Events in Enterprise

Signature Events in Enterprise, AL

These events are an expression of our city's unique character, culture, and landmarks. Enterprise is notably known for its Boll Weevil Monument, a tribute to an insect that impacted the economy by destroying cotton crops and forcing farmers to diversify.
Click the button below to see events happening now in Enterprise, AL

World’s Smallest St. Patrick’s Day Parade and .5K Race

March 2024

Enterprise is the official Guinness World Record Holder for the “World’s Smallest Saint Patrick’s Day Parade.

Celtic Highlights Include:

A person of Irish descent, generally dressed in festive garb and carrying a large Irish flag, is the only person in the parade. He, or she, walks one block from the courthouse to the Boll Weevil Monument and back to the courthouse. The parade has enjoyed national, as well as local attention and draws many visitors each year.

An addition was made in 2018 to add the smallest road race, a 0.5K after the parade to keep the small theme going and involve the large crowds who attend the event every year.

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!

The St. Patrick’s Day Parade in Downtown Enterprise is a glorious celebration of Irish heritage, community spirit, and the belief that there’s a little Irish in all of us. So, sport your best green attire, bring along your family and friends, and join us in making this parade a pot of gold at the end of the rainbow!

May the luck of the Irish be with you! 

April Walking Tours

Spring Festival at the Monument

March/April 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 and its forward-thinking dynamism.


  • Blossoming Displays: Marvel at the colorful blooms and themed floral installations that transform Downtown Enterprise into a spring wonderland.
  • Local Art & Crafts: Browse through stalls showcasing the best of local artisans. From handcrafted jewelry to unique home décor, there’s a treasure waiting for every shopper.
  • Live Entertainment: Enjoy an array of performances from local musicians, dancers, and street performers, offering a blend of traditional and contemporary acts.
  • Culinary Delights: Savor mouthwatering treats and seasonal specialties from local food vendors and pop-ups. Whether you crave something sweet or savory, there’s a flavor for every palate.
  • Kids’ Zone: A dedicated space for the little ones with fun rides, interactive games, and workshops to keep them engaged and entertained.
  • Interactive Workshops: Join local experts in hands-on sessions ranging from gardening tips to spring-themed crafts.
  • Historical Walks: Explore the stories behind the Downtown Enterprise landmarks with guided tours and self-led trails.

Organizer’s Note:

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.

Mark your calendars and embrace the joy of spring in the heart of Downtown Enterprise! For further information, ticket bookings, or volunteering opportunities, please contact Main Street Enterprise.

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.


  • Artisan Showcase: Discover a vast array of artworks and crafts ranging from paintings, ceramics, and sculptures to hand-woven textiles and intricate jewelry. Meet the artists behind these creations and perhaps take home a piece that resonates with you.

  • Live Performances: The air will be filled with melodies and rhythms as local musicians, dancers, and theater troupes take to the stage, presenting a rich assortment of performances that cater to all tastes.

  • Culinary Avenue: Taste the flavors of Piney Woods and beyond! From traditional southern treats to modern fusion dishes, our food vendors offer a culinary journey that’s sure to tantalize your taste buds.

  • Interactive Workshops: Dive deep into various art forms with hands-on sessions. Whether you’re a budding artist or just looking for a fun experience, our workshops offer something for everyone.

  • Kids’ Creativity Corner: A special zone dedicated to nurturing the imagination of our younger attendees. With crafts, games, storytelling sessions, and more, it’s a haven of fun and learning.

  • Art Installations: Wander amidst unique and thought-provoking installations set up throughout the campus, each telling a story and inviting reflection.

A Word from the Organizers:

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.

Don’t miss this festival of color, creativity, and camaraderie at the Enterprise State Community College! For more details, donations, or to get involved, please reach out to the Coffee County Arts Alliance.

Festival In The park


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.


  • Nature Trails and Walks: Revel in the beauty of spring with  nature walks, offering insights into the park’s unique flora and fauna.

  • Live Entertainment: Enjoy live entertainment that showcases the best of Enterprise’s local talents.

  • Art and Craft Market: Wander through rows of stalls brimming with handcrafted goods, artisanal products, and unique trinkets, each telling a story of passion and creativity.

