Winter Garden & Oakland: Central Florida’s Most Bikeable Escape
🎧 Winter Garden & Oakland: Central Florida’s Most Bikeable Escape
What happens when two small towns decide not to become suburbs?
That’s the story at the heart of this episode, an exploration of Winter Garden and Oakland, Florida. Just west of Orlando, these two connected communities have done what so many others have failed to do: preserve their history and authenticity while quietly becoming two of the most desirable places to visit (or live) in Central Florida.
In this podcast, we slow things down and take a deep look at the people, places, and planning that make Winter Garden and Oakland stand out. This isn’t a theme park story. It’s a story about intention, design, and a shared vision for livability.
🏙️ A Downtown That Got It Right
Winter Garden’s historic downtown has become a model for small-town revitalization across Florida.
Historic District: Once a fading citrus town, Winter Garden reinvented itself through smart preservation and streetscape planning. The brick streets, bike-friendly layout, and adaptive reuse of old buildings now define its charm.
Edgewater Hotel (99 W Plant St) — A restored 1920s hotel that now serves as both a boutique inn and a living museum of Florida hospitality.
historicedgewater.com
Adjectives Market (131 W Plant St) — A sprawling vintage and artisan marketplace perfect for home décor hunters and curious browsers.
shopadjectives.com
Ruby & Rust (49 S Main St) — Locally loved for its eclectic gifts, antiques, and modern Southern aesthetic.
rubyandrust.com
🎧 Listen for a reflection on how Winter Garden preserved authenticity without becoming artificial, a delicate balance few towns achieve.
☕ Cafés, Trails, and Everyday Life
What makes Winter Garden so livable isn’t just its shops, it’s the rhythm of daily life.
Axum Coffee (146 W Plant St) and Rosallie Le French Café (141 W Plant St) — Morning staples with strong local followings.
Crooked Can Brewing Company & Plant Street Market (426 W Plant St) — A communal hub blending craft beer, food stalls, and live music.
crookedcan.com
West Orange Trail — The 22-mile paved trail linking Winter Garden to Oakland and Apopka. Bike it, walk it, or just people-watch. It’s the social spine of the community.
Newton Park (31 W Garden Ave) — Overlooking Lake Apopka, this serene green space connects the town’s present to its natural roots.
💡 Pro tip: Rent a bike downtown and explore the trail’s shaded route toward Oakland—Florida’s most scenic suburban ride.
🌳 Oakland: The Town That Chose Stillness
If Winter Garden is the heartbeat, Oakland is the pause that gives it meaning.
Prairie House Coffee Co. (4 N Tubb St) — The town’s unofficial living room, serving espresso and small-town conversation.
prairiehousecoffee.com
Oakley’s Trailside Treats — A family-friendly ice cream stop along the West Orange Trail.
Oakland Manor House (620 N Tubb St) — A historic home turned inn, offering a quiet retreat surrounded by oak canopies.
Oakland Nature Preserve (747 Machete Trail) — 128 acres of protected land along Lake Apopka with boardwalks, trails, and education centers focusing on restoration and wildlife.
🌾 Oakland’s approach is slower, quieter, and fiercely intentional, a town that prizes green space over growth.
🧺 Events & Experiences
Winter Garden Farmers Market (104 S Lakeview Ave) — Saturdays year-round, 8 a.m.–1 p.m. Named one of the best in Florida, it’s a feast for the senses—local produce, flowers, baked goods, and music.
Garden Theatre (160 W Plant St) — A restored 1930s movie palace turned performing arts venue. Check their schedule for plays, concerts, and classic film nights.
SoBo Art Gallery (127 S Boyd St) — Home to the Winter Garden Art Association, featuring rotating exhibits and community workshops.
Festivals: From Blues & BBQ to Light Up Winter Garden, the town celebrates year-round with family-friendly events that never feel overrun.
📍 Featured Locations
Edgewater Hotel — Restored 1920s hotel in the heart of downtown
99 W Plant St • historicedgewater.com
Ruby & Rust — Locally owned boutique with vintage and modern finds
49 S Main St • rubyandrust.com
Adjectives Market — Marketplace for vintage, art, and design
131 W Plant St • shopadj.com
Crooked Can Brewing Co. — Brewery inside Plant Street Market
426 W Plant St • crookedcan.com
Prairie House Coffee Co. — Beloved small-town coffee shop
4 N Tubb St • prairiehousecoffee.com
7 Things You Can’t Miss in Apopka, Florida
Just down the road from Orlando is a city known for its thriving plant nurseries and unbelievable natural beauty. Near the community of Apopka you’ll find a number of spots where you can get in touch with nature, from clear springs to a farm where you can get lost in a corn maze during the autumn months. In this video, Chad Gallivanter highlights 7 things you can't miss near Apopka, Florida.
