Girls Night Out Round Up 2026
The Annual Girls Night Out event is focused on providing LOCAL Breast Cancer Support Services. Proceeds from the event will be administered through Coffee County Family Services to individuals in our community battling Breast Cancer who need support services assistance including co-pays, transportation, childcare, drug coverage, groceries, and personal comfort needs such as wigs and head coverings.
650 Advanced Tickets will be sold 8/3/2025 through 9/25/2026 for $25 WHILE SUPPLIES LAST and will include a Girls Night Out Roundup Swag Bag. Tickets will be available for presell through participating merchants who will have a pink cowboy hat on the storefront beginning Monday, August 3, 2026.
We will also be offering an official Girls Night Out Round Up T-Shirt available for purchase via PRE-ORDER for the Event. DEADLINE for T-SHIRT PREORDERS is 9/11/2026. Click the ORDER A T-SHIRT button to place your order. All proceeds from the T-SHIRT sales will fund the event donation.
If you are unable to attend the event but would like to support this worthy cause in our community, please click the DONATION button.
PINK RIBBON ROUND UP 5K and FUN RUN
THANK YOU TO Brightspeed Fiber Internet our Primary Sponsor for the Pink Ribbon Roundup 5K and FUN RUN!
Enterprise Parks and Recreation Department is joining the fun and partnering with the Downtown Enterprise Business Association-Friends of Main Street to host a Pink Ribbon Round Up 5K and FUN RUN to benefit Breast Cancer Support Services in our community.
Hometown Heroes Celebration - A Salute to our Military and First Responders
THANK YOU TO OUR PRIMARY 5K FUN RUN SPONSOR!
THANK YOU TO OUR PET CONTEST SPONSOR!
Hometown Heroes Celebration 5K & Fun Run
A Salute to Our Military & First Responders
Join us in beautiful downtown Enterprise on Saturday, June 6, 2026, at 8:00 AM for the Hometown Heroes Celebration 5K & Fun Run — a special community event honoring the brave men and women who serve as military members, veterans, law enforcement officers, firefighters, EMS personnel, and first responders.
Bring the whole family out for a morning of patriotism, fitness, and community spirit as runners and walkers of all ages come together to celebrate our hometown heroes. Whether you are racing for a personal best or participating in the fun run with friends and family, this event is designed for everyone to enjoy. All proceeds from the event will benefit scholarships for dependents of military and first responders, helping support the families of those who dedicate their lives to protecting and serving our communities.
Event Details
Date: Saturday, June 6, 2026
Time: 8:00 AM
Location: Downtown Enterprise
Events: 5K Race & Family Fun Run
Registration: Register and pay online using the links below through Square secure payment buttons below. PAST PRE-REGISTRATION DEADLINE - ON SITE REGISTRATION WILL BE AVAILABLE BEGINNING AT 7:15 AM CREDIT OR DEBIT CARD PAYMENT WILL BE ACCEPTED
Come run, walk, cheer, and celebrate the heroes who make our communities safer every day. Together, we can honor their service and support the next generation through scholarship opportunities.
PATRIOTIC PET CONTEST!
Get ready for wagging tails, creative costumes, and a whole lot of personality — welcome to our PATRIOTIC PET CONTEST! Our Patriotic Pet Contest is sponsored by Wiregrass Home Team where they provide their available resources at top quality level and share their specialized knowledge in residential and commercial sales… always focused on the CLIENT. Each pet will come across the stage with their owner, show off their patriotic look, and give us their best strut, pose, or tail wag.
Our judges are watching closely for:
• Creativity
• Crowd appeal
• Overall patriotic spirit
We will have awards in all three categories for two divisions (Small Dog and Large Dog) AND we will have one for overall Crowd Favorite.
Event Details
Date: Saturday, June 6, 2026
Time: TBD
Location: Downtown Enterprise
Events: Patriotic Pet Contest
Registration: Register for FREE online using the button below.
Hometown Heroes Scholarship Program
The Hometown Heroes Scholarship is sponsored by DEBA Friends of Main Street, a 501c3 organization, through proceeds from the Hometown Heroes Celebration and philanthropy funds designated by DEBA FOM. Scholarships are intended to assist dependents of Military Personnel and First Responders who plan to attend Enterprise State Community College.
APPLICATION DEADLINE
All applications must be received no later than July 15, 2026.
SCHOLARSHIP AWARD DATE
Scholarship recipients will be notified and awards announced on August 1, 2026. Scholarship awards will range from $1000 - $4000 based on the proceeds from the Hometown Heroes Celebration and matching funds from the Downtown Enterprise Business Association – Friends of Main Street, a 501c3 Organization.
