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Whether you’re searching for things to do in Fredericktown MO this weekend or planning ahead for spring events in Southeast Missouri, the Fredericktown Azalea Festival 2026 should be at the top of your list.
This annual tradition brings together live music, competitions, community events, and local vendors for one unforgettable weekend. With three full days of activities, it’s one of the largest and most anticipated festivals in the region.
This guide covers everything you need to know about the Fredericktown Azalea Festival 2026, including events, schedules, vendors, and what to expect throughout the weekend.
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Date:May 1–3, 2026
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Location:Fredericktown, Missouri
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Red, White, andBloom Theme
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Events, Vendors, Competitions
🎉 Fredericktown Azalea Festival Highlights & Events
The Fredericktown Festival features a packed schedule of:
- 🎶 Live music all weekend
- 🎉 Community events & games
- 🐾 Pet show & family contests
- 👶 Baby contest & diaper derby
- 🚗 Full parade through downtown
- 🛍️ Massive vendor marketplace
- 🏆 Tournaments & competitions
- 🍴 Food vendors & local favorites
👉 Be sure to arrive early — many events and competitions have specific start times and registration deadlines.
🎶 2026 Live Music Lineup (Main Stage Schedule)
One of the biggest draws of the festival is the live music lineup, featuring regional favorites performing all weekend long. From daytime acoustic sets to high-energy evening performances, there’s music happening throughout the entire weekend.
Friday, May 1
🕔 5:00 PM – 10:00 PM → Blackbird Strut Band
Saturday, May 2
🕔 10:00 AM – 1:00 PM → Amaryllis
🕔 2:00 PM – 6:00 PM → Justin Heskett Band
Sunday, May 3
🕔 10:00 AM – 2:00 PM → Darren Thomas
🕔 3:00 PM – 6:00 PM → Jordon Voss & David Kelly
🎉 Parade, Contests & Community Favorites
Some of the most loved traditions at the Fredericktown Azalea Festival are the parade, contests, and community events. These are the moments that truly bring the town together—and in 2026, they’re packed with activity.
The annual parade is one of the biggest highlights of the entire weekend.
📅 Date: Sunday, May 3, 2026
🕙 Time: 2:00 PM
📍 Location: Downtown Fredericktown (Main Street route)
🎉 Theme: Red, White, and Bloom (celebrating America’s 250th anniversary)
What to Expect:
- Local businesses and organizations
- Decorated floats and themed entries
- Community groups and performers
👉 Entry Info: Parade entries are open to businesses, organizations, and individuals (registration required in advance through festival organizers).
- Register by Tuesday, April 21, 2026
- Text or Email Marissa
- (573)783-9951
- Mmh9951@gmail.com
💲 Cost:
- Free
💡 Pro Tip: Plan to arrive at least 30–45 minutes early to secure a good viewing spot—this is one of the busiest events of the weekend.
👶 Cutest Baby Contest (2026 Details)
A long-standing tradition that celebrates the youngest members of the community.
📅 Date: Saturday, May 2, 2026
🕒 Voting Booth Open: 10:00 AM – 5:00 PM
📍 Location: Festival stage / designated judging area
Participation Details:
- Open to babies under 1 – should not turn 1 before May 1, 2026
- Must be a resident of Madison County
- Judged on appearance, personality, and presentation
- Winner will be selected and announced Saturday, May 2, 2026
- For more information, contact Carol King at (573) 450-8881
👉 Registration:
- Applications must be received by Friday, April 24th, 2026
- Mail Applications to: Nu Zeta Sorority, 1341 Madison 205 Fredericktown, MO 63645
- Enclose a 4 X 6 Color Photo with application
💲 Cost:
- $1 Entry Fee
This event draws a large crowd and is a favorite for families attending the festival.
🏃♂️ Azalea Festival 5K Run & 1-Mile Walk
One of the festival’s staple events is the Azalea Festival 5K Run & 1-Mile Walk, open to all ages and skill levels.
