Beaches to Woodlands Unleashes a Medley of Fall Festivities

 

As fall approaches, Santa Rosa County comes alive with the 21st annual Beaches to Woodlands event series, a beloved celebration of the season running from September through early November. This year, the festival promises to deliver a spectacular lineup of family-friendly activities, from the charming Bands on the Blackwater Fall Concert Series to the exciting Navarre Fishing Rodeo and the ever-popular Sweet Season Farms Corn Maze.

With over two decades of tradition, Beaches to Woodlands continues to enchant both locals and visitors alike with its diverse array of festivities, ensuring there’s something for everyone to enjoy. Whether you’re looking to celebrate Halloween or Oktoberfest or simply want to enjoy the best of the season, join us for an unforgettable experience. Discover the magic of fall with a community that truly knows how to celebrate in style!

Beaches to Woodlands Signature Events

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

Unwind on Friday nights in historic downtown Milton with Bands on the Blackwater, a free outdoor concert series perfect for the whole family! This year’s lineup includes Disco Kiss, Six Piece Suits, Chase Mitchell, Doc Johnson Band, Bad Juju, The New Cahoots, 3 day Weekend, Horseshoe Kitty, and Ben Loftin & the Family. With great live music and rotating food trucks offering delicious dinner options, it’s the ideal way to spend a relaxing evening. Whether you choose to listen from the riverbanks or experience the concert on the water, you’re guaranteed to have an unforgettable time.

Stay in the loop with food truck lineups, weather updates, and all the latest buzz from Bands on the Blackwater by following their Facebook page.

34th Annual Juana Good Time Regatta
(Sept. 6 – 8)

The Juana Good Time Regatta promises a fantastic time on the water for both seasoned sailors and newcomers. Open to all sizes of multihull sailboats— from beach cats and trimarans to cruisers—this event takes place from September 6th to 8^th. Enjoy lively parties, delectable food, and vibrant live music, creating an electric atmosphere for participants and spectators alike.

Every participant gets a commemorative t-shirt (while supplies last) and access to multiple parties featuring complimentary and discounted food and drinks all weekend long. Plus, experienced sailors without a boat can join the thrilling Hobie Wave timed beach races using Key Sailing’s rental boats.

The festivities kick off with The Wish for Wind Party on September 6th, from 6 to 8 p.m. Participants can pick up their race packets and enjoy a complimentary draft, light munchies, and $4 Blue Chair Bay Rum provided by Sailors Grill and Juana’s Pagodas. Live music will be featured in multiple locations, including the Deck and the Beach Stage, with performances by Drop Dead Dangerous, Stevie Hall, and Horseshoe Kitty.

On Saturday, September 7th, the races finally begin! Start your day with a continental breakfast provided by Sailors’ Grill, followed by a Skippers’ Meeting on the Beach Stage. The day’s races, including distance and timed Hobie Wave races, will commence based on the weather conditions discussed at the meeting. They typically run from around 11 am to 3 or 4 p.m., both Saturday and Sunday. Enjoy live music throughout the day and a Sailors’ Buffet in the evening with free draft, food, and drink specials.

Sunday, September 8^th—the event’s final day—begins with another continental breakfast followed by a Skippers’ Meeting on the Beach Stage. Buoy/Triangle races and timed Hobie Wave races will take place, culminating in an awards party with party subs, drink specials, a racing slide show, and live music. Handcrafted trophies by Holley Hill Pottery will be awarded to the winners.

Navarre Fishing Rodeo
(Oct. 5 and 6)

Gear up for an unforgettable fishing experience at the Navarre Fishing Rodeo! This exciting competition, perfect for anglers of all ages and skill levels, runs from Saturday, October 5th to Sunday, October 6th. Cast your line from the shore, a boat, a kayak, or the pier—just not from the seafood market! With a wide variety of fishing options, there’s something for everyone to enjoy.

The event kicks off with a Captain’s Meeting on Friday, October 4th, where participants can pick up their Captain’s bags and t-shirts. Then, the competition officially begins on Saturday, with weigh-ins held from 1-4 p.m. each day at Juana’s on the beach, conveniently located near the Santa Rosa County Boat Ramp. Ensure your catches are in by 4 p.m. each day, as scales close promptly.