ELIGIBILITY REQUIREMENTS
Applicants must:
· Be a dependent of an Active Duty, Reserve, National Guard, Retired, or Veteran Military Service Member; OR
· Be a dependent of a First Responder (Law Enforcement, Firefighter, EMS, Emergency Communications/Dispatch, or Rescue Personnel).
· Be accepted to or enrolled at Enterprise State Community College.
· Submit a complete application by the deadline.
Girls Night Out 2025
The Downtown Enterprise Business Association/Friends of Main Street and Main Street Enterprise are excited to host our annual Girls Night Out for Breast Cancer Awareness, Saturday, September 27, 2025, 3pm-7pm. The annual fundraising event provides an opportunity to explore the fabulous Downtown Enterprise District, while raising funds to provide Breast Cancer Support Services in our local community. Proceeds from the event will be administered through Coffee County Family Services to provide support services specifically to those in our area facing breast cancer challenges. We are excited to have 26 Downtown Merchants Participating and 9 sponsors for the event including Visit Enterprise, Corks and Cattle, River Bank, Southeast Health, Edward Jones, Medical Center Enterprise, Restoration Dental, Five Star Credit Union and Dayspring Hospice. 500 Tickets will go on sale August 13, 2025 for $20 each while supplies last. Supporters of the event may buy tickets at participating Pink Ribbon retailers which will provide them with a Swag Bag and Downtown Passport to visit participating merchants and be entered into Mega Prize Basket Drawings. We were honored to donate $7000.00 in 2024 to Coffee County Family Services which has been essential in providing advocacy, education and support for those needing Breast Cancer assistance in our community. We look forward to exceeding that goal in 2025!
Tax Free Frenzie
Enjoy Alabama's Sales Tax-Free Weekend in Downtown Enterprise! Alabama’s 19th annual sales tax holiday for school-related items begins at 12:01 a.m. Friday, July 18, 2025, and ends at midnight Sunday, July 20, 2025, giving shoppers the opportunity to purchase certain school supplies, computers, books and clothing free of the state’s four percent sales or use tax. We encourage citizens to shop local this tax-free weekend!
Enterprise Farmers Market Watermelon Day
Celebrate the sweetness of summer at Watermelon Day at the Farmers Market! Join us for a juicy, fun-filled event featuring fresh, locally grown watermelons, delicious recipes, and exciting giveaways. Perfect for the whole family, it’s a refreshing way to support local farmers and savor the best of the season. Don’t miss out on watermelon tastings, fun activities, and a chance to pick up your favorite slices straight from the farm!
Piney Woods Arts Festival
This event is fun for all ages and boasts local shopping, food trucks, live music and more! FREE activities will be available throughout event grounds including train rides, inflatables and more!
Peak Season Kick Off at the Farmer's Market
Join us for a fresh and fun experience at the Enterprise Farmers Market Peak Season Kickoff, Saturday, June 1, 2024 from 7 a.m. to Noon at 525 N. Main Street. Because of inclement weather, this event has been moved from its original date of May 18 to June 1, but we plan to have the same great activities
Military, Mutts & Music
Join us in the heart of Downtown Enterprise for a community celebration that honors our military heroes, showcases our four-legged friends, and brings the streets alive with music! Military, Mutts, and Music is a family-friendly event filled with live performances by local musicians, dog-friendly activities, vendors, and patriotic pride.
Festival in the Park
SAVE THE DATE: The 26th Annual Festival in the Park is set for Saturday, May 3, 2025, from 3-8pm/dark at Johnny Henderson Family Park. 🎆
Spring Showcase at the Monument
This event is fun for all ages and boasts local shopping, food trucks, live music and more! FREE activities will be available throughout event grounds including train rides, inflatables and more!
Easter at the Market
About the Enterprise Farmers Market
Come and taste real flavors, support our farmers, enjoy the season, connect with your community and discover the satisfaction of networking with local farmers and cooking homegrown foods for your family.
Market days for the Enterprise Farmers Market are Tuesday, Thursday and Saturday from 7 a.m. until 11 a.m. Market hours may be extended on special event days.
The Market is open year-round when fresh, seasonal items are available. The peak season for the quantity and variety of fruits and vegetables is April through August but fall and winter produce is often available.
For more information, call Birgit Briggs, Market Manager, at 334-348-2668.
Available items
Listed below are produce items and canned goods that are available at the Farmers Market during various times of the year:
Beans, Blueberries, Boiled Peanuts, Cabbages, Corn-on-the-Cob, Cucumbers, Eggplants, Herbs and Herb Products, Home-Baked goods, Homemade Jams and Jellies, Honey, New Potatoes, Onions, Peas, Plants and Flowers, Radishes, Squash, Tomatoes, Watermelons and more!
LEARN MORE from our Partner, The City of Enterprise, Alabama
