Events in Enterprise
Signature Events in Enterprise, AL
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World’s Smallest St. Patrick’s Day Parade and .5K Race
March 2024
(Organized by: Enterprise Chamber of Commerce)
Enterprise is the official Guinness World Record Holder for the “World’s Smallest Saint Patrick’s Day Parade.”
The parade has enjoyed national, as well as local attention and draws many visitors each year.
In 2018 we added the world’s smallest road race, a 0.5K after the parade.
Downtown Enterprise is set to don a vibrant shade of green this March, as the annual St. Patrick’s Day Parade marches through its historic streets. 
Organized by the Enterprise Chamber of Commerce, this spirited event promises to paint the town not just green, but also gold, orange, and every hue of Irish pride!
April Walking Tours
Spring Festival at the Monument
April 13, 2024
(Organized by: Main Street Enterprise)
Celebrate the spirit of renewal and the beauty of the season at the annual Spring Festival at the Monument! Set against the historic backdrop of Downtown Enterprise, this vibrant festival promises a delightful mix of traditional and contemporary festivities. Brought to you by Main Street Enterprise, the event is a testament to the community’s rich heritage.
Browse vendors showcasing the best of local artisans. From handcrafted jewelry to unique home décor, there’s a treasure waiting for every shopper. Enjoy an array of performances and contests. Savor mouthwatering treats and seasonal specialties from local food retaurants and food truck vendors. Whether you crave something sweet or savory, there’s a flavor for every palate. The little ones will enjoy fun activities, and interactive games.
Main Street Enterprise is proud to bring the community together for this annual celebration. The Spring Festival at the Monument is not just an event; it’s a reflection of the community’s heart, spirit, and vibrancy. We invite residents and visitors alike to join us in making memories that last a lifetime.
Piney Woods Arts Festival
April 20-21, 2024
(Organized by: Coffee County Arts Alliance)
Step into a world of creativity and culture at the CCAA Piney Woods Arts Festival! Hosted by the Coffee County Arts Alliance, this annual gathering at the Enterprise State Community College brings together a diverse tapestry of artists, crafters, performers, and enthusiasts. It’s an exquisite blend of tradition and innovation, honoring the deep-rooted artistic heritage of the Wiregrass region while also celebrating contemporary expressions from all over the Southeast.
Hosting more than 75 arts and craft vendors. This is a juried art contest. The air will be filled with melodies and rhythms as local musicians, dancers, and theater groups take to the stage, presenting a rich assortment of performances that cater to all tastes. Food vendors offer a culinary journey that’s sure to tantalize your taste buds. Our younger attendees enjoy crafts, games, storytelling sessions, and more, it’s a haven of fun and learning.
The Coffee County Arts Alliance is deeply committed to fostering artistic expression and appreciation within our community. The Piney Woods Arts Festival is a testament to this mission, and we’re thrilled to present an event that shines a spotlight on both emerging and established talents. We warmly invite everyone, from near and far, to join us in this celebration of art, culture, and community spirit.
Festival In The park
May 4, 2024
Experience the magic of community spirit and the great outdoors at the annual Festival in the Park! Nestled within the lush greens and serene ambiance of Johnny Henderson Family Park, this event is a joyful embrace of nature, local culture, and the vibrant life of Enterprise. Spearheaded by the Enterprise Parks and Recreation Department, this festival is more than just a day in the park—it’s an affirmation of the unity, diversity, and vibrancy of our community.
Revel in the beauty of of the park with nature walks, offering insights into the park’s unique flora and fauna.
Enjoy live entertainment that showcases the best of Enterprise’s local talents.
Kids enjoy the playground and splash pad. Watch as the young ones enjoy playing, face painting, and a host of interactive games. Light up your night with the Spectacular Firework Show!
The Enterprise Parks and Recreation Department is elated to invite everyone to Festival in the Park—a day to reconnect with nature, bond with loved ones, and celebrate the essence of community. Let’s come together to make memories, enjoy the simple pleasures of life, and cherish the natural beauty around us.
Peak Season Day at the Farmers Market
May 2024
(Organized by: Enterprise Farmers Market)
Welcome the bounty of the season at the Farmers Market Peak Season Kickoff! Hosted at the heart of the community, the Enterprise Farmers Market is all set to unveil the freshest and finest produce, artisanal goods, and local treasures. Celebrating the peak of harvest season, this special kickoff promises a medley of flavors, colors, and experiences, reflecting the rich agricultural heritage of our region and the passion of our local farmers and artisans.
Feast your senses on a vibrant array of fruits, vegetables, herbs, and more, all freshly picked and presented by our dedicated local farmers. Discover handcrafted cheeses, homemade jams, baked goods, and other gourmet delights that promise to tantalize your taste buds. Join local chefs as they whip up seasonal dishes right before your eyes, sharing their secret recipes and cooking tips.
The Enterprise Farmers Market is more than a trading spot—it’s a community hub, a place where connections are forged over the shared love for fresh, local produce and artisanal creations. As we usher in our peak season, we invite everyone to come and celebrate the hard work, dedication, and love that goes into every product you find here. Let’s support local, eat healthy, and foster community spirit!
Watermelon Day at the Farmers Market
June 2024
Pumpkin Day at the Farmers Market
October 14, 2023
(Organized by: Enterprise Farmers Market)
Celebrate the magic of fall with Pumpkin Day at the Enterprise Farmers Market! As the leaves turn to their autumnal shades, the market transforms into a pumpkin wonderland, offering a delightful spread of pumpkin-themed activities, treats, and treasures.