📅 Date: Saturday, May 2, 2026
🕙 Registration: 7:00 AM – 7:45 AM
🕙 Race Start: 8:00 AM
📍Location: East Main & South Mine La Motte (Liberty Hall / Wilson Funeral Home Basement area)
👉 Registration:
- For more information contact Brandon Hale at (573) 701-5844 or Marissa Hale at (573) 783-9951.
- Registration forms can also be mailed to: Brandon Hale at 1479 Hwy 00, Fredericktown, MO 63645 or dropped off at New Era Bank – 101 South Mine La Motte Fredericktown, MO 63645
💲Cost & Perks:
- $10 entry (pre-registration or day-of)
- First 60 participants receive a t-shirt
Whether you’re running competitively or just enjoying a morning walk, this event is a great way to start your festival day.
🍼 Diaper Derby & Decorated Diapers
One of the most entertaining and crowd-loved events of the weekend.
📅 Date: Saturday, May 2, 2026
🕓 Begins at: 10:00 AM
📍 Location: Azalea Park Festival Grounds between the rides and crafts.
How It Works:
- Babies crawl toward a finish line
- Parents encourage (but don’t touch!)
- Babies must be UNDER 1 Year of age by May 2, 2026
- Babies can also participate in the Best “festival themed” decorated diaper contest as well
👉 Registration:
- Same-day sign-up prior to the event by 9:45 AM
💲 Cost:
- Free
💡 Tip: Bring something that will grab your baby’s attention (toy, phone, etc.) to help guide them!
🐾 Pet Show
The Pet Show is one of the most fun and lighthearted events at the festival.
📅 Date: Saturday, May 2, 2026
🕐 Time: 11:00 AM
📍 Location: Azalea Park Festival grounds (Bill Whitener Pavillion)
Participation Details:
- Open to a variety of pets
- Multiple Judging Categories
- Keep in Mind – No animals on festival ground except with 30 minutes before and after Pet Show
👉 Registration: On-site prior to event start (arrive 15-20 minutes early)
💲 Cost:
- $1 entry fee
This is a great event whether you’re entering or just watching—expect lots of laughs and creative entries.
Start your Saturday morning with a local favorite — the Annual Azalea Breakfast, hosted by the Fredericktown FFA Alumni.
📅 Date: Saturday, May 2
🕙 Time: 6:30 AM – 10:00 AM
📍Location: Fredericktown United Methodist Church – 216 S Main St, Fredericktown, MO 63645
💲Cost:
- $10 per person
- Kids 5 and under eat FREE
🎯 Proceeds benefit Fredericktown FFA Alumni for future scholarships and events, making this a great way to support the community while enjoying a hearty breakfast.
🎯 Community Games & Activities (All Weekend)
In addition to scheduled events, there are ongoing activities happening throughout the festival.
📅 Dates: May 1–3, 2026
📍 Location: Festival grounds throughout downtown
What You’ll Find:
- Kids’ games and activity booths
- Interactive family-friendly events
- Community-led activities and entertainment
These are perfect for filling in time between larger events and making sure there’s always something to do.
👉 Looking for other local events in Southeast Missouri? Check out our local events guide!
🏆 Tournaments & Competitions
If you’re looking to compete (or just enjoy the action), the Azalea Festival also features a full lineup of tournaments and competitions throughout the weekend.
📅 Date: Friday, May 1, 2026 – Sunday, May 3, 2026
🕘 Time: Begins at 9:00 AM
📍 Location: Fredericktown High School – 805 MO-72, Fredericktown, MO 63645
📝 Details:
- 5 players per team max
- 3 game guarantee
- Divisions based on age groups
👉 Registration:
- Pre-registration required
- Online Registration: Sign Up Here
- Register By Email: Send Request
💲 Cost:
- $100 per team
📅 Date: Saturday, May 2, 2026
🕘 Check In & Warm Up: Starts at 8:00 AM
🕘 Tournament Play Begins: Starts at 9:00 AM
📍 Location: Rockwall Pickleball Courts – 601 Benson St Fredericktown, MO 63645
📝 Details:
- Doubles Round Robin format
- Skill level & Gender Brackets
👉 Registration:
- Advance sign-up required – Last day to Register is Thursday, April 30th, 2026.
