book a room at the Holiday Inn & Suites and enjoy spacious rooms and modern amenities in a convenient location. Wherever you land, you’re never far from good food, great music, and your next adventure.

Begin your getaway at Tupelo National Golf Club, where pine-lined fairways and well-kept greens offer a peaceful, challenging round for every skill level. It’s the kind of course where the pace is relaxed, the layout is thoughtful, and the only thing on your mind is the next shot. Or, if you'd rather keep things casual, tee off on a simulator at Backswings Golf & Grill, where you can grab a bite and enjoy the game at your own pace. Whether you’re in it for the friendly competition or just some time outdoors, it’s the perfect way to ease into the weekend.

Make your way to Neon Pig for a lunch that hits the spot. This local favorite serves up everything from a loaded shrimp po’boy and their signature smash burger to the chimmi steak sandwich. Don’t skip the housemade fries, the kind of side dish that steals the show.

Spring Street Cigars offers a well-curated walk-in humidor stocked with a wide range of premium cigars. Relax in the lounge with comfortable seating that encourages unhurried conversation and slow moments. Their knowledgeable staff is ready to help you find the perfect smoke to suit your taste.

As the sun goes down, head to Blue Canoe, a funky joint known for live music and seriously good food. Check out the menu beforehand and come hungry. You’ll want to try it all. From unique appetizers like Caribbean edamame or birria fries, to mouth-watering entrees like the Nashville-style hot fried soft shell crab sandwich, shrimp tacos, or grit-crusted catfish, you’re guaranteed to leave satisfied. Save room for the Connie’s Blueberry Donut Bread Pudding, a three-time winner of Mississippi Magazine’s Best Dessert in Mississippi award, made in collaboration with Connie’s Chicken, another Tupelo staple. It’s basically a Tupelo rite of passage, and once you try this delectable dish, you’ll understand why it’s earned a permanent spot on the menu.

The heart of the Blue Canoe experience is live music on the Cathead Stage, where talented local and touring artists perform nightly in a space that feels more like a backyard jam session. Over the years, the stage has hosted stars like Tyler Childers, Gary Clark Jr., and Alabama Shakes, all in the unassuming, music-loving space.

When you’re not quite ready to call it a night, step into Downunder. Ambient lighting, craft cocktails, and a speakeasy vibe make it the place to wrap up your night. Share a round of darts or a round of stories from the glory days, and keep the night going strong.

Ready to rally the crew? Kick off the next morning with brunch at Stables Downtown Grill. Located in Downtown Tupelo, this laid-back eatery, housed in a former livery stable, serves up a strong brunch game. Think hearty breakfast sandwiches, biscuits and gravy, and loaded omelets, or try the famous catfish nachos. If you’re simply looking for a caffeine fix, head to Strange Brew Coffeehouse, an inventive coffee shop in a revamped service station, offering everything from cold brews and pour-overs to creative signature drinks. Grab a seat, enjoy the brew, and ease into the day.

For a bit of fresh air, take a drive or a bike ride along the Natchez Trace Parkway, a scenic byway offering quiet views and open skies that turn a simple ride into something memorable. The nearby trails provide just the right balance of easy hiking and time to catch up. It’s a chance to step away from the usual pace and appreciate a slower rhythm with the guys.

No trip to Tupelo is complete without a visit to the Elvis Presley Birthplace and Museum, which offers an insightful look into the early life of the King of Rock ‘N’ Roll. The museum boasts memorabilia and stories that tell the story of his rise to fame, while the grounds provide a peaceful space to reflect on Elvis’ life as a young boy in Tupelo.

Your next guys’ getaway doesn’t have to be loud or over the top. In Tupelo, it’s about taking it easy, catching up, and enjoying the company of the guys who make the small moments enjoyable. From early tee times and late-night laughs to shared meals and easy conversations, this is the kind of trip that leaves you refreshed, not worn out. No pressure, no checklist, just time well spent. Imagine what you can do here!