Events calendar
The special nights, holiday lightings, headline shows and nearby-town events worth planning around, in one place. Every listing links to the page it was checked against, with the date it was checked.
Updated October 16, 2026 · 44 upcoming events · Refreshed weekly by Cristian Gonzalez, REALTOR®, eXp Realty
As of October 16, 2026, this calendar lists 44 upcoming events in and around The Villages through December 31, 2026; 28 are free. Holiday lightings, special square nights, headline shows and nearby-town events are all here. Every listing links to its source and the date it was checked.
Free live music plays on the town squares every night of the year. The calendar lists the special events on top of that.
Comparing communities? Events around Middleton and Wildwood covers the all-ages side of Sumter County.
Friday, October 16, 2026
Check-in 4 p.m., show 5 p.m. · $35 · Ticketed
Historic Baker House, 6106 CR 44A, Wildwood FL 34785
Final night of a dinner theater mystery staged inside Wildwood's historic Baker House. Advance registration is required.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 16, 2026
5 to 8 p.m. · Free · Open to the public
Brownwood Paddock Square and Lake Sumter Landing Market Square, 2726 Brownwood Blvd, The Villages FL
Local car clubs line up classics, convertibles, Mercedes, BMW Z models and Thunderbirds on the squares. December dates not yet posted.
Source: The Villages Entertainment: Car Shows, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 16, 2026
October: 5 to 9 p.m. Sun to Thu, 6 to 10 p.m. Fri and Sat (Eastport 6 to 10 p.m. daily); November: 5 to 9 p.m. daily · Free · Open to the public
Spanish Springs, Lake Sumter Landing, Brownwood, Eastport and Sawgrass Grove, The Villages
Every town square hosts live bands outdoors each evening, year round, with no admission charge. Bring a chair; bar huts serve seasonal drinks. Hours shift by month.
Source: The Villages (Seasons of Celebration: Fall), checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 17, 2026
9 a.m. to 1 p.m. · Free · Open to the public
Brownwood Paddock Square, 2726 Brownwood Blvd, The Villages FL
Weekly open-air market with produce, baked goods and local vendors on Brownwood Paddock Square. Golf cart parking is on Kiessel Road and W Torch Lake Drive.
Source: The Villages Entertainment: Hometown Market, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 17, 2026
7 to 9:30 p.m. · Free · Open to the public
Snooky Park, 120 W Lady Lake Blvd, Lady Lake FL
Lady Lake turns Snooky Park into a nighttime haunted walking trail for the Halloween season.
Source: Town of Lady Lake calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, October 18, 2026
6:30 p.m. · Ticketed · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
Actor and longtime military supporter Gary Sinise brings his Graceful Warrior program to The Sharon.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
October 19, 2026 to October 26, 2026
5:45 p.m. · Free · Open to the public
Spanish Springs (Oct 19), Lake Sumter Landing (Oct 21), Brownwood (Oct 26), The Villages
A resident dance troupe pops up with surprise flash mob routines on three town squares over one week. Arrive a few minutes early for a good view.
Source: The Villages (Seasons of Celebration: Fall), checked October 16, 2026. Google Calendar · Apple or Outlook
Tuesday, October 20, 2026
9 a.m. to 2 p.m. · Free · Open to the public
Rolling Acres Sports Complex, 250 Rolling Acres Rd, Lady Lake FL 32159
Weekly Tuesday market with farm produce, crafts and local vendors, running through December.
Source: Town of Lady Lake calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, October 21, 2026
7 p.m. · Ticketed · Ticketed
Savannah Center, The Villages
A Halloween season illusion show with spooky magic and stage effects.
Source: The Villages Entertainment, checked October 16, 2026. Google Calendar · Apple or Outlook
October 22, 2026 to October 31, 2026
4:45 p.m. Oct 22; 6:45 p.m. Oct 29 to 31 · Free · Open to the public
Sawgrass Grove (Oct 22), Eastport (Oct 29), Brownwood (Oct 30), Spanish Springs (Oct 31), The Villages
Costumed resident dancers perform the famous Thriller routine across four town squares, finishing on Halloween night at Spanish Springs.
Source: The Villages (Seasons of Celebration: Fall), checked October 16, 2026. Google Calendar · Apple or Outlook
October 23, 2026 to October 24, 2026
10 a.m. to 3 p.m. · Free · Open to the public
Championship golf shops and Golf Academy locations, The Villages
Two days of equipment demos, club fittings and deals across The Villages golf shops and practice centers.