- For questions or to register please contact Mark Hovis at (573) 783-9911
💲 Cost:
- $40 per team
📅 Date: Saturday, May 2, 2026
🕗 Registration: 7:00 AM
🕗 Tee Off: 8:00 AM
📍 Location: Cherrywood Farm & Golf Club – 1157 Madison 502, Fredericktown, MO 63645
📝 Details:
- Two Man Scramble
- 18 Holes
- Cash Prizes
👉 Registration:
- Required in advance – Call for more details: (573)783-0012
💲 Cost:
- $130 entry fee
📅 Date: Saturday, May 2, 2026
🕙 Check In: 8:45 AM
🕙 Start Time: 9:00 AM
📍 Location: Azalea Park in Fredericktown
📝 Details:
- Must be at least 15 years old to play
- Cash Prize for Winning Team
👉 Registration:
- Must be signed up by April 30th
- Message Carson at (573) 934-1762 to sign up
💲 Cost:
- $60 per team
📅 Date: Saturday, May 2, 2026
🕛 Time: Starts at 10:00 AM
📍 Location: Northtown Tavern & Pizza – 512 Allen St, Fredericktown, MO 63645
📝 Details:
- Bling Draw Tournament
- Casual and competitive players welcome
- 100% Payout
👉 Registration:
- Call to Pre-Register: (573) 944-8920
💲 Cost:
$20 entry fee
📅 Date: Saturday, May 2, 2026
🕕 Gates Open: 9:00 AM
🕕 Tractor Weigh-ins: 10:00 AM
🕕 Truck Weigh-ins: 2:00 PM
📍 Location: Pull Grounds – 400 Buford Blvd Fredericktown, MO 63645
📝 Details:
- Concessions and Beer Tent
- High-energy spectator event
💲 Cost:
- $10 general admission
- $20 Pit Passes
- Kids 12 & Under Free
📅 Date: Saturday, May 2, 2026
🕘 Registration: 9:00 AM – 12:00 PM
🕘 Judging: 12:00 PM – 2:30 PM
🕒 Awards: 3:00 PM
📍 Location: Court House Square, Fredericktown, MO – 1 Court Square, Fredericktown, MO 63645
📝 Details:
- Hosted by Foothills Car Club
- 25 vehicle classes with 3 trophies awarded per class
- Dash plaques for the first 100 registered vehicles
- 50/50 drawing and door prizes
- Special awards including Queen’s Choice, Mayor’s Choice, People’s Choice, Kid’s Choice, Ladies Choice, and Azalea Board Choice
- Multiple categories including original cars, street rods, street machines, motorcycles, trucks, and special interest vehicles
👉 Registration:
- Day-of registration available on-site between 9:00 AM – 12:00 PM
- Contact Bill Francis for more information: (573) 944-4781
💲 Cost:
- $20 entry fee per vehicle
🔥 Pro Tips for Competitors
✔ Register early for team sports (spots fill fast)
✔ Bring your own gear when applicable (basketball, paddle, etc.)
✔ Arrive early for check-in and warm-up
✔ Stay hydrated — it’s a full-day outdoor event
After a full lineup of events and competitions, one of the most exciting parts of the festival is exploring the vendor marketplace.
🛍️ Vendor Marketplace at the Festival
One of the biggest highlights of this year’s festival is the incredible lineup of local vendors, makers, small businesses, and community organizations. Whether you’re shopping for handmade goods, unique gifts, delicious treats, or supporting local causes, there’s something for everyone to explore.
👉 Tip: Be sure to walk the full vendor area — many booths feature one-of-a-kind items you won’t find anywhere else!