Exploring Cassadaga: A Spiritual Retreat With a Spooky Twist
If you are looking for a unique and mystical destination in Florida, you might want to check out Cassadaga, a small place just off I-4 known as the Psychic Capital of the World. Cassadaga is home to the largest Spiritualist community in the Southern United States, where you can find mediums, psychics, and other practitioners of the paranormal. But Cassadaga is not just a place for fortune-telling and ghost-hunting; it is also a place for history, nature, art, and culture.
8 Things You Should Know Before Visiting the Manatees at Blue Spring State Park
About an hour drive northeast from the theme parks of Orlando is a place of unspoiled beauty, where in cooler months, you’re almost guaranteed to see Florida’s most beloved marine animal.
Off Interstate 4 in the community of Orange City is Blue Spring State Park. The park covers more than 2,600 acres, including the largest spring on the St. Johns River. The park is a designated manatee refuge and the winter home to a population of West Indian Manatees.
From mid-November through mid-March, several hundred manatees flock to the constant 72-degree spring water. Visitors from all over the world descend on the park to get a better look at this awe-inspiring creature.
Today’s video is dedicated to the sea cow. We’re running down the 8 things you should know before visiting the manatees at Blue Spring State Park.
Best Stops Along I-4 Between Orlando and Daytona Beach
Starting on the west side of Florida in Tampa, running through the heart of downtown Orlando and terminating in the east with Daytona Beach is Interstate 4.
With the final stretch of the highway completed in 1965, it roughly follows the original path of the Sanford-Tampa Rail Line built by Henry Plant in the mid-1880s.
Spanning just over 130-miles, I-4 is known as one of the most heavily-traveled tourism corridors in the nation. The three major Orlando theme parks are just off the route along with other attractions, hotels, restaurants, and plenty more fun things to do.
In this video, we’re traveling a section of the highway to show you what we think are the best stops along I-4 between Orlando and Daytona. Well-known places and some maybe you’ve never heard of.
Best Things to See and Do in Winter Garden
Minutes from the gates of the Magic Kingdom is a city with an authentic Main Street that would make Mr. Disney himself proud.
The Main Street here in Winter Garden is called Plant Street, believed to have been named for the 19th century rail tycoon Henry B. Plant. He was responsible for developing and promoting the west coast and central sections of Florida.
Henry B. Plant, Florida Railroad Tycoon
At one time, tracks ran through the heart of town. But, you won’t find any locomotives coming through the downtown area today. Instead, the West Orange Trail splits the historic district, providing a place where folks can ride bicycles under the blue Florida skies.
Our most recent visit to Winter Garden coincided with one of the town’s most popular annual events, Spring Fever in the Garden. This huge community celebration puts the spotlight on historic downtown Winter Garden with all types of fun activities along Plant Street.
In this episode, we show you around this town we love so much and provide a few tips on what you should see and do when you’re in Winter Garden.
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Hours of Operation
OPEN
Tuesday through Saturday
11:00am until 3:00pm
CLOSED
Sunday and Monday
Free admission.
Donations appreciated.
Masks are optional.
ADDRESS101 S. Boyd St, Winter Garden, FL 34787
WEBSITE
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CONTACT
407.877.GRDN (4736)ADDRESS
160 West Plant Street
Winter Garden, Florida 34787
Best Things to See & Do in Sanford
Sanford, Florida is a community known for its tree-lined streets, neighborhoods with beautiful homes dating back a century, and a downtown full of mom and pop shops, small eateries, and a huge selection of places where you can grab a beer or some wine.
It’s also a festival city that thrives during special events which occur throughout the year.
Our last visit was the same day as Sanford Porchfest, an annual celebration of live music that recalls the days of porch jam sessions. This community-building event serves as the backdrop for our latest episode featuring the best things to see and do in one of Central Florida’s most popular places to live, Sanford.