Source: The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, October 23, 2026
6 to 9 p.m. · Free · Open to the public
Wildwood Community Center, 6500 Powell Rd, Wildwood FL 34785
Free Halloween night out with hayrides, food trucks and a kids' zone.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 24, 2026
5:30 to 8 p.m. · Free · Open to the public
Guava Street Athletic Complex, 221 W Guava St, Lady Lake FL
A gentle, family style Halloween evening hosted by the Town of Lady Lake.
Source: Town of Lady Lake calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 24, 2026
6:30 to 9 p.m. · Ticketed · Ticketed
Gardenia Center, 205 W Berckman St, Fruitland Park FL
New city event pairing local restaurants and beverage vendors with live blues. Advance tickets sold through Eventbrite.
Source: City of Fruitland Park, checked October 16, 2026. Google Calendar · Apple or Outlook
October 28, 2026 to October 29, 2026
4 and 6 p.m. · $20 · Ticketed
Historic Baker House, 6106 CR 44A, Wildwood FL 34785
Evening ghost tours of Wildwood's historic Baker House. Advance registration is required.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, October 31, 2026
6 to 10 p.m. · Free · Open to the public
Spanish Springs, Lake Sumter Landing, Eastport and Brownwood, The Villages
Each square has its own theme (Wild West, Decades, Icons and Idols, Home State) with live music and costume contests. Winners are named at 8 p.m.
Source: The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, November 1, 2026
7 p.m. · Ticketed, from $50 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
The seven time GRAMMY winner and Kennedy Center honoree performs hits spanning soul, pop and gospel.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, November 7, 2026
3:30 p.m. · Free · Open to the public
Eastport, 7025 Central Lake Dr, The Villages FL 34762
Big screen college football on the Eastport square. Bring your own chair.
Source: The Villages Entertainment: Seasonal Events, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, November 8, 2026
9 a.m. to 4 p.m. · Free · Confirm access with the host
Soaring Eagle Softball Complex, The Villages
A day of softball kicking off The Villages' Veterans Day week of events.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
11 a.m. · Free · Open to the public
Veterans Memorial Park at Spanish Springs, The Villages
The community's main Veterans Day ceremony, held at the memorial park beside Spanish Springs Town Square.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
1 p.m. to sunset · Varies · Confirm access with the host
Lake Sumter Line dock, Lake Sumter Landing, The Villages
Lake Sumter Line cruises run through the afternoon on Veterans Day, with veterans welcomed aboard.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
5 p.m. · Free · Open to the public
All town squares, The Villages
Evening tributes on every square honor those who served. Veterans also get 25 percent off select ticketed shows at the Savannah Center and The Tracy.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
7 p.m. · Ticketed, from $25 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
Story, music and theater from an FDNY survivor and an Afghanistan combat veteran, backed by a live jazz ensemble. Staged on Veterans Day.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
7 p.m. · Varies · Ticketed
The Tracy, The Villages
Heart of Florida, barbershop and Villages High School choirs and band perform a Veterans Day program.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, November 11, 2026
Free · Open to the public
Wildwood City Hall, 100 N Main St, Wildwood FL 34785
Wildwood displays tributes to local veterans at City Hall for Veterans Day.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Thursday, November 12, 2026
4 and 7 p.m. · Ticketed, from $60 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
The hitmaking producer and the singer and actress share songs and stories in two performances.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Thursday, November 12, 2026
5 p.m. · Free · Open to the public
Farragut Softball Complex, The Villages
Outdoor public showing of the WWII bomber film. Registration required; it opens Oct 29 at DistrictGov.org or At Your Service centers.
Source: The Villages: Veterans Day in The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, November 14, 2026
8 a.m. to 1 p.m.; races start 9 a.m. · Free · Open to the public
Central Lake at Eastport (viewing on Sunset Island), 6980 Central Lake Drive, The Villages FL
Grand Masters Dragon Boat Club and Villager teams race on Central Lake. Opening ceremony at 8 a.m., performances, food on Sunset Island and awards after.
Source: Village Center CDD flyer via TheVillages.com, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, November 15, 2026
3 and 7 p.m. · Ticketed, from $85 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
The holiday touring favorite brings its signature Christmas sound and light show for two performances.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, November 20, 2026
12 to 5 p.m. · Free · Open to the public
Cane Garden, Hibiscus Nine, The Villages
Golf professionals compete in an afternoon shootout format at Cane Garden.
Source: The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, November 21, 2026
6 to 8 p.m. · Free · Open to the public
Snooky Park, 120 W Lady Lake Blvd, Lady Lake FL
Lady Lake's holiday lighting celebration at Snooky Park. The town's Christmas parade was canceled this year over public safety costs.
