Holiday Magic in Tupelo: Your Ultimate Guide to Shopping, Dining, and Celebrating the Season

Revel in the magic of the holidays with the Downtown Tupelo Holiday Open House, November 9 from 1-5 p.m. Spend the afternoon strolling through beautifully decorated streets, shop exclusive holiday deals from local merchants, and enjoy a bite to eat at your favorite downtown restaurants. Don’t forget to snap a photo with Santa Claus, who will spread plenty of joy with special appearances throughout the day. Gather your family and friends, soak in the festive atmosphere, and celebrate the spirit of the season while supporting the small businesses that make Downtown Tupelo shine.

Tupelo is home to three distinct shopping districts: Downtown, Midtown, and Barnes Crossing, each filled with its own distinctive holiday flare. In Downtown Tupelo, historic streets glow with twinkling lights and cheerful window displays, inviting you to explore locally owned boutiques like L.A. Green, Spring, and Fleet Feet, alongside Reed’s, a 120-year-old department store, offering clothing and accessories for men, women, and children, as well as a curated gift shop and independent book store. Midtown is a treasure trove of artisan goods and hidden gems, featuring favorites like Elizabeth Clair’s and Jody’s, perfect for those seeking truly one-of-a-kind gifts. Meanwhile, Barnes Crossing offers the convenience of national retailers and big-brand favorites. Whether you’re searching for handcrafted keepsakes or popular must-haves, Tupelo has the perfect gift waiting for everyone on your holiday list.

Downtown Tupelo will transform into a winter wonderland for Deck The Depot, a festive market experience at The Depot, November 22. Stroll through a cozy marketplace filled with artisan vendors, Downtown merchant pop-ups, and delicious seasonal treats from favorite Tupelo Farmers Market bakers and local food trucks. Enjoy the sights and sounds of the season with live holiday performances, Christmas photo ops, and fun crafts and activities for the kids. With sparkling lights, joyful music, and plenty of cheer, Deck The Depot is the perfect place to shop, savor, and celebrate the spirit of the holidays, Downtown Tupelo style.

Mornings are made a little more magical with a holiday-inspired cup of coffee, like the gingerbread latte paired with a fresh blueberry Danish from Strange Brew Coffeehouse. For lunch, savor the warm hospitality and delicious Southern flavors at Sweet Tea & Biscuits, featuring daily specials and favorites like the Fried Green Tomato BLT, Momma’s Famous Chicken Salad, and the Trio Salad Plate. After your meal, make the most of your time in Tupelo by checking off your holiday shopping list at the adjoining boutique, The Vine Collection.

Warm up and celebrate the season at Nautical Whimsey with cozy Italian flavors, featuring dishes like rosemary focaccia bread, Florentine stuffed ravioli, prosciutto scampi, chicken parmesan, and more. Pair your meal with their Italian Christmas Spritz, a sparkling, citrusy delight featured on the Tupelo Holiday Cocktail Trail. Download a digital passport that guides you to seven Downtown Tupelo spots serving up jolly creations. Complete the trail and snag a limited-edition #MyTupelo cocktail shaker to keep the festive spirit flowing!

Tupelo lights up with events and traditions that turn the city into a winter wonderland. Don’t miss the Lighting of Ballard Park, where thousands of glittering lights transform the trees and pathways into a radiant celebration of the season, creating the perfect backdrop for holiday memories with family and friends. Another highlight of the holiday season is the 77th Annual Reed’s Tupelo Christmas Parade, held December 5, from 6-8 p.m., where dazzling floats, festive music, and community cheer come together for a magical evening. This year’s parade invites participants to “Catch the Spirit.”

Just a few blocks away, the Cadence Bank Arena transforms into a holiday skating rink from November 24 through January 4, where all ages can lace up and take a spin beneath the glow of sparkling lights. From December 6–8, the Tupelo Ballet invites audiences to experience its 42nd annual production of “The Nutcracker,” featuring talented pre-professional students, special guest artists, and a live accompaniment by the North Mississippi Symphony Orchestra, bringing Tchaikovsky’s timeless score to life. Over at the historic Lyric Theatre, catch the award-winning community theatre’s performances of “Plaid Tidings,” December 11-13.

Additionally, the North Mississippi Symphony Orchestra presents “Christmas Spirit of Tupelo,” December 13, a joyful concert highlighting the voices of the Itawamba Community College Chorus, Northeast Mississippi Community College Chorus, and the North Mississippi Symphony Orchestra Children’s Chorus. Part of Celebrate Tupelo 2025, these holiday events are the perfect way to soak in the season’s music, magic, and warmth with family and friends.

In Tupelo, the holiday season doesn’t end with Christmas. Keep the celebrations going with the annual Tupelo’s New Year’s Eve Party in Downtown Tupelo. This family-friendly event features a diverse lineup of bands performing on two stages, ensuring there’s something for everyone to enjoy. BankPlus KidsFest kicks off the evening with fun activities for the little ones, while the festivities continue with live music, dazzling fireworks, and a countdown to midnight from the BNA Bank Fairpark Stage. Celebrate the start of 2026 in a safe, vibrant setting filled with music, joy, and community spirit.

Stay connected and make the most of every season in Tupelo! Follow @MyTupelo on Facebook, Instagram, TikTok, YouTube, Pinterest, and X to discover upcoming events, festivals, and local happenings. From seasonal celebrations to outdoor adventures and community experiences, there’s always something new to enjoy in Tupelo.

However you choose to celebrate the holidays, Tupelo offers the perfect blend of festive fun, heartfelt moments, and Southern warmth. Gather your favorite people and let Tupelo show you how magical it feels to slow down, soak it all in, and truly savor the season. Imagine what you can do here!