Welcome to Thursday Morning, Orlando!
Dang. The amount of outstanding events taking place around Greater Orlando this weekend is overflowing. It’s like trying to fit 10lbs of stuff into a 5lb bag, making this issue particularly challenging because I try to curate and bring you the coolest things to do in a nice little package. But that's why you pay me the big bucks around here!
🎂 Wishing a very happy birthday to beautiful readers, Amanda Bolick and Teresa Suarez
- Bike 5 Main Streets
- MONSTER MILKY WAY
- Downtown Clermont's Beloved Harvest Festival
- + lots of weekend recs
Was this newsletter forwarded to you? Subscribe here.
Let’s roll!
- Philip
P.S. 🍲 Want some hawt community sourced foodie recommendations? Check out the Orlando Signal Restaurant Guide, right here.
🔥 You're going on a dinner adventure with five strangers who won't be strangers for long:
Join our first Dinner Club
We’re bringing together good people, good food, and good conversation in a city we all love.
The deets: Take a quick quiz. Get matched with five other OS readers you'll actually vibe with. Meet for dinner on Wednesday, October 29th at 6:30 PM at a mystery Milk District restaurant (we’ll reveal that morning). Then, optionally hit our casual after-get-together at a nearby venue.
- If you recently moved here, this is your shortcut to finding your people.
- If you’ve been here for years, we tend to isolate as we get older. Same routines, same circles. New people are fun. Meet them!
(Optional) At the end of the quiz, you can invite a friend or significant other to join. If they book their seat within 12 hours, they'll get matched to your table.
The logistics:
- Booking: Just 16 bucks per seat (100% supports Orlando Signal)
- Your meal: You pay for what you order at the restaurant
- What we do: Orchestrate everything. Book the restaurant, send reminders, sort every detail. You just show up.
🫵 Get Details & Start the Quiz →
3 QUICK NEWS BITS ⏲️
Pedal Your Way Through Orlando's Coolest Neighborhoods This Weekend
On Saturday, grab your bicycle and join the first-ever Bike 5 Main Streets ride, a 10-mile adventure through Central Florida's most vibrant districts. Roll out at 10:00 AM from either Mead Botanical Garden in Winter Park or Orlando's Colonialtown Neighborhood Center.
Cruise through Mills 50, Thornton Park, The Milk District, Audubon Park Garden District, and Ivanhoe Village, stopping for coffee, vintage finds, or tacos.
Created by Bike/Walk Central Florida with the City of Orlando and Orlando Main Streets, this relaxed, guided ride welcomes everyone.
Experienced leaders ensure nobody gets left behind, just good vibes and great discoveries!
🚵♀️ Get more info about this ride, and register, right here.
A Symphony Sets Sail: 'One Piece' Gets Live Orchestral Treatment
The Grand Line is crashing into Central Florida, and it's bringing a full orchestra. Kicking off this Saturday, the Dr. Phillips Center turns into pirate paradise as ONE PIECE Music Symphony takes over with 50 musicians performing composer Kohei Tanaka's epic score beneath a massive 40-foot HD screen.
This "Films in Concert" adventure follows Monkey D. Luffy's wild quest to become King of Pirates, but cranked up to eleven with live brass and strings.
The manga juggernaut, 97 volumes and over 930 TV episodes strong, gets its greatest hits treatment as the orchestra literally blows the roof off.
It's anime storytelling with maximum volume and zero chill.
🎼 Ever hear of ONE PIECE? Check it out, right here.
Hey, You. Take a Hike…..This Weekend!
Forget fiery fall foliage. In Central Florida, fall arrives with something more precious: enjoyable weather.
As temperatures finally drop and humidity takes a hike (hehe, pun intended), Central Florida's trail systems become the playground they were meant to be. Wander through whispering pine forests, splash past wetlands teeming with life, duck under canopies of ancient oaks, and gaze across prairies where the horizon seems endless.
Gear up smart: grab a hiking partner, navigation tools, insect repellent, sun protection, trail snacks, and loads of H2O. And stick to the golden rule….snap memories, spend hours, but leave nature exactly as you found it.
From Wekiwa Springs' epic 13-mile networks to Black Bear Wilderness Area's in Sanford’s wild riverside loops, Spring Hammock's in Longwood’s chill boardwalks to Lake Louisa's rolling hills in Clermont, adventure awaits this season!
(Learn lots more about these hiking spots + many more with Patrick Connolly, right here)
WEEKEND SPOT HIGHLIGHT 🔦
MONSTER MILKY WAY BAR + BITES CRAWL
Source: The Milk District
📍The Milk District. 2406 E Washington St, Orlando, FL 32803. Map to this location.
🕐 Friday, October 24th, 6 p.m. - 10 p.m.
When darkness falls, over 100 costumed revelers descend upon the Milk District for the Monster Milky Way Bar + Bites Crawl.
Your wristband unlocks killer drink and bite specials at every stop, exclusive swag, a custom crawl map, and entry to the costume contest. Participants flow through in waves, ensuring immaculate vibes at each local haunt.
The catch? Tickets vanish faster than spirits at sunrise. Don't let your only nightmare be missing out.