12 Things You Should Experience This Fall in Central Florida
Pumpkin Patches & Fall Festivals
Fall Festival at Southern Hill Farms
16651 Schofield Rd, Clermont, FL 34714
Held Thursdays through Sundays til November 7th, the Fall Festival at Southern Hill Farms offers jolly Jumbo Jack carving pumpkins, S’mores around the fire pit, live music, food trucks and tasty apple cider donuts.
Tickets for this event must be purchased online in advance.
A Lot of Pumpkins at Santa’s Farm & Christmas Tree Forest
35317 Huff Rd, Eustis, FL 32736
Weekends October 2nd through Halloween and select weekdays, A Lot of Pumpkins at Santa’s Farm in Eustis is a fun event for the entire family.
Pumpkins are fresh picked and then displayed in a shaded lot to preserve their freshness.
Trick or Treat stations are set up throughout the farm and family-friendly costumes are welcome.
Pumpkin Ponderosa at Showcase of Citrus
5010 US-27, Clermont, FL 34714
A daily event with free admission and free parking is the Pumpkin Ponderosa at Showcase of Citrus in Clermont.
Families can pick their perfect pumpkin, make arts and crafts, play outdoor games, and go on hayrides.
There are even spooky fall adult beverages at two open-air bars.
Club Lake Fall Festival & Pumpkin Patch
3403 Rock Springs Rd, Apopka, FL 32712
Open four days a week Thursday through Sunday, the Club Lake Fall Festival and Pumpkin Patch in Apopka features hay rides, corn mazes, play areas, a country store and a pumpkin patch.
Pricing
THURSDAY – FRIDAY is $6.95 per person
SATURDAY – SUNDAY is $13.95 per person (Hayrides Included)
Infants are FREE
Corn Mazes
Long and Scott Farms
26216 County Rd 448A, Mt Dora, FL 32757
The oldest corn maze in the area can be found at Long and Scott Farms in Mount Dora. Year after year, the 6.5-acre corn maze has a unique themed design that is both fun and educational for the entire family.
There’s also a playground, market and cafe on-site.
Online ticket purchases are strongly encouraged.
Lake Catherine Farms
5849 Lake Catherine Road, Groveland, Florida 34736
Prices:
Corn maze $6 per person Friday through Sunday September 24- October 30
Fridays from 6pm-10pm, Saturdays from 10am-10pm and Sundays from 10am-5pm
Children 3 and under free
Fox Squirrel Corn Maze
3002 Charlie Taylor Rd N, Plant City, FL 33565
October 9th-24th, 10am til 5pm (Saturday and Sunday only)
18 AND OLDER: $11+TAX
3 TO 17: $10+TAX
2 AND UNDER: FREE
* Admission price includes unlimited maze, hayride games and more.
* NO PETS ALLOWED (except service animals)
* FREE Parking
* Pumpkins for sale* (Come get them while they last)
* Closed toed shoes advised
Phantasmagoria
Did you know Central Florida has its very own Victorian/Steampunk storytelling troupe?
Phantasmagoria draws you into their dark carnival of dance, explosive stage combat and danger arts for a visually addictive experience.
Renninger’s Marketplace Special Events
Renninger's Florida Twin Markets
20651 US 441, Mount Dora, FL 32757
Fall in the Field
Saturday, Oct 2, 2021 & Sunday, October 3, 2021
9:00 AM - 5:00 PM
This annual event is filled with an amazing array of “fall finery” displayed by some of the best primitive dealers in the Southeast. Dealers filling both pavilions and all the tents across the antique center with fall treasures, wonderful primitives and antiques.
FREE ADMISSION
FREE PARKING
Rain or Shine
Florida Military Collectors’ Show
October 9, 2021
The Florida Military Collectors’ show is a one-day event on Saturday, from 9:30 AM to 4:30 PM. It is one of the largest all-military collectibles shows in the South East and averages over 100 tables. The show features military antiques, relics, and memorabilia from historic conflicts to modern fighting forces.
FREE ADMISSION
FREE PARKING
Steampunk & Industrial Show
October 16 & 17, 2021
9:00 AM - 5:00 PM
Music, food, vendors, bands, camping, costume contest, interactive play and more.
FREE ADMISSION
FREE PARKING
Fall Country Jamboree at Barberville Pioneer Settlement
1776 Lightfoot Ln, Barberville, FL 32105
November 6th & 7th
9 am — 5 pm Saturday
9 am — 4 pm Sunday
Step back in time to the pioneer days at the Fall Country Jamboree.
Held the first weekend of November at the Barberville Pioneer Settlement, more than a hundred folk, bluegrass, and Gospel performers play and sing on several stages around the property.
