Beaches To Woodlands Unleashes a Medley of Fall Festivities

As fall approaches, the scenic coastal wonder of Navarre Beach welcomes a magnificent transition into the season. Nestled in Santa Rosa County, the Beaches To Woodlands festival unveils a diverse array of events and activities designed to showcase the vibrant spirit of the season. From art and music festivals to family-friendly adventures and Halloween-themed fun, Beaches To Woodlands promises an unforgettable experience for all visitors.

This is the 20th year of Beaches To Woodlands, showcasing the very best of fall events in Santa Rosa County. Since its inception, the celebration has grown immensely, with events spanning throughout September, October, and November, making it a comprehensive autumn extravaganza! The festival embraces a wide variety of events to cater to every interest, from art enthusiasts and music aficionados to nature lovers and families seeking quality time together. Whether you’re in the mood for artistic fun, thrilling outdoor escapades, or simply immersing yourself in the seasonal charm, Beaches To Woodlands has it all.

Beaches To Woodlands Signature Events

Bands on the Blackwater Fall Concert Series
(Sept. – Oct. | Fridays, 7 – 9 pm)

Unwind on Friday nights in historic downtown Milton as you groove to the beats of live music by the Blackwater River. This year’s lineup includes The Flavors, Casey Kearney, Whitesands Panhandle Band, Karli Ryan, The Six Piece Suits, The Midnight Shepherds, Jarred McConnell & the High Aces, Nobius, and The Modern Eldorados. This free outdoor concert series is perfect for a relaxing evening, whether you choose to listen from the banks or bring your boat for a unique concert experience on the water.

33rd Annual Juana Good Time Regatta
(Sept. 8, 9, 10)

The Juana Good Time Regatta promises an exhilarating experience for both seasoned sailors and newcomers, with its primary focus on having an absolute blast! This event is open to all sizes of multihull sailboats, including beach cats, trimarans, and cruisers, ensuring a diverse and exciting competition on the water.

Spanning three exciting days from September 8th to 10th, the Regatta is a celebration of sailing, camaraderie, and fun. Participants and spectators alike can look forward to lively parties, delectable food offerings, and the vibrant rhythms of live music, creating an electric atmosphere throughout the event.

The festivities kick off with The Wish for Wind Party on September 8th, from 6 to 8 pm, where participants can pick up their race packets and revel in the excitement building up for the upcoming sailboat races. Speaking of the races, they take place on Saturday and Sunday, from 11 am to 3 or 4 pm, depending on the whims of the wind, adding an element of unpredictability to the competition.

Whether you’re a seasoned sailor eager for the thrill of the race or a curious newcomer seeking to soak in the energy of the event, the Juana Good Time Regatta promises an unforgettable experience on the picturesque waters of Navarre Beach.

Navarre Fishing Rodeo
(Oct. 7 and 8)

Prepare your fishing gear and get ready for the Navarre Fishing Rodeo, an exciting fishing extravaganza that welcomes anglers of all ages and skill levels! This event offers a wide array of fishing opportunities, allowing participants to cast their lines from the shore, a boat, a kayak, or the pier, ensuring a thrilling and diverse fishing experience.

As you reel in your catches, anticipation builds for the prize awards in all divisions, recognizing outstanding catches and showcasing the best of the fishing prowess among the participants. The weigh-in takes place on the beach at Juana’s, conveniently located close to the Santa Rosa County Boat Ramp and parking, making it easy to showcase your trophy catches.

For the young fishing enthusiasts, the Navarre Fishing Rodeo is especially inclusive, allowing up to two Junior anglers, aged twelve and under, to compete in the Junior Division absolutely free with each paid rodeo admission. This gesture aims to foster a love for fishing among the next generation and encourages family participation in this wonderful event.

Apart from the joy of fishing and the thrill of competition, the Navarre Fishing Rodeo holds a noble cause at its heart. Proceeds from this event go towards supporting the Navarre Chamber Foundation, which, in turn, benefits the Navarre Beach Marine Park, contributing to the conservation and preservation of this cherished marine ecosystem.

15th Annual Sweet Season Farms Corn Maze and U-Pick Pumpkins and Sunflowers
(Sept. 30 – Nov. 5 | Sat., 9 am – 5 pm, Sun., 11 am – 5 pm)

Get ready for an exhilarating adventure that promises to challenge and delight you – it’s time to conquer the Sweet Season Farms corn maze. Gather your family and friends and embark on an unforgettable journey through our legendary corn maze. Each year, Sweet Season Farms crafts a brand-new design, ensuring that the maze is a fresh and exciting experience for all. From humble beginnings of 5 acres, their maze has flourished into a sprawling 8-acre labyrinth of twists and turns, nestled in the heart of an expansive 10-acre corn and sunflower field. With so much space to explore, get ready to truly lose yourself in the thrilling maze adventure.

The joy of autumn harvest is highlighted with a fantastic pumpkin-picking experience. As you wander through the vibrant pumpkin patch, you’ll find an array of pumpkins available for purchase, with prices varying based on their size. Whether you’re searching for a petite pumpkin to adorn your doorstep or a grand one to carve into a spooky masterpiece, they have just the perfect one for you. To make your pumpkin-picking experience even more enjoyable, convenient pumpkin wagons are available exclusively for carrying your prized pumpkin haul.