👉 Check It Out
TOP 3 FUN RECS FOR THE WEEKEND 🍊
Wekiva Island’s Annual Halloween Party
Source: Wekiva Island
📍Wekiva Island. 1014 Miami Springs Drive, Longwood, FL 32779. Map to this location.
🕐 Saturday, October 25th, 7-10 p.m.
Rally your crew and unleash your most creative alter ego.
This 21+ riverside bash promises serious cash prizes for the best-dressed competitors, alongside haunting ambiance, specially crafted drink specials, and live music pulsing through the night.
Year after year, participants transform into show-stopping characters, driven by legendary prizes that make every costume detail count.
Prepare for a night where creativity reigns supreme.
👉 Get more info, right here
College Park JazzFest
Source: College Park Main Street
📍Enter at any one of eight entrance gates off Edgewater Drive. 648 Dartmouth St, Orlando, FL 32804. Map to this location.
🕐 Saturday, October 25th, 5-11 p.m.
For more than two decades, College Park JazzFest has been the neighborhood's can't-miss celebration.
Since 2002, this flagship College Park Main Street event transforms Edgewater Drive into an electrifying block party featuring 12 live bands across three stages, delivering jazz, R&B, and rock that keeps crowds dancing.
Locals arrive with lawn chairs and friends, but nobody stays seated long. Between sets, explore food trucks, dine at local restaurants, and browse open shops, it's the perfect blend of music, flavor, and community spirit.
👉 Get the full details
Downtown Clermont's Beloved Harvest Festival
Source: Downtown Clermont
📍Downtown Clermont. 752 W Montrose St, Clermont, FL 34711. Map to this location.
🕐 Saturday, October 25th, 10 a.m -11 p.m.
Clermont's cherished autumn tradition is back, turning downtown into a seasonal celebration.
This year's Harvest Festival features over 100 artisan vendors showcasing unique handcrafted treasures, plus a legendary costume contest welcoming both people and pets.
Families will enjoy a dedicated kids zone, live music filling the streets, and mouthwatering food trucks satisfying every craving.
A community gathering inviting everyone to savor fall's simple pleasures and create lasting memories together.
👉 Check it out, right here
MORE WEEKEND HAPPENINGS 🎭 🥁
Multi-Day
Boo Orlando! | Fri & Sat | Lake Nona | More
A Petrified Forest: Scream Park | Fri & Sat | Altamonte Springs | More
Dragon Nights: Hidden Treasure Quest | Fri & Sat | Leu Gardens | More
Earthquake at the Funnybone | Fri & Sat | I-Drive | More
Friday - 24th
Hauntingly Good Times at Lake Eola (Eolaween) | 4 p.m. | Downtown | More
History After Dark: Halloween Edition | 5 p.m. | Downtown | More
🔥 Ceiba BCA Night with Natasha Sofia | 6 p.m. | Lake Buena Vista | More
Boo! on Broadway | 6 p.m. | Kissimmee | More
Iam Tongi | 6 p.m. | Downtown | More
Boo Skate at the Ice Factory | 7 p.m. | Kissimmee | More
BOLO | 10 p.m. | Downtown | More
Burgundee | 7:30 p.m. | Wadeview Park | More
Saturday - 25th
🔥 Statement Series: A Fashion Networking Event | 3 p.m. | I-Drive | More
Windermere Craft Beer Fest: Re-Tapped | 4 p.m. | Windermere | More
Orlando Science Center After Dark | 8 p.m. | Downtown | More
Central Florida Veg Fest | 10 a.m. | Festival Park | More
Midnight Movies: Martyrs | 11:59 p.m. | Maitland | More
Race for Inclusion | 8 a.m. | Kissimmee | More
National Theatre Live: Mrs. Warren’s Profession | 11 a.m. | Maitland | More
UCF Knights Volleyball vs. Texas Tech Red Raiders Womens Volleyball | 1 p.m. | UCF | More
Sunday - 26th
🔥Books, Beef and Bucks 2025 | 10 a.m. | Winter Springs | More
Fall Festival | 10 a.m. | Kissimmee | More
Clermont Clay 15k & 5k | 7:30 a.m. | Clermont | More
Robert Redford Tribute: Butch Cassidy and the Sundance Kid | 12 p.m. | Maitland | More
Pulp City Sessions | 12 p.m. | Mills 50 | More
UCF Knights Mens Basketball vs. LSU Men's Basketball | 12 p.m. | UCF | More
FSYO's 69th Season Classical Opener, Part I | 2 p.m. | I-Drive | More
TalkDeath 2025 Halloween Cemetery Scavenger Hunt | 2:30 p.m. | Winter Park | More
TwoSet Violin | 3 p.m. | Downtown | More
R&B Renaissance 5 Year Anniversary | 6 p.m. | Downtown | More
Aly & AJ - Silver Deliverer Tour 2025 with Amanda Shires | 7 p.m. | I-Drive | More
🎭 Have an event to share?Submit it here.
THANKS!
🧠Interested in reaching smart readers like you? Grow with us right here.
🌟 Know a community superstar? Tell me about them, right here.
We’ll see you on Monday.
My Best,
Philip - Publisher, Orlando Signal
