Fall Activities in The Villages
Keep an eye out for the Acorn popping up around town—it's your sign that a business, event, or location is getting in the spirit of the season!
October
Happenings
Seasonal
Highlights
Explore featured fall and holiday experiences happening throughout the community.
Halloween at All Squares
Festive fun is brewing at The Villages Town Squares this Halloween. Read the post and explore each Square’s unique themed costume contest, live music lineup, and seasonal drink specials to start planning your Halloween celebration.
Dragon Boat Rodeo
Get ready for an action-packed morning of fire on the water! Watch the Grand Masters Dragon Boat Club teams and other Villager teams go head-to-head in a series of races on Central Lake during the 1st Annual Dragon Boat Rodeo.
Business Spotlight
Marco's Pizza
Margarita pizza is back, and New York style Pepperoni pizza staying for the season! Enjoy festive decor, fantastic flavors, and find “Hot Deals” for the holidays!
Business Spotlight
Peterbrooke Chocolatier
Enjoy decadent seasonal fun through the end of the year! Discover carefully-crafted Halloween baskets and treats, or specialty chocolate centerpieces and place settings for Thanksgiving.
Be sure to catch the customer appreciation party on Black Friday, from 2 PM – 6 PM, and enter the raffles for exciting prizes being given out throughout the holiday season! And for folks looking for a little extra holiday magic, be sure to sign up for the specialty decorating class happening in early December – or, book your own private party, starting at $35.00 per person with a minimum of 8 attendees!
Business Spotlight
Changes Boutique
Enjoy festive decor, half-off discounts, and exciting holiday events happening in-store!
- Fashion Show on Oct 23 | 1-3PM | Enjoy special discounts, with food and beverages available
- Halloween Costume Party on Oct 30 | Gift Certificate awarded for Best Dressed. with food & beverages available
- Fashion Show on Nov 13 | 1-3PM | Enjoy special discounts, with food and beverages available
- Black Friday Sale on Nov 27 | More info to come
Flashmob FunAddicts
- 10/19 – 5:45 pm at Spanish Springs
- 10/21 – 5:45 pm at Lake Sumter Landing
- 10/26 – 5:45 pm at Brownwood
Business Spotlight
Amerikanós Grille
Welcome Back Snow Bird Special!
Sip a drink while you enjoy a show. Enjoy our Flaming Saganaki Cheese paired with hand crafted cocktail options. These include our Caramel White Russian, Cucumber Mint Martini, Vanilla Mule, and Berry Splash for $17.
Business Spotlight
Think Pink Saturdays
Visit Stretch Zone wearing pink and you’ll receive a free stretch gift card valued at $50! Plus, for every guest, Stretch Zone will donate a stretch to the Breast Cancer Foundation of Central Florida. Limited to the first 20 guests each Saturday.
Fall Golf Expo
Discover top golf brands showcasing their newest products, innovations, game-improvement solutions. Whether you’re looking to upgrade your equipment or learn about the latest trends, the Golf Expos is your destination for all things golf.
The Villages Twirlers
- 10/21 – 10:45am at Spanish Springs
Shop & Dine Saturdays
Fall Entertainment Hours
- Sun-Thu: 5-9pm & Fri-Sat: 6-10pm
Eastport
- Daily: 6-10pm
2026 Pro Shootout
Follow ten professional players as they match off to see who takes home the coveted Pro Shootout belt.
Fall Flavors
Kick-off the Fall Season of Celebration by visiting one of our Town Square Bar Huts.
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Singles$8
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Doubles$10.50
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Mocktails$6 Medium • $7.50 Large
• Cranberry Mule
• Witch's Brew
• Pumpkin Spike
• Vampire's Kiss*
*Only at Spanish Springs
• Cranberry Mule
• Cranberry Mule Mocktail
Drink of the Month
Stir up some fall fun in #TheVillages! Sip on a Witch’s Brew or Cranberry Mule Mocktail at Happy Hour while enjoying live music, great friends, and seasonal celebrations around The Squares.
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Singles$8
-
Doubles$10.50
-
Mocktails$6 Medium • $7.50 Large
Business Spotlight
Bermuda Bay Clothing
Stop in during Shop & Dine Saturdays to explore seasonal offerings and special savings.
Light Up The Villages
Featuring cheerful holiday music, dazzling lights, and special guests of honor ready to help bring the night to life, Light Up The Villages is here to help bring us closer together and enjoy the real magic of the holidays: spending time with our friends, family, and neighbors.
Seasonal Entertainment Hours
Spanish Springs
Lake Sumter Landing
Brownwood
Sawgrass Grove
Eastport
October
Sun
Mon
Tue
Wed
Thu
5pm-9pm
5pm-9pm
5pm-9pm
5pm-9pm
Fri
Sat
6pm-10pm
6pm-10pm
6pm-10pm
6pm-10pm
6pm-10pm
November
Sun
Mon
Tue
Wed
Thu
Fri
Sat
5pm-9pm
5pm-9pm
5pm-9pm
5pm-9pm
5pm-9pm
Seasonal Entertainment Hours
Spanish Springs
October
Sun-Thu
5pm-9pm
Fri-Sat
6pm-10pm
November
Mon-Sun
5pm-9pm
Lake Sumter Landing
October
Sun-Thu
5pm-9pm
Fri-Sat
6pm-10pm
November
Mon-Sun
5pm-9pm
Brownwood
October
Sun-Thu
5pm-9pm
Fri-Sat
6pm-10pm
November
Mon-Sun
5pm-9pm
Sawgrass Grove
October
Sun-Thu
5pm-9pm
Fri-Sat
6pm-10pm
November
Mon-Sun
5pm-9pm
Eastport
October
Mon-Sun
6pm-10pm
November
Mon-Sun
5pm-9pm