Source: Town of Lady Lake calendar, checked October 16, 2026. Google Calendar · Apple or Outlook
Sunday, November 29, 2026
7 p.m. · Ticketed, from $25 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
A reimagined Nutcracker told through glowing costumes, movement and light.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
December 1, 2026 to December 29, 2026
Tue, Thu, Sat at 4, 5 and 6 p.m.; Sun at 1, 2 and 3 p.m. · $15 · Ticketed
Historic Baker House, 6106 CR 44A, Wildwood FL 34785
Guided tours of the historic home decorated for Christmas. Private tours $20. Advance registration required.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Tuesday, December 1, 2026
5 to 9 p.m. · Free · Open to the public
Brownwood, Eastport, Lake Sumter Landing and Spanish Springs, The Villages
The official start of the holiday season, with simultaneous lighting celebrations, holiday music and special guests on every town square.
Source: The Villages, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, December 4, 2026
Festival 5 p.m., parade 6 p.m., tree lighting 7:30 p.m. · Free · Open to the public
Wildwood City Hall, 100 N Main St, Wildwood FL 34785
Downtown Wildwood's holiday night: a festival, Christmas parade, tree lighting ceremony, then visits with Santa from 8 to 9 p.m.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Thursday, December 10, 2026
7 p.m. · Ticketed, from $46 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
The classic rock band behind a string of 1970s hits plays The Sharon.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, December 11, 2026
5:30 p.m. · Free · Open to the public
Fruitland Park City Hall, 506 W Berckman St, Fruitland Park FL 34731
City holiday celebration with a DJ, vendors, food trucks, bounce houses and a visit from Mr. and Mrs. Claus, who traditionally arrive by fire truck.
Source: City of Fruitland Park, checked October 16, 2026. Google Calendar · Apple or Outlook
December 12, 2026 to December 13, 2026
10 a.m. to 5 p.m. · Free · Open to the public
Lake Sumter Landing Market Square, 1000 Lake Sumter Landing, The Villages FL 32162
Two days of handmade gifts from local artisans, food trucks and live entertainment on the square.
Source: The Villages Entertainment, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, December 12, 2026
3 p.m. · Free · Open to the public
Eastport, 7025 Central Lake Dr, The Villages FL 34762
Watch the Army Navy game on the Eastport square. Bring your own chair.
Source: The Villages Entertainment: Seasonal Events, checked October 16, 2026. Google Calendar · Apple or Outlook
Friday, December 18, 2026
6 to 8 p.m. (sensory friendly hour 5 to 6 p.m.) · Free · Open to the public
Wildwood Community Center, 6500 Powell Rd, Wildwood FL 34785
Free evening of cookies and photos with Santa, with a quieter sensory friendly hour beforehand.
Source: City of Wildwood July to Dec 2026 Program Guide, checked October 16, 2026. Google Calendar · Apple or Outlook
Saturday, December 19, 2026
Free · Open to the public
Brownwood, Eastport and Spanish Springs, The Villages
A glow themed night on three squares; guests are encouraged to wear neon or light up accessories. Times not yet announced.
Source: The Villages (Seasons of Celebration: Fall), checked October 16, 2026. Google Calendar · Apple or Outlook
December 20, 2026 to December 21, 2026
3 and 7 p.m. both days · Ticketed, from $35 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
Holiday edition of the Tony winning musical about the Sun Records jam session with Elvis, Johnny Cash, Jerry Lee Lewis and Carl Perkins.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Wednesday, December 23, 2026
7 p.m. · Ticketed, from $40 · Ticketed
The Sharon Performing Arts Center, 1051 Main Street, The Villages FL 32159
Acrobats and aerialists perform to familiar seasonal music in a winter wonderland setting.
Source: The Sharon Performing Arts Center, checked October 16, 2026. Google Calendar · Apple or Outlook
Thursday, December 31, 2026
5 to 9 p.m. · Free · Open to the public
Eastport Center Stage, 6980 Central Lake Drive, The Villages FL
Eastport's calendar marks New Year's Eve with The Brothers Jukebox on Center Stage. Any countdown or extra programming has not been announced yet.
Source: Eastport Monthly Happenings calendar (The Villages), checked October 16, 2026. Google Calendar · Apple or Outlook
Visit before you decide
The fastest way to know if a place fits is to be there on a real night. I am Cristian Gonzalez, a REALTOR® with eXp Realty, born and raised in Marion County and a Navy Veteran. I represent buyers independently, and I will plan the visit around what you want to see.
Tell me the dates you will be here. I will build you a visit plan around these events: which squares to see, which villages to drive, and a short list of homes worth a look.