- Busy Bee Crochet
- Stitch & Giggles
- Crochet Blvd
- Heather’s Whimsical Creations
- Quilting Across the Creek
- Crafty Sisters Creations
- Sassy Stitches
- Lynn’s Creations
- Maria’s County Crafts
- Yawri Crafts
- Clyde’s Creations
- Magical Mothering
- Jersey Crafts
- At-T-tudes
- Hyjinx Prints LLC
* Featured Makers:
- EverJean Embroidery and More (custom embroidery & apparel)
- Holly’s Handcrafts (handmade goods & crafts)
- Mystic Sewing (sewing & textile creations)
- Creative Mom Custom Engraving (personalized engraved items)
- Layered Chaos (custom layered designs & crafts)
- T & B Woodworking
- Ron’s Woodcraft
- The Patriot Customs
- Fire Creek Customs
- T-Rex Customs
* Featured Vendors:
- The Farrier’s Wife Blacksmith Shop (hand-forged goods & demonstrations)
- The Creek Boutique (laser engraving, cutting boards, leather patch hats)
- Kelly Kelley
- Linda Wojtczuk
- Liberty Spices
- Heavenly Handbags
- Paparazzi Accessories
- Awesome Beaded Accessories
* Featured Shops:
- Whole Hearted (All Natural Crystal Jewelry)
- Charmingly Exquisite (unique jewelry pieces)
- Amy’s Stuff (accessories & boutique items)
- Candela Lucerna Natura (natural-inspired goods)
- Megan’s Scentsational Scents
- Lasting Scentsations
- Angie’s Pink Zebra
- Home Fragrance
Come hungry — these vendors are bringing the flavor:
- Thee Abbey Kitchen
- Flour Power
- Heavenly Creations and More Shop
* Must-Try Vendors:
- Jorya’s Baked Goods
- Oh, Fudge! Mackinac Fudge
- Papa K’s Seasoning
- Rooted & Refined (baked goods & artisan foods)
- SEMO 3D Prints
- Noodlemaker Prints
- Mack’s 3D Creations
- H3D Ticks Print Forge
Creative Highlights:
- Randy’s Creations and Duckiverse
- LinK Creations
- April’s MaD Kreations
- Kreations by Layton
- Groomer Has It
- Koda Buddies
- A Touch of Grace
- Dirty Lil Stack
- Wellness Choice
- The Station Craft Coffee & Bistro
- Walmart
- CC Restoration
- True Vine Restoration
- Uniquk Gifts and Handicrafts
These booths are a great way to connect with and support the community:
- Alcoholics Anonymous
- First Baptist Church
- East Missouri Action Agency
- Gideons International
- Madison County Democrats
- Missouri Bear Foundation
- Smallens Wild Bee Apiaries
- Fleer Enterprise
- Friends Deals
- Josie Reagan
- Alfred & Monica Coffey
- Jason DeGrant
- Valley Creations Co
- Ozarkmills
⚠️ Vendor Note (Important)
While every effort has been made to provide a complete and accurate list of vendors, vendor participation may vary slightly due to last-minute changes.
👉 Vendor list compiled from official festival materials and announcements. We recommend checking the official event page or visiting booths directly for the most up-to-date information.
🌸 Why the Fredericktown Azalea Festival Is a Must-Visit
The Fredericktown Azalea Festival is more than just an event—it’s a community tradition that brings the entire town to life, making it one of the top things to do in Southeast Missouri each spring.
It’s where:
- Families spend the entire day together, from morning events to evening entertainment
- Friends gather around live music, food vendors, and festival favorites
- Visitors experience the charm and hospitality of small-town Missouri firsthand
- The community comes together to celebrate spring in full bloom
With parades, competitions, local vendors, live entertainment, and activities happening all weekend long, there’s always something to see, do, or explore.
From supporting local businesses to reconnecting with neighbors and making new memories, the Azalea Festival is a perfect example of what makes Fredericktown—and Southeast Missouri—feel like home.
🏡 Curious What It’s Like to Live in Fredericktown?
Events like the Azalea Festival are just one example of what life in Fredericktown looks like year-round.