There are also handmade arts and crafts along with a number of living history demonstrations.
This is a wholesome event for the entire family that’s very affordable.
Adults - $10
Children 6-12 - $5
Watch our video on the top things to do in Central Florida during fall.
Biketoberfest
Daytona Beach area
Thursday, October 14 - 17, 2021
daytonabeach.com/biketoberfest/
DeLand Indie Market Fall Edition
113 W Georgia Ave, DeLand, FL 32720
Sunday, October 3, 2021
11 AM - 5 PM
The DeLand Indie Market is a curated show held four times a year in downtown’s Artisan Alley. You’ll find vintage, boutique, art and handcrafted items from talented individuals who come from all over Florida just to be showcased at this event.
facebook.com/DelandIndieMarketatArtisanAlley/
Gatorland’s GATORS, GHOSTS AND GOBLINS
14501 S Orange Blossom Trl, Orlando, FL 32837
Looking for a safe, fun Halloween event for the entire family?
Gators, Ghosts and Goblins at Gatorland is my favorite Halloween event of all the major attractions in the area.
This special event is included with your regular park admission to Gatorland on weekends during October starting October 9th.
Children and adults are allowed to wear family-friendly costumes as long as they’re not scary or gory.
You can meet Gatorland’s Skunk Ape, participate in Frank & Stein’s Ooky Kooky Octoberfest featuring an undead polka band and go through the Swamp Ghost Monster Museum.
There’s also multiple themed haunt zones, interactive characters and a Children’s Halloween Costume Parade.
Best of all, Florida residents receive half-off single day admissions through October 31st.
Cassadaga, “The Psychic Capital of the World”
Is there any better place to spend a day in October than the one that claims to be the psychic capital of the world?
At the Cassadaga Spiritualist Camp, guided tours of this small Victorian-era community are offered, educating visitors about its mysterious beginnings.
There’s also a “Find the Spirits” Tour after dark when you can learn how manifestations of Spirit are investigated. Digital cameras and paranormal equipment are encouraged.
A third tour called “Encounter Spirit Night Tour” walks visitors through energy “hot spots” where orbs are often said to be captured on digital cameras.
Ticket prices range from $15 to $25 per adult. Check out the camp’s official website for tour information.
Eco Tours and Airboat Rides
Almost any day is a good day to go for a boat ride in Florida.
But there’s something about the autumn air that makes a boat ride extra special.
We recommend learning more about the history and ecology of one of the state’s longest rivers by booking a St. Johns River Eco Tour out of DeBary.
This experienced company offers a variety of excursions at different price levels and time out on the water.
*Editor’s Note:
During this video’s production, St. Johns River Eco Tour announced on its website that it will be temporarily closed for maintenance September 26 - October 17, 2021.
Mount Dora Craft Fair
October 23 & 24, 2021
9 AM - 5 PM
Often referred to as Central Florida’s biggest and best annual craft festival, the Mount Dora Craft Fair is held the fourth weekend of October. More than 400 artisans from around the nation participate in this free event held on the streets of historic Mount Dora.
If you enjoy crafts, this is the festival for you. Visit the official event website for more information.
Watch a Rocket Launch
(dates subject to change)
If you’re lucky, you might be able to catch a rocket launch at Kennedy Space Center.
As of this video’s production, there are two launches scheduled at the Cape in October, the second one slated for October 31st.
NASA’s SpaceX Crew-3 mission will launch four astronauts to the International Space Station.
Details on launch viewing packages have not been released and launch information is subject to change.
Go to the KSC website for the latest information.
No Earlier Than: October 16, 2021
Mission: Lucy Mission
Description: Launching from Kennedy Space Center in Florida, Lucy will be the first space mission to study the Trojan asteroids associated with the planet Jupiter. Lucy will complete a 12-year journey to eight different asteroids which hold vital clues to deciphering the history of the solar system.
Targeted Date: October 31, 2021
Mission: NASA's SpaceX Crew-3 Mission to the International Space Station
Description: NASA’s SpaceX Crew-3 mission will launch four astronauts aboard a Crew Dragon spacecraft on a Falcon 9 rocket from Launch Complex 39A at Kennedy Space Center to the International Space Station. Assigned to the mission are NASA astronauts Raja Chari, Tom Marshburn, and Kayla Barron, and European Space Agency astronaut Matthias Maurer.
