15 Best Things to Do in Enterprise (AL)

Nestled in the heart of Southeast Alabama, Enterprise might just be the most charming and unexpected destination you’ve yet to discover. Far from a bustling metropolis, this city offers a unique blend of small-town hospitality, fascinating history, and surprising attractions that promise a truly memorable getaway. Known affectionately as the “City of Progress” and famously home to the world’s only monument dedicated to an insect – the Boll Weevil – Enterprise invites you to slow down, explore, and uncover its hidden gems.

Whether you’re a history buff, an outdoor enthusiast, a family seeking fun, or simply looking for a relaxing escape, Enterprise delivers. The best time to visit is during the spring (April-May) or fall (September-October) when the weather is mild and perfect for outdoor activities, though summer brings opportunities for water park adventures. You’ll find a welcoming community ready to share its stories and its distinct Southern charm, making every moment an authentic experience.

Johnny Henderson Family Park

Imagine a sprawling green oasis perfect for families, fitness enthusiasts, and anyone seeking a breath of fresh air – that’s Johnny Henderson Family Park. This expansive park is a true community gem, offering something for everyone across its beautifully maintained grounds. You can spend hours here, whether you’re strolling along the paved walking trails that wind through lush landscapes, letting the kids burn off energy on the state-of-the-art playgrounds, or enjoying a peaceful afternoon by the fishing lake.

The park also features disc golf courses, a splash pad for hot summer days, and numerous picnic areas, making it an ideal spot for a leisurely day out. What makes it special is its sheer variety of amenities, all designed with family enjoyment in mind, providing a safe and vibrant space for recreation and relaxation. It’s a testament to Enterprise’s commitment to its residents and visitors.

Boll Weevil Monument

Prepare to be charmed by the unique and quirky Boll Weevil Monument, a testament to Enterprise’s resilience and gratitude. Erected in 1919, this monument stands proudly in the heart of downtown, celebrating an unlikely hero – or rather, an unlikely catalyst for change. After the boll weevil devastated cotton crops, Enterprise farmers diversified into peanuts and other crops, leading to unprecedented prosperity.

The monument is a whimsical tribute to the insect that inadvertently pushed the community towards agricultural innovation. You’ll find it impossible not to smile as you see the statue of the woman holding the larger-than-life boll weevil. It’s a fantastic photo opportunity and a chance to learn about a fascinating piece of local history that truly defines the spirit of Enterprise. Don’t rush; take a moment to read the inscription and appreciate the story behind this one-of-a-kind landmark.

Lake Tholocco

For those seeking serene waters and outdoor recreation, Lake Tholocco offers a beautiful escape. Located within the Fort Rucker military reservation, this expansive lake provides opportunities for fishing, boating, and enjoying the peaceful natural surroundings. While access requires navigating the base entry procedures, the effort is well worth it for the tranquility you’ll find.

You can rent boats, enjoy a picnic by the shore, or simply relax and take in the scenic views. It’s a popular spot for military families, but also accessible to the public with proper ID and vehicle registration. The lake is known for its clear waters and abundant fish, making it a favorite for anglers. This is a place where you can truly unwind and connect with nature, away from the hustle and bustle.

See a Drive-In Movie

Step back in time for an evening of classic entertainment at a local drive-in movie theater. There’s a unique charm to watching a film under the stars, snuggled in your car with snacks and good company. This nostalgic experience is a fantastic way to spend an evening in Enterprise, offering a blend of retro cool and modern convenience.

You’ll tune your car radio to the movie’s audio, creating a private cinema experience. It’s perfect for families looking for a budget-friendly outing, couples on a unique date night, or solo travelers seeking a dose of Americana. The atmosphere is relaxed and fun, often with double features, making it great value. Make sure to arrive early to get a good spot and soak in the pre-show ambiance.

