Santa Rosa County’s Beaches to Woodlands tour is a chance to explore the area’s diverse culture and fall festivities! From bluegrass concerts, pumpkin patches and corn mazes to regattas, ziplines and sea turtles, there are fun events for people of all ages and interests throughout the season.

Here’s what’s currently on the schedule for the event’s 18th year of celebrating Santa Rosa!

Maps are available at the Visitor’s Center, or you can download and print your copy: Beaches to Woodlands 2021 map.

Event Dates and Descriptions

Sept. 3, 10, 17, 24, Oct. 1, 8, 15, 22 and 29

Bands on the Blackwater Fall Concert Series

5158 Willing St., Milton, FL. 7 to 9 p.m. Bands on the Blackwater is a free outdoor spring and fall concert series held Friday nights in downtown Milton. Pull up your boat or bring a lawn chair and relax while listening to great live music! For more information visit or call the City of Milton at 850-983-5400.

Sept. 3 – Nov. 6

Chain of Lakes Trail Self-Guided Interpretive Tour

Blackwater River State Park, 7720 Deaton Bridge Rd., Milton, FL. Come out on a nice fall day to enjoy the scenic route that is our chain of Lakes hiking trail. Approximately 1.5 mile in distance, this trail will traverse through many types of natural habitats supported by the park. On this self-guided tour, you will learn about the natural habitats as well as other very insightful facts about the park and trail. Parking is located in the “P” across from the Chain of Lakes trailhead. Park admission is $4 per vehicle. Please bring exact change and utilize the honor pay station located within the parking area. Grab a trail map on the boardwalk before embarking on your hike! For more information call the Ranger station at 850-983-5363 and to view the park map visit:

Sept. 4, 18, Oct. 2, 16, Nov. 6

Highway 87 Outdoor Market at Pik-itz

1922 Hwy 87, Navarre, FL. 9 a.m. to 1 p.m. This monthly outdoor market takes place on the first and third Saturday of each month. Farm to Table vendors are available along with arts & crafts and don’t miss out on shopping inside Pik-itz! For more information visit or call 850-710-7128.

Sept. 10, 11 and 12

31st Annual Juana Good Time Regatta

1451 Navarre Beach Causeway, Navarre Beach, FL. The Juana Good Time Regatta is designed for both experienced and novice racers, with the main emphasis being a “Good Time”. It is open to all sizes of multihull sailboats, from beach cats and trimarans to cruisers. For more information visit or call 850-939-1092.

Sept. 25


Ye Olde Brothers Brewery, 4458 Hwy 87, Navarre, FL. 11 a.m. to 5 p.m. The premier event of the year at Ye Olde Brothers Brewery! Come out and enjoy premium craft beer and authentic lagers in addition to traditional German fare and great music. For more information visit or call 850-684-1495.

Sept. 25 – Nov. 6

Holland Farms Pumpkin Patch & Maze

2055 Homer Holland Rd., Milton, FL. Sunday to Saturday 8 a.m. – 6 p.m. Enjoy a farm hayride that will take you around the farm and to the pumpkin patch to pick a pumpkin of your choice. New activities for this year include a ¾ mile train ride around the farm and a new innertube hill slide! Other activities include corn box, horse and regular swings, spider web, pirate ship, zip lines, pedal tractor cart racing, hill slides, rat racers, sand box and an 8-acre corn maze with kiddie maze. Every visitor receives a free cup of our famous homegrown boiled peanuts. Sit back and relax on our farm market porch, see you at the farm! Follow us on Facebook Holland Farms or Instagram: Hollandfarmsonline. For more information visit or contact BJ Holland at 850-675-6876 or email

Friday, Saturday, and Sunday nights in October

Whispering Pines Haunted Hayride & Zombie Shoot

1603 Penton Rd, Milton, FL. 7 p.m. to Midnight. Come out for some Spooktacular Fun! Halloween activities include Haunted Hayride, Zombie Bus Paintball Shoot, bonfire, live music, and concessions. For more information and admission prices visit or or call 850-304-1559.