  • Food Fiesta: Relish a spread of mouthwatering delights, from classic park snacks to gourmet dishes, curated by local vendors and chefs.

  • Kids’ Adventure Land: A dedicated playground of fun, learning, and laughter. Watch as the young ones enjoy playing, face painting, and a host of interactive games.

  • Fireworks Show: Light up your night with the Spectacular Skyfire, a dazzling display of pyrotechnics that promises to leave you in awe! Witness the night sky burst into a kaleidoscope of colors as synchronized fireworks dance to the rhythm of an enchanting soundtrack. A perfect blend of art and science, this show is more than just an event—it’s a celestial celebration that brings together the community under a canopy of shimmering lights.

Message from the Organizers:

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.

Gear up for an unforgettable day at Johnny Henderson Family Park. For more information, volunteer opportunities, or any inquiries, please get in touch with the Enterprise Parks and Recreation Department.

Peak Season Day at the Farmers Market

May 2024

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.


  • Fresh Produce Galore: Feast your senses on a vibrant array of fruits, vegetables, herbs, and more, all freshly picked and presented by our dedicated local farmers.

  • Artisanal Showcase: Discover handcrafted cheeses, homemade jams, baked goods, and other gourmet delights that promise to tantalize your taste buds.

  • Live Cooking Demos: Join local chefs as they whip up seasonal dishes right before your eyes, sharing their secret recipes and cooking tips.

  • Crafts & Handmade Goods: Beyond edibles, browse stalls that offer handcrafted jewelry, pottery, textiles, and more, each with its own unique story.

  • Interactive Workshops: Engage in sessions that range from organic farming practices to DIY crafts, promoting sustainable and self-reliant living.

  • Live Entertainment: Enjoy foot-tapping tunes and performances by local artists, creating the perfect ambience for a day out in the market.

  • Kids’ Agri-Zone: A special corner dedicated to the young ones, where they can learn about farming, plant seeds, and even meet some farm animals.

A Note from the Organizers:

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

Boll Weevil Fall Festival

October 21, 2023

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.

Event Highlights:

  •  Shop Local: Discover unique finds from local artisans, boutiques, and shops. Take advantage of exclusive offers and promotions available only during this event!

  •  Taste of Enterprise: Savor mouth-watering dishes and beverages from local eateries and pop-up stalls, celebrating the diverse culinary heritage of our community.

  •  Art Walk: Admire the works of local artists, from paintings and sculptures to live performances and interactive installations.

  •  Live Music & Entertainment: Multiple stages will host a variety of genres, spotlighting local talent and ensuring there’s a beat for every foot.

  •  Historical Tours: Dive deep into the roots of Enterprise with guided tours highlighting our town’s history, architecture, and fascinating stories.

  •  Family Fun Zone: A dedicated space for families with kids’ activities, interactive games, and special entertainment to keep the little ones engaged.

  •  Networking Hub: Connect with local businesses, entrepreneurs, and community leaders. An opportunity to foster collaborations and deepen your ties within the Enterprise community.

  •  Pop-Up Parks: Temporary green spaces with seating, creating pockets of relaxation amidst the bustling event.

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.  Downtown awaits you. Let’s make memories together! 

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.

Highlights Include:

  •  Pumpkin Patch: Choose your perfect pumpkin from a sea of orange, ideal for jack-o’-lanterns, fall decorations, or your favorite pumpkin pie recipe.

  •  Pumpkin Treats: Local vendors will offer an array of pumpkin-inspired delicacies, from pies and pastries to savory dishes.

  •  Craft Corner: Engage in pumpkin-decorating contests, craft booths, and more for all ages.

  •  Live Entertainment: Enjoy the sounds of the season with local musicians setting the festive mood.

  •  Autumn Vendors: Explore stalls brimming with fall produce, crafts, and other seasonal goodies.

  •  Kids’ Zone: A special area dedicated to the youngest visitors, packed with fun games, face painting, and a mini hayride.

  •  Farmers Market Favorites: 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! 

Spooky in the Park

October 27, 2023

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, is your passport to a spine-tingling, yet family-friendly, Halloween extravaganza.