Depot Museum

Dive into Enterprise’s rich past at the Depot Museum, housed in the beautifully preserved former Louisville & Nashville Railroad Depot. This charming museum offers a captivating glimpse into the city’s history, from its early settlement and agricultural roots to its development into a thriving community. You’ll discover exhibits showcasing vintage tools, household items, photographs, and artifacts that tell the stories of the people who shaped Enterprise.

The building itself is a piece of history, with its classic train station architecture. It’s a wonderful stop for history enthusiasts and curious visitors alike, providing context to the city you’re exploring. The museum operates on donations, making it an accessible and enriching experience for everyone. Allow yourself time to wander through the displays and imagine life in Enterprise decades ago.

Two by Two Petting Zoo

Get up close and personal with a variety of friendly farm animals at Two by Two Petting Zoo. This delightful attraction offers an interactive and educational experience, particularly perfect for families with young children. You’ll have the chance to feed and pet goats, sheep, llamas, and many other charming creatures in a safe and engaging environment.

Beyond the hands-on encounters, the zoo often hosts educational programs and special events, teaching visitors about animal care and farm life. It’s a wonderful way to create lasting memories and introduce children to the wonders of the animal kingdom. The staff are typically very friendly and knowledgeable, enhancing the overall experience. This is more than just seeing animals; it’s about connecting with them in a meaningful way.

Southern Broadway Dinner Theater

Prepare for an unforgettable evening of live entertainment and delicious dining at Southern Broadway Dinner Theater. This unique venue offers professional-quality musical productions and plays, paired with a delightful meal, creating a complete night out. You’ll be treated to a fantastic show performed by talented actors, all while enjoying a multi-course dinner served right at your table.

The ambiance is intimate and engaging, making you feel part of the experience. It’s an ideal choice for couples seeking a romantic night, groups celebrating a special occasion, or anyone who appreciates live theater and good food. Be sure to check their schedule and book tickets in advance, as shows often sell out quickly due to their popularity. This is truly a highlight for Enterprise’s cultural scene.

Pioneer Museum of Alabama

Embark on a journey back in time at the Pioneer Museum of Alabama, located a scenic 45-minute drive from Enterprise in Troy. This expansive outdoor museum brings the 19th-century frontier to life, showcasing authentic log cabins, a grist mill, a blacksmith shop, and a one-room schoolhouse, among other historic structures. You can wander through the village, exploring how early settlers lived, worked, and played.

The museum often features live demonstrations of pioneer crafts and skills, providing an immersive educational experience. It’s a fantastic destination for families, history buffs, and anyone interested in Southern heritage. The sheer scope of the preserved buildings and artifacts makes it a truly unique and enlightening visit. Plan for a few hours to truly explore everything it has to offer.

All About Art

Unleash your inner artist at All About Art, a creative studio where imagination takes center stage. Whether you’re a seasoned artist or a complete beginner, this vibrant space offers a variety of engaging activities like pottery painting, canvas painting, and other craft workshops. You can walk in and choose a piece to paint, or sign up for a guided class to learn new techniques.

It’s a wonderful opportunity to relax, express yourself, and create a unique souvenir of your trip. All About Art is perfect for solo travelers seeking a calming activity, friends looking for a fun outing, or families wanting a creative bonding experience. The friendly staff are always on hand to offer guidance and encouragement, ensuring you leave with a masterpiece you’re proud of.

Historic Rawl’s Hotel

Discover a piece of Enterprise’s elegant past at the Historic Rawl’s Hotel. While no longer operating as a hotel, this beautifully preserved building stands as a grand architectural landmark in the heart of downtown. Built in 1903, it once served as a bustling hub for travelers and local society.

You can admire its stunning Neo-Classical design from the exterior, appreciating its intricate details and imposing facade. The ground floor often houses local businesses or offices, sometimes a charming café, offering a chance to step inside and experience a slice of its historic ambiance. It’s a must-see for architecture enthusiasts and anyone interested in the city’s early 20th-century grandeur. Take a moment to imagine the stories these walls could tell from a bygone era.