Young anglers aged twelve and under can fish for free in the Junior Division with paid adult admission, fostering a love for the sport in the next generation. Proceeds from the rodeo support the Navarre Chamber Foundation, benefiting the Navarre Beach Marine Park and contributing to conserving our beautiful marine environment.

At the Navarre Fishing Rodeo, anglers can compete for impressive cash prizes awarded to the heaviest fish in each eligible species category, with $125 for First Place, $75 for Second Place, and $25 for Third Place. Additionally, the coveted SLAM category offers a grand prize of $250 for the highest total weight, making the competition even more thrilling. Junior anglers also have a chance to shine with cash prizes of $200 for First Place and $100 for Second Place, based on their total catches over both days.

Don’t miss out on this thrilling and community-driven event! Visit the event website to find discounts from our local lodging partners for the week of the Navarre Fishing Rodeo. For more info, visit navarrefishingrodeo.com or follow their Facebook page.

16th Annual Sweet Season Farms Corn Maze and U-Pick Pumpkins and Sunflowers
(Sept. 28 – Nov. 3 | Sat., 9 a.m. – 5 p.m., Sun., 11 a.m. – 5 p.m.)

Gather your family and friends and get ready to take on Sweet Season Farms’ legendary corn maze. Each year, this family-owned farm unveils a brand-new design, ensuring you’ll never have the same experience twice. Although the corn maze originally began as 5 acres, it’s now expanded into a sprawling 8-acre labyrinth of twists and turns. With so much space to explore, get ready to truly lose yourself in the thrilling maze adventure.

Beyond the corn maze, there’s so much more to see! Sweet Season Farms features over 25 fun, farm-themed activities, including a cow train, beeline zipline, corn popper jumping pillow, barnyard ball, playground, and more. Plus, you’ll find all sorts of delicious food around the farm. For example, the bakery offers fresh-squeezed lemonade, homemade caramel apples, roasted sweet corn, sno-cones, and kettle corn, among other fun fall treats!

Of course, why not pick out a pumpkin while you’re here? 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. To make your pumpkin-picking experience even more enjoyable, the farm even provides pumpkin wagons to help carry around the pumpkins of your choice.

A percentage of all Pink Pumpkin sales go to the American Cancer Society, so your purchase helps support a great cause. And don’t forget, U-pick sunflowers will be blooming in October, too, adding a whole other reason to visit!

 

List of All Beaches to Woodlands Events

The Beaches to Woodlands offers something fun for everyone, whether you’re a couple looking to listen to live music, an experienced angler, or a parent seeking an exciting way to celebrate fall with the kids. Here’s a list of all the seasonal happenings during the festival that you won’t want to miss:

Adventures Unlimited Fall Foliage Zipline Tours

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

Bands on the Blackwater Fall Concert Series

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

1. • • Aug 30 – Disco Kiss
     • Sept 6 – Six Piece Suits
     • Sept 13 – Chase Mitchell
     • Sept 20 – Doc Johnson Band
     • Sept 27 – Bad Juju
     • Oct 4 – The New Cahoots
     • Oct 11 – 3 day Weekend
     • Oct 18 – Horseshoe Kitty
     • Oct 25 – Ben Loftin & the Family

Highway 87 Outdoor Market at Pik-itz

1. • Dates: Sept. 7, 21, Oct. 5, 19, Nov. 2 | 9 a.m. – 1 p.m.
   • Location: 1922 Hwy 87, Navarre, FL

Sand Dollar Saturdays

1. • Dates: Saturdays, Spet. – Nov. | 9 am – 1 pm
   • Location: 1900 Hwy. 87., Navarre, FL

34th Annual Juana Good Time Regatta

1. • Dates: Sept. 6 – 8
   • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

September 11th Memorial Stair Climb

1. • Date: Sept. 11 | 7 a.m. – 12 p.m.
   • Location: 8573 Gulf Blvd, Navarre Beach, FL

Oktoberfest at Ye Olde Brothers Brewery

1. • Date: Sept. 25 – 29 | 11 a.m. – 7 p.m.
   • Location: 4458 Hwy 87, Navarre, FL

Holland Farms Pumpkin Patch & Maze

1. • Date: Sept. 21 – Nov. 3 | Sun. to Sat., 8 a.m. – 6 p.m.
   • Location: 2055 Homer Holland Rd., Milton, FL