List of All Beaches To Woodlands Events

The diverse array of events at Beaches To Woodlands offers something for everyone. Here’s a list of all the exciting happenings during the festival:

Adventures Unlimited Fall Foliage Zipline Tours

    • Date: Sept. – Nov.
    • Location: 8974 Tomahawk Landing Rd., Milton, FL

Bands on the Blackwater Fall Concert Series

    • Date: Sept. – Oct. | Fridays, 7 – 9 pm
    • Location: 5158 Willing St., Milton, FL
    • Concert Dates:

Highway 87 Outdoor Market at Pik-itz

    • Dates: Sept. 2, 16, Oct. 7, 21, Nov. 4 | 9 am – 1 pm
    • Location: 1922 Hwy 87, Navarre, FL

33rd Annual Juana Good Time Regatta

    • Dates: Sept. 8, 9, and 10
    • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

Navarre Beach Art, Beer & Wine Festival

    • Date: Sept. 10 | 10 am – 7 pm
    • Location: 8649 Gulf Blvd., Navarre Beach, FL

September 11th Memorial Stair Climb

    • Date: Sept. 11 | 7 am – 12 pm
    • Location: 8573 Gulf Blvd, Navarre Beach, FL

Oktoberfest at Ye Olde Brothers Brewery

    • Date: Sept. 23 | 11 am – 4 pm
    • Location: 4458 Hwy 87, Navarre, FL

Holland Farms Pumpkin Patch & Maze

    • Date: Sept. 23 – Nov. 4 | Sun. to Sat., 8 am – 6 pm
    • Location: 2055 Homer Holland Rd., Milton, FL

3rd Annual Challenge 22 Event Walk and Ride

    • Date: Sept. 30 | 9 am – 4 pm
    • Location: 8513 Navarre Parkway, Navarre, FL

15th Annual Sweet Season Farms Corn Maze and U-Pick Pumpkins and Sunflowers

    • Date: Sept. 30 – Nov. 5th | Sat., 9 am – 5 pm, Sun., 11 am – 5 pm*
    • Location: 2260 Horn Rd., Milton, FL

Navarre Fishing Rodeo

    • Dates: Oct. 7 & 8
    • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

St. Michael’s Brewing Co. 3rd Anniversary Bash

    • Date: Oct. 7 | 6:30 pm
    • Location: 2199 Hwy. 87, Navarre, FL

Juana’s Annual Oktoberfest Beer Fest

    • Date: Oct. 7 | 12 – 4 pm
    • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

Take a Kid Fishing

    • Date: Oct. 7 | 8 am
    • Location: Navarre Beach Fishing Pier, 8579 Gulf Blvd., Navarre Beach, FL

Spooky Shark School

    • Dates: Oct. 7, 14, 21 | 9 – 10 am
    • Location: 8740 Gulf Blvd., Navarre Beach, FL

Fall Festival at the West Florida Railroad Museum

    • Date: Oct. 7 | 10 am – 3 pm
    • Location: 5003 Henry St., Milton, FL

Sea Turtle Extravaganza

    • Date: Oct. 8 | 10 am – 2 pm
    • Location: Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL

Bluegrass in the Woods

    • Date: Oct 14 | 7 – 9 pm
    • Location: Sunburst RV Resort, 2375 Horn Rd., Milton, FL

Navarre Beach Autorama Friday Night Cruise-In Presented by Pirates on the Panhandle

    • Date: Oct 13 | 6 pm
    • Location: 8649 Gulf Blvd, Navarre, FL

22nd Annual Navarre Beach Autorama: Car, Truck, and Bike Show

    • Date: Oct. 14 | 8 am – 4 pm
    • Location: Navarre High School, 8600 High School Blvd., Navarre, FL

15th Annual Run for the Reef 10K/5K and Kids One Mile Fun Run

    • Date: Oct. 14 | 6 am
    • Location: 8597 Gulf Blvd., Navarre Beach, FL

Munson Heritage Festival

    • Dates: Oct. 14 and 15 | 9 am – 5 pm
    • Location: Krul Lake Recreation Area, Milton, FL

Annual Charity Chili Cook-off and Volleyball Tourney

    • Date: Oct. 15 | 10 am – 4 pm
    • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

Pink Pirates Get It Off Your Chest Annual 5K Run

    • Date: Oct. 21 | 8 am
    • Location: 8578 Gulf Blvd., Navarre Beach, FL

Boo at the Zoo – Trick or Treat Trail

    • Dates: Oct. 14-15, 21–22, 28–29 | 10 am – 5 pm
    • Location: 5701 Gulf Breeze Pkwy., Gulf Breeze, FL

Annual Ghost Walk Downtown Milton

    • Dates: Oct. 2 & 21 | 6 pm
    • Location: 6866 Caroline Street, Milton, FL

3rd Annual Batty Fang-Tastic Halloween

    • Date: Oct. 21 | 3 – 7 pm
    • Location: Emerald Coast Wildlife Refuge, 3051 Cloptons Circle, Navarre, FL

Science Spooktacular by the Sea presented by the Navarre Beach Marine Science Station

    • Date: Oct. 21 | 5 pm – 9 pm
    • Location: 8638 Blue Heron Ct., Navarre Beach, FL

Annual Fenner McConnell/Mark Wantz Blackwater Heritage Trail Ride

    • Date: Oct. 28 | 7:30 am
    • Location: 5629 Byrom St., Downtown Milton

Trash Bash with the Navarre Beach Sea Turtle Conservation Center

    • Date: Oct. 28 | 8 – 10 am
    • Location: 8649 Gulf Blvd., Navarre Beach, FL

Holley Hill Pottery and Art Studio Kiln Openings

    • Date: Tues. – Sat, 10 am – 4 pm
    • Location: 7507 Buckeye Dr., Navarre, FL

Gulf Coast Kiln Walk Society

    • Date: Saturdays, 10 am – 4 pm
    • Location: 7507 Buckeye Dr., Navarre, FL