👉 If you’re exploring the area or thinking about making a move, start exploring:
📍 Plan Your Visit to Fredericktown
👉 Fredericktown Azalea Festival 2026
📅 May 1–3, 2026
📍 Fredericktown, Missouri
✔ Bring lawn chairs or blankets for live music and events
✔ Arrive early for fan-favorite activities (like the breakfast, 5K, and tournaments)
✔ Wear comfortable shoes — you’ll be walking between events, vendors, and the square
✔ Bring cash for vendors, food, and entry fees (some may not accept cards)
✔ Plan to stay all day — events, entertainment, and activities run throughout the weekend
💡 Pro Tip: Parking can fill up quickly near the square, so give yourself extra time to find a spot and explore the area.
For updates, schedules, and announcements, follow the official festival pages.
🌸 Experience Fredericktown in Full Bloom
If you’ve never been to the Azalea Festival, 2026 is the perfect year to go.
With the “Red, White, and Bloom” theme, expanded events, and a full lineup of music, vendors, and activities, this year’s festival is shaping up to be one of the best yet.
And if you’ve been before—you already know. There’s just something special about Fredericktown this time of year.
We’ll see you in Fredericktown. 🌸
❓ Fredericktown Azalea Festival 2026 FAQs
The Fredericktown Azalea Festival 2026 takes place Friday, May 1 through Sunday, May 3, 2026, with events scheduled throughout each day across downtown Fredericktown and Azalea Park.
Each day offers a different experience:
- Friday: Kickoff events and evening live music
- Saturday: The busiest day, featuring the 5K run, breakfast, tournaments, contests, vendor marketplace, and full-day entertainment
- Sunday: Community-focused events, including the Azalea Festival Parade at 2:00 PM, along with continued music and vendor activity
The festival is designed to be flexible, so visitors can attend for a few hours or spend the entire weekend exploring everything it has to offer.
For official tourism information about festivals and events in Missouri, you can visit: https://www.visitmo.com/events
Many parts of the Fredericktown Azalea Festival are completely free to attend, including:
- The parade
- Live music performances
- Vendor marketplace browsing
- Community activities and general admission areas
However, some events and competitions require entry fees or registration, such as:
- 5K Run & Walk ($10)
- Tournaments (basketball, pickleball, volleyball, golf, etc.)
- Car Show entry ($20 per vehicle)
- Specialty competitions like the Beer Stein Challenge
These fees typically support local organizations, scholarships, and community programs, making participation both fun and impactful.
For general guidance on how community events and festivals are structured and funded, you can reference: https://www.arts.gov (National Endowment for the Arts)
Fredericktown is a small city located in Madison County, Missouri, in the southeastern region of the state. It’s known for its strong sense of community, local events, and access to outdoor recreation, making it both a great place to visit and a desirable place to live.
The area offers:
- A close-knit, welcoming community
- Affordable housing compared to larger metro areas
- Access to parks, trails, and natural attractions
- Year-round local events like the Azalea Festival
For more detailed demographic, geographic, and economic information about Fredericktown, you can explore official data from the U.S. Census Bureau: https://www.census.gov
Additionally, Missouri’s official state resources provide helpful insights into the region and surrounding communities: https://www.mo.gov
🏡 Thinking About Calling Fredericktown Home?
Events like the Azalea Festival are just a glimpse into what makes Fredericktown, Missouri such a special place to live.
From strong community connections to year-round local events, it’s easy to see why so many people are searching for homes in Fredericktown MO and surrounding areas.
If you’ve spent time at events like the Azalea Festival, you already know how special this community is.
Whether you’re:
- Looking to buy your first home
- Searching for homes for sale in Fredericktown Missouri
- Exploring nearby communities in Southeast Missouri real estate markets
- Or thinking about selling your current property
👉 Our team is here to help you every step of the way.
We specialize in helping buyers and sellers navigate the Fredericktown real estate market with local insight, personalized guidance, and a focus on what matters most to you.
Whether you’re just visiting for the festival or considering a move, Fredericktown has something special to offer year-round.
🔑 Start Exploring:
- Browse homes for sale in Fredericktown MO
- Learn more about local neighborhoods and communities
- Connect with a local real estate expert for personalized support
- Get a personalized home value if you’re thinking about selling
👉 Ready to take the next step? Contact us today to get started—whether you’re just exploring or ready to make a move.