Spectacular Features:

  • Haunted Hayrides: Embark on a moonlit journey, filled with eerie tales and unexpected encounters. Hold on tight!

  • Trick or Treat Trail: Wander along the well-lit paths and collect treats from friendly (and sometimes spooky) characters stationed at intervals.

  • Costume Parade: Show off your spookiest, funniest, and most inventive costumes. Prizes await for the best-dressed!

  • Campfire Ghost Stories: Gather around the flickering flames and get ready for some legendary local ghost tales. Don’t forget to bring a blanket!

  • Creepy Cinema: Pull up a patch of grass and enjoy classic Halloween films on a giant outdoor screen.

  • Monster Mash Dance Party: Groove to the bewitching beats, as our DJ spins a mix of classic and contemporary hits.

  • Witchy Workshops: Craft stations for potion-making, broom designing, and other spooky creations.

  • Ghoul Grub: A variety of food trucks and stalls will serve up both Halloween-inspired treats and classic park favorites.

  • Kiddie Corners: For our youngest ghouls and boys, a dedicated play area with age-appropriate games, storytelling, and face painting.

“Spooky in the City” is 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.  Gather your coven, summon your spirits, and join us for a night that promises to be hauntingly unforgettable. See you if you dare!

Enterprise Christmas Parade

November 30, 2023

(Organized by: City of Enterprise)

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.

Festive Highlights Include:

  • Santa’s Grand Arrival: The star of the evening, Santa Claus, makes his joyful journey through Downtown Enterprise, waving to the crowds and heralding the official start of the holiday season.

  • Marching Bands: Local schools and community groups showcase their talent, playing beloved Christmas carols and filling the streets with rhythmic beats and melodies.

  • Festive Floats: Witness a spectacle as businesses, schools, and community organizations present intricately designed floats, each telling its own Christmas story.

  • Street Performers: Elves, snowmen, and other festive characters interact with the crowds, offering both entertainment and plenty of photo opportunities.

  • Live Caroling: Choirs and singing groups serenade spectators with heartwarming renditions of holiday classics.

  • Holiday Treat Stations: Warm up with hot cocoa, nibble on gingerbread cookies, and savor other holiday treats offered by local vendors.

  • Shops and Boutiques: 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! 

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!

Fantastical Features Include:

  • Whoville Town Square: Experience a replica of the iconic Whoville square, complete with candy-striped poles, snow-capped rooftops, and jubilant Whos ready to greet you.

  • Whoville Characters Meet & Greet: Rub shoulders with the Grinch himself, share a laugh with Cindy Lou Who, and snap photos with the jubilant residents of Whoville.

  • Whosical Performances: Join in as the town gathers for live renditions of classic songs from the tale, including the evergreen “Welcome Christmas.”

  • Who-Feast Food Stalls: Taste delectable treats inspired by the Seussian world – from roast beast to who-pudding and rare Who-roast beast.

  • Whoville Market: Explore stalls brimming with quirky gifts, Seussian crafts, and Grinchy goodies.

  • Crafty Who-Corner: Kids and adults alike can dive into fun DIY projects, making their very own Whoville-inspired crafts and ornaments.

  • Storytime with Cindy Lou Who: Gather around as Cindy Lou recounts the heartwarming tale of how the Grinch discovered the true spirit of Christmas.

  • Grinch’s Lair: Dare to venture into the Grinch’s mountain hideaway? Get a glimpse into his mischievous plans and maybe, just maybe, help him find his holiday spirit.

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.

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.

Event Highlights Include:

  • The Lighting Ceremony: Witness the moment of magic as the towering Christmas tree at City Hall comes alive with thousands of twinkling lights, casting a warm and radiant glow over all in attendance.

  • Live Caroling: Let the harmonious voices of local choirs serenade you with classic yuletide melodies, rekindling beloved holiday memories.

  • Warm Refreshments: Warm your hands and hearts with complimentary cups of hot cocoa and mulled cider, perfectly capturing the essence of the season.

  • Festive Performances: Enjoy a line-up of local performers showcasing festive dances, skits, and songs, each echoing the joyous themes of the holiday season.

  • Santa’s Visit: The jolly old man himself graces the occasion, listening to children’s wishes and spreading his infectious Christmas cheer.

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.