Little Red Schoolhouse

Step back into the simple, yet profound, world of early American education at the Little Red Schoolhouse. This charming, one-room schoolhouse is a nostalgic reminder of a time when education was delivered in a very different way. Located within Enterprise, it offers a tangible connection to the past, allowing you to imagine a classroom filled with children of all ages learning together under one teacher.

While it may not always be open for interior tours, its exterior provides a wonderful photo opportunity and a chance to reflect on the evolution of schooling. It’s a small but significant piece of local history, perfect for a quick, contemplative stop. History buffs and those curious about the past will appreciate this quaint landmark.

U.S. Army Aviation Museum

Prepare to be amazed by a world-class collection of military aircraft at the U.S. Army Aviation Museum, located on Fort Rucker. This impressive museum boasts one of the largest collections of helicopters and other military aircraft in the world, tracing the history of Army aviation from its earliest days to modern warfare.

You’ll walk among iconic helicopters like the Huey, Apache, and Chinook, learning about their roles in various conflicts and humanitarian missions. The exhibits are incredibly detailed, featuring interactive displays, artifacts, and personal stories that bring the history to life. It’s a truly captivating experience for aviation enthusiasts, history buffs, and families. Remember that it’s on a military installation, so follow all entry procedures for a smooth visit.

Milky Moo’s

Satisfy your sweet tooth with a visit to Milky Moo’s, a beloved local ice cream parlor that promises a delightful treat for everyone. Known for its extensive menu of unique flavors, sundaes, milkshakes, and other frozen delights, Milky Moo’s is a perfect spot to cool down on a hot day or simply indulge in a delicious dessert. You’ll find classic favorites alongside creative concoctions, ensuring there’s something to tantalize every palate.

The atmosphere is typically vibrant and family-friendly, making it a popular gathering spot. It’s an essential stop for families, couples on a casual date, or solo travelers looking for a sweet pick-me-up. Don’t be surprised if you find yourself wanting to try more than one flavor!

Landmark Park

Venture a short drive to Dothan, Alabama, to explore Landmark Park, a magnificent 100-acre living history farm and natural science education center. This award-winning park offers a captivating blend of history, nature, and wildlife. You can wander through a beautifully preserved 1890s farmstead, complete with historic buildings and farm animals, providing a vivid glimpse into rural life of the past.

Beyond the farm, you’ll discover walking trails through natural habitats, a planetarium, and various exhibits showcasing local flora and fauna. It’s a truly immersive experience for all ages, perfect for families, nature lovers, and history enthusiasts. Plan to spend a good portion of your day here to fully appreciate its diverse offerings.

Water World Water Park

When the Alabama heat calls for a splash, head to Water World Water Park in Dothan, a fantastic destination for family fun. This seasonal water park offers a refreshing escape with its thrilling slides, a relaxing lazy river, a wave pool, and dedicated play areas for younger children. You’ll find plenty of ways to cool off and enjoy an exciting day in the sun.

It’s the perfect place to make a splash and create lasting summer memories, ideal for families and groups of friends. The park provides a safe and supervised environment for aquatic adventures, ensuring a fun day out for everyone. Be sure to check their operating hours, as they are typically seasonal, running from late spring through early fall.

Plan Your Visit

Enterprise, Alabama, truly defies expectations, proving that a small town can offer a wealth of diverse and enriching experiences. From the quirky charm of the Boll Weevil Monument to the tranquil beauty of its parks and the captivating history found in its museums, you’ll discover a destination brimming with character. Whether you’re cheering on a show at the dinner theater, making a splash at a water park, or simply savoring a sweet treat, Enterprise invites you to create unforgettable memories.

This guide provides a roadmap to explore its best attractions and manage your budget effectively. So pack your bags, embrace the Southern hospitality, and prepare to be surprised by the hidden treasures of Enterprise. Your next great adventure awaits!