Oct. 2 – Nov. 7

13th Annual Sweet Season Farms Corn Maze and U-Pick Pumpkins and Sunflowers

2260 Horn Rd., Milton, FL. Saturday 9 a.m. to 5 p.m., Sunday 11 a.m. to 5 p.m. Reserved school field trips only on weekdays. Visitors can spend time this fall season navigating their way through our fun and unique corn maze with plenty of room to spread out on the farm! U-pick sunflowers will be blooming in October along with our pumpkin patch. More details on our website and Facebook page. Over 25 fun farm themed activities, including our cow train, beeline zipline, corn popper jumping pillow, barnyard ball, farm themed playground and more! Plenty of food on site including the farm bakery with fresh squeezed lemonade, homemade caramel apples, roasted sweet corn, sno cones, kettle corn and much more! Find us on Facebook or Instagram for more details and event updates! For more information visit or call 850-686-9917 or email .

Oct. 2

1st Annual Challenge 22 Event Walk and Ride

Navarre Park, 8513 Navarre Parkway, Navarre, FL. 9 a.m. to 5 p.m. This event is sponsored by the American Legion Riders Chapter 382 to help bring awareness to the effects of Post-Traumatic Stress and the 22 veteran suicides a day. This community event will help raise money towards Project: VetRelief and feature an opening military ceremony, followed by a 2.2 mile walk and 22-mile motorcycle ride. There will be guest speakers, vendors, food, and live music throughout the day. You can register or donate at For more information, visit or call 850-420-4721.

Oct. 2

Juana’s Annual Oktoberfest Beer Tasting

Juana’s Pagodas & Sailor’s Grill, 1451 Navarre Beach Causeway, Navarre Beach, FL. 12 to 4 p.m. Festive atmosphere for adults to sample craft beers and food from the Sailor’s Grill along with activities for children staffed by the Navarre Beach Marine Science Station. For more information, visit or call 850-939-1092.

Oct. 2

Sea Turtle Extravaganza

Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL. 10 a.m. – 2 p.m. Shell-e-brate all things sea turtle through games, crafts, photo booth, costume characters, music and more! Free admission all day to the Navarre Beach Sea Turtle Conservation Center. NBSTCC is open until 4 p.m. For more information visit or call 850-684-3347.

Oct. 2
Take a Kid Fishing

8579 Gulf Blvd., Navarre Beach, FL. 8 a.m. This kid’s fishing clinic is staged at Navarre Beach Fishing Pier. First 200 children (12 and under) receive a fishing pole, goodie bag and includes free bait and fishing instruction. This event usually fills up quickly. Proceeds go to Navarre Chamber Foundation, a 501C3. For more information and to pre-register visit or

Oct. 2, 3

Navarre Fishing Rodeo

1451 Navarre Beach Causeway., Navarre Beach, FL. Tournament competition opens 12:01 a.m. Saturday – until 4 p.m. Sunday. Fish from the shore, a boat or kayak, or from the pier – you just can’t “fish” from the seafood market! Prizes will be awarded in all divisions. Weigh-in is on the beach at Juana’s, close to Santa Rosa County Boat Ramp and parking. Scales close promptly at 4 p.m. on both days. Up to two Junior anglers twelve and under can compete in the Junior Division for free with each paid rodeo admission. Proceeds from this event will benefit the Navarre Chamber Foundation which in turn benefits the Navarre Beach Marine Park. Visit our event website to find discounts from our local lodging partners for the week of the Navarre Fishing Rodeo. For more information visit or contact Sandi Kemp or Melinda Parnell at 850-939-1900 or email  

Oct. 9

87 Art Fest at Pik-itz

1922 Highway 87, Navarre, FL. 9 a.m. to 4 p.m. Kick off the shopping season with over 30 local artists, food trucks and live music. For more information, visit or call 850-710-1728.

Oct. 9

Fall Festival at the West Florida Railroad Museum

5003 Henry St., Milton, FL. 10 a.m. to 3 p.m. This event will include tours of the museum, historic presentations, model train displays, and the riding kids train and garden. Food vendors “Dadgum Good BBQ” and “Snowbiz Shaved Ice” will on site serving up delicious treats. For more information visit or

Oct. 9
13th Annual Run for the Reef 10K/5K and Kid’s One Mile Fun Run

8597 Gulf Blvd., Navarre Beach, FL. Run starts at 7:30 a.m. at the Navarre Beach boat launch parking lot. Features an out-and-back course along scenic Gulf Blvd. Event is a fundraiser to help “Make Navarre Snorkelicious,” a benefit for the Navarre Beach Marine Sanctuary and artificial reefs. Race Day Registration will be from 6 a.m. – 7 a.m. at Windjammers on the Pier. Awards will also be held at Windjammers on the Pier. For more information visit or contact Mike Sandler at 850-686-6643 or email

Oct. 9
20th Annual Navarre Car, Truck, and Bike Show and Craft Fair

Navarre High School, 8600 High School Blvd., Navarre, FL. 8 a.m. to 4 p.m. More than 100 historical cars from all decades are on display in this popular event. Event features music, food, vendor booths and a craft fair. For more information, visit or call 850-501-2244.