16th Annual Sweet Season Farms Corn Maze and U-Pick Pumpkins and Sunflowers

1. • Date: Sept. 28 – Nov. 3 | Sat., 9 a.m. – 5 p.m., Sun., 11 a.m. – 5 p.m.
   • Location: 2260 Horn Rd., Milton, FL

Christ Methodist of Milton’s Annual Pumpkin Patch and Hayrides

1. • Date: Throughout October | 11 a.m. – 7 p.m.
   • Location: 5983 Dogwood Dr., Milton, FL

Navarre Fishing Rodeo

1. • Dates: Oct. 5 & 6 | Tournament opens at 12:01 a.m. Sat. and closes at 4 p.m. Sun.
   • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

St. Michael’s Brewing Co. 4th Anniversary Bash

1. • Date: Oct. 12 & 13 | 11 a.m. – 7 p.m.
   • Location: 2199 Hwy. 87, Navarre, FL

Juana’s Annual Oktoberfest Beer Fest

1. • Date: Oct. 5 | 12 – 4 p.m.
   • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

Take a Kid Fishing

1. • Date: Oct. 5 | 8:30 a.m.
   • Location: Navarre Beach Fishing Pier, 8579 Gulf Blvd., Navarre Beach, FL

Depot Day at the West Florida Railroad Museum

1. • Date: Oct. 5 | 10 a.m. – 3 p.m.
   • Location: 5003 Henry St., Milton, FL

Sea Turtle Extravaganza

1. • Date: Oct. 12 | 10 a.m. – 2 p.m.
   • Location: Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL

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

1. • Date: Oct 11 | 6 p.m.
   • Location: 8649 Gulf Blvd, Navarre, FL

24th Annual Navarre Beach Autorama: Car, Truck, and Bike Show

1. • Date: Oct. 12 | 8 a.m. – 4 p.m.
   • Location: Navarre High School, 8600 High School Blvd., Navarre, FL

16th Annual Run for the Reef 10K/5K and Kids One Mile Fun Run

1. • Date: Oct. 12 | 6 a.m.
   • Location: 8597 Gulf Blvd., Navarre Beach, FL

Munson Heritage Festival

1. • Dates: Oct. 12 and 13 | 9 a.m. – 5 p.m.
   • Location: Krul Lake Recreation Area, Milton, FL

Boo at the Zoo – Trick or Treat Trail

1. • Dates: Oct. 12-13, 19–20, 26–27 | 10 a.m. – 5 p.m.
   • Location: 5701 Gulf Breeze Pkwy., Gulf Breeze, FL

Annual Charity Chili Cook-off and Volleyball Tourney

1. • Date: Oct. 13 | 10 a.m. – 4 p.m.
   • Location: 1451 Navarre Beach Causeway, Navarre Beach, FL

Pink Pirates Get It Off Your Chest Annual 5K Run

1. • Date: Oct. 19 | 8 a.m.
   • Location: 8578 Gulf Blvd., Navarre Beach, FL

The Starfish Project’s Wing Cook-Off

1. • Date: Oct. 19 | 11:30 a.m. – 4 p.m.
   • Location: Navarre Park, 8513 Navarre Pkwy., Navarre, FL

4th Annual Batty Fang-Tastic Halloween

• • Date: Oct. 19 | 3 – 7 p.m.
  • Location: Emerald Coast Wildlife Refuge, 3051 Cloptons Circle, Navarre, FL

Spooky Shark School

• • • Date: Oct. 26 | 8:30 a.m. – 10 a.m.
    • Location: Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL

Annual Fenner McConnell/Mark Wantz Blackwater Heritage Trail Ride

1. • Date: Oct. 26 | 7:30 a.m.
   • Location: 5629 Byrom St., Downtown Milton

Monarch Madness

1. • Date: Oct. 26 | 9 a.m. – 1 p.m.
   • Location: 4966 Henry St., Milton, FL

Trash Bash with the Navarre Beach Sea Turtle Conservation Center

1. • Date: Oct. 26 | 8 – 10 a.m.
   • Location: 8649 Gulf Blvd., Navarre Beach, FL

Holley Hill Pottery and Art Studio Kiln Openings

1. • Date: Tues. – Sat, 10 a.m. – 4 p.m.
   • Location: 7507 Buckeye Dr., Navarre, FL

Gulf Coast Kiln Walk Society

1. • Date: Saturdays, 10 a.m. – 4 p.m.
   • Location: 7507 Buckeye Dr., Navarre, FL