Choose your perfect pumpkin from a sea of orange, ideal for jack-o’-lanterns, fall decorations, or your favorite pumpkin pie recipe. Local vendors will offer an array of pumpkin-inspired delicacies, from pies and pastries to savory dishes. Engage in pumpkin-decorating contests, craft booths, and more for all ages.
As always, our beloved local vendors will be showcasing their freshest produce, artisan goods, and more.
Come dressed in your coziest fall attire and celebrate the beauty and bounty of the season with friends, family, and the Enterprise community.
Whether you’re on the hunt for the perfect pumpkin, craving delicious fall treats, or simply looking to soak in the festive atmosphere, Pumpkin Day promises a memorable experience for all.
See you at the market!
Boll Weevil Fall Festival
October 21, 2023
(Organized by: Enterprise Chamber of Commerce)
Step into the heart of Enterprise on October 21st for a vibrant celebration of our community’s rich history, culture, and thriving local businesses. Downtown Enterprise Celebration, brought to you by the Enterprise Chamber of Commerce, aims to showcase the best our town has to offer in a lively and welcoming atmosphere.
This downtown Street Event hosts more than 100 vendors, food trucks, music, kids’ activities, interactive games, and more.
Connect with local businesses, entrepreneurs, and community leaders. An opportunity to foster collaborations and deepen your ties within the Enterprise community.
Downtown Enterprise Celebration is more than just an event; it’s a testament to the spirit, unity, and progress of our community. Join hands with fellow residents, visitors, and business owners to relish in a day of fun, learning, and deep-rooted community pride.
Spooky in the Park
October 27, 2023
(Organized by: Enterprise Parks and Recreation Department)
As the mist descends and shadows lengthen, Johnny Henderson Family Park transforms into the epicenter of chills and thrills. Curated by the Enterprise Parks and Recreation Department, this is your passport to a spine-tingling, yet family-friendly, Halloween extravaganza.
Wander along the well-lit paths and collect treats from friendly (and sometimes spooky) characters stationed at intervals.
Show off your spookiest, funniest, and most inventive costumes. Prizes await for the best-dressed.
Designed to deliver the perfect blend of delightful scares, enchanting activities, and memory-making moments. Whether you’re a thrill-seeker, a Halloween enthusiast, or just looking for a magical evening with loved ones, there’s something for everyone. See you if you dare!
Enterprise Christmas Parade
November 28, 2023
(Organized by: Enterprise Chamber of Commerce
The festive season begins in style with the beloved Enterprise Christmas Parade, illuminating the historic streets of Downtown Enterprise. Hosted by the Enterprise Chamber of Commerce, this annual tradition promises a magical evening filled with twinkling lights, joyful music, and the undeniable warmth of community spirit.
Santa Claus, makes his joyful journey through Downtown Enterprise, waving to the crowd. Local schools and community groups showcase their talent, playing beloved Christmas carols and filling the streets with rhythmic beats and melodies. Witness a spectacle as businesses, schools, and community organizations present intricately designed floats, each telling its own Christmas story. Many downtown businesses extend their hours for the parade, inviting visitors to commence their holiday shopping or simply browse the festively adorned windows.
The Enterprise Christmas Parade is more than just an event; it’s a cherished gathering that brings families, friends, and neighbors together, celebrating the joy, hope, and love that the season embodies. So, wrap up warm, grab a mug of something hot, and immerse yourself in the enchanting world of Downtown Enterprise‘s Christmas celebration.
See you under the glow of holiday lights!
Enterprise Christmas Tree Lighting
November 30, 2023
City Hall
(Organized by: City of Enterprise)
Gather under the wintry skies as the heart of the City of Enterprise prepares to shimmer and shine! The annual Enterprise Christmas Tree Lighting at City Hall is not merely a ceremony but a cherished occasion, encapsulating the community’s collective spirit, hope, and festive cheer.
Witness the moment of magic as the towering Christmas tree comes alive with thousands of twinkling lights, casting a warm and radiant glow over all in attendance. Let the harmonious voices of local choirs serenade you with classic yuletide melodies, rekindling beloved holiday memories.
The Enterprise Christmas Tree Lighting is a testament to the city’s unity, hope, and festive spirit. As the lights of the tree mirror the stars above, let’s come together to celebrate the season’s promise, share in its joy, and create memories that will be cherished for years to come. Join us at City Hall, and be a part of this luminous tradition.
Whoville Wholiday Celebration
December 2, 2023
(Organized by: Main Street Enterprise)
Step into the whimsical world of Dr. Seuss as Downtown Enterprise is transformed into the delightful town of Whoville! Presented by Main Street Enterprise, the Whoville Celebration offers an enchanting escape into the pages of “How the Grinch Stole Christmas!” Come, and let your heart grow three sizes with joy and festivity!
Experience a replica of the iconic Whoville square, complete with jubilant Whos ready to greet you. Rub shoulders with the Grinch himself, share a laugh with Cindy Lou Who, and snap photos with the jubilant residents of Whoville.
The Whoville Celebration is a heartwarming reminder that Christmas doesn’t come from a store; perhaps, it means a little bit more. Whether you’re a fan of Dr. Seuss, or simply looking for a unique and magical way to usher in the holiday season, Downtown Enterprise‘s Whoville is the place to be.
Join us in Whoville, where every Who down in Whoville, the tall and the small, will be celebrating with great joy and jubilation.