Oct. 9

Bluegrass in the Woods

Sunburst RV Resort, 2375 Horn Rd., Milton, FL. 7 – 9 p.m. This free event will feature bluegrass music, s’mores around the fire pit and plenty of toe tapping. Bring your own lawn chairs and enjoy the peaceful setting. RV sites, cabins, and tent sites can be rented to make a weekend of it. For more information visit or call 850-675-6807.

Oct. 9, 16, 23, 30

Spooky Shark School

Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL. 9 to 10 a.m. Explore sharks of the deep when the Navarre Beach Sea Turtle Conservation Center Shark School goes Spooky in October. Explore local gulf coast sharks, shark biology, and shark conservation. Shark school participates receive: Introduction class to sharks of the Gulf of Mexico, shark arts and crafts, shark tooth treasure hunt, a certificate of completion, and early entrance to the NBSTCC. For more information and to register, visit or call 850-684-3347.

Oct. 10

Annual Charity Chili Cook-off and Volleyball Tourney

Juana’s Pagodas & Sailor’s Grill, 1451 Navarre Beach Cswy., Navarre Beach, FL. 10 a.m. to 4 p.m. Event is a fundraiser for Caring and Sharing of South Santa Rosa County. Fee required to enter the chili cookoff or the volleyball tournament. Donation fee required to taste. Bring already cooked and hot chili in crock pots with serving ladles to set up between noon and 2 p.m.; chili tastings take place from 2 to 4 p.m. Volleyball registration at 10 a.m. and tournament starts at 10:30 a.m. Four-person co-ed teams any skill levels, will be paired according to skill level. For more information visit or call 850-939-1092.

Oct. 15, 16

Spirits of the Simpson House Tour

Arcadia Homestead Site, 4755 Anna Simpson Rd., Milton, FL. Join us for a spooky evening of history and hauntings at the restored Simpson House Museum that highlights the life at Arcadia Farms during the Great Depression. The multi-sensory exhibit features a mixture of staged, historic furniture and interactive exhibits. This event requires pre-purchased tickets, limited spots available for each tour. For more information and tickets visit

Oct. 16

Pink Pirate’s Save Second Base Annual 5K Run

8578 Gulf Blvd., Navarre Beach, FL. 8 a.m. Breast Cancer Awareness Run. Race starts at the Navarre Beach boat ramp parking lot. Pink Pirates is a 501C non-profit organization dedicated to raising awareness and funds to assist with early detection of breast cancer. For more information visit or call 850-323-8287 or email

Oct. 16, 17, 23, 24, 30 and 31

Boo at the Zoo – Trick or Treat Trail

Gulf Breeze Zoo, 5701 Gulf Breeze Pkwy., Gulf Breeze, FL. 10 a.m. to 5 p.m. Trick-or-Treat with all your favorite animals! Boo at the Zoo offers 6 days of scare-free, daytime fun for children and their families. Join our safe zoo neighborhood of Halloween entertainment, with kid-friendly fun around every corner. Includes trick-or-treat trail with toys, treats, treasures, bounce houses, face painting, animal ambassador headquarters and the entire zoo! Save time and purchase your tickets online! For more information visit or call 850-932-2229.

Oct. 22, 23

1st Annual Batty Halloween Wing-Ding!

Emerald Coast Wildlife Refuge, 3051 Cloptons Cir., Navarre, FL. Friday 5 to 8 p.m. and Saturday 4 to 8 p.m. Join us and our animal ambassadors for games, crafts, and candy. Let Rose the Raccoon teach you how to play ring toss the right way or get your picture taken at the hissing booth with Butch the Corn Snake. Take a walk through our kid friendly haunted trail and take a flying lesion from Aries the Red-Shouldered Hawk. Dress up in your favorite Halloween costume! Admission fee required, discount for visitors in Halloween costumes. For more information visit or call 850-684-1485.

Oct. 23
Science Spooktacular by the Sea presented by the Navarre Beach Marine Science Station

8638 Blue Heron Ct., Navarre Beach, FL. 5 p.m. to 9 p.m. From creeps of the deep, an endangered species cemetery, to science that glows in the dark, amazing sea creatures await you. Join us for our annual fundraiser Science Spooktacular. Explore science stations led by outstanding Santa Rosa County teachers. The family friendly event features glow in the dark science demonstrations, spine chilling dissections, haunted beach walk, hands-on activities, and crafts for children. For more information and pricing visit or call 850-261-2141.

Oct. 29, 30
Annual Ghost Walk Downtown Milton

 6866 Caroline Street, Milton, FL. Tours will begin at the Imogene Theatre in Milton starting at 6 p.m. each evening. Tours will leave approximately every 25 minutes until around 10 p.m. Tours last 30 to 45 minutes. Event website:

Oct. 30
Annual Fenner McConnell/Mark Wantz Blackwater Heritage Century Ride

Milton Community Center, 5629 Byrom St., Milton, FL. Ride starts at 7:30 a.m. Mark your calendars for a spooky Fenner Ride 2021! October is a great time to get outside, enjoy the cooler temperatures, reconnect with nature, and enjoy all that life has to offer. Big Brothers Big Sisters of Northwest Florida and the West Florida Wheelmen Bicycle Club host this great event. This ride gives a unique chance to experience Northwest Florida’s native wildlife, natural environments, and beautiful scenery. A ride for all cycling levels, you choose 18, 42, 62, or 100 miles.Registration includes event giveaways, fully supported rest stops, limited sag support, a post-ride meal, great prize opportunities, a t-shirt, and medals for all participants. For more information and to register visit

Oct. 30

Halloween, Hallow-Seas Saturday

Navarre Beach Sea Turtle Conservation Center, 8740 Gulf Blvd., Navarre Beach, FL. 10 a.m. to 2 p.m. Celebrate Halloween in the Seas with free activities and upcycled arts and crafts outside the Navarre Beach Sea Turtle Conservation Center, story time with “Duffy’s Lucky Escape”, photo booth fun and a Turtle Excluder Device display. Take a tour of the Conservation Center to learn about Sweet Pea’s Journey along with many other animal exhibits. The NBSTCC will be open to 4 p.m. with general admission fees. For more information visit or call 850-684-3347.

Oct. 30

Trash Bash with the Navarre Beach Sea Turtle Conservation Center

8649 Gulf Blvd., Navarre Beach, FL. 8 to 10 a.m. Halloween themed for the month of October. Guests are encouraged to wear costumes that are upcycled and/or marine themed! Help protect sea turtles and other imperiled species through a citizen science program that allows volunteers to take an active role in the war against marine debris. Volunteers collect trash from different areas along the 4.5 miles of Navarre Beach and record data that is forwarded to state and federal agencies. Meet in the main Navarre Beach Parking Lot near the Sand Crab Pavilion. A limited supplies of gloves, buckets and pickers are provided, or bring your own. For more information, visit or call 850-684-3347.

September – October – November: All Month Long

Adventures Unlimited Fall Foliage Zipline Tours

8974 Tomahawk Landing Rd., Milton, FL. Fall is a great time to enjoy the many natural attractions at Adventures Unlimited located just north of Milton, FL., in the Blackwater River State Forest. Enjoy the changing colors and the rush of excitement while doing one of the Canopy Zipline Tours. Overnight accommodations at the resort’s camp sites or cabins are available along with canoeing and kayaking down the majestic Coldwater Creek. Inquire about team building activities and group outings also. For more information visit or call (850) 623-6197.

Holley Hill Pottery and Art Studio Kiln Openings

7507 Buckeye Dr., Navarre, FL. 10 a.m. to 4 p.m. Open Tuesday to Saturday on the Tour! Holley Hill Pottery has been making pottery in Santa Rosa County for over 40 years capturing the lifestyle, scenery and sea life of the Gulf Coast using local clays and their own glaze formulas. For more information visit or call 850-939-2744 or email

Gulf Coast Kiln Walk Society

7507 Buckeye Dr., Navarre, FL. 10 a.m. to 4 p.m. Kilns can be toured every Saturday on the Tour. Kiln Walkhas the largest historical 32-foot wood fueled “Anagama” cave style kiln and the only reconstructed wood fueled Southern Altered Groundhog kiln from the 1940s in the State of Florida. Both historical kilns are available to view on the tour. For more information visit or call 850-939-2744 or email