What's Happening This Week in The Villages?

Welcome back, neighbors: the week of November 10-16, 2026 in The Villages is packed with reasons to head out, starting with a Veterans Day tribute on Wednesday and a dose of holiday magic with Mannheim Steamroller on Sunday, plus two car shows, a sailing regatta, and free live music on the squares just about every single night. Here is your warm, local guide to it all, courtesy of your neighborhood Realtor, Lili Whittington.

Top 3 Picks of the Week

Mannheim Steamroller

Sunday, November 15 at 3:00 PM · Sharon L. Morse Performing Arts Center, 1051 Main St, The Villages, FL 32159

Holiday-music legends in concert; ticketed event.

Veterans Day Concert

Wednesday, November 11 at 7:00 PM · Tracy Performing Arts Center at The Villages High School

A community tribute honoring America's veterans.

Friday Night Car Show

Friday, November 13, 5:00-8:00 PM · Lake Sumter Landing Market Square, 1020 Lake Sumter Landing, The Villages, FL 32162

Classic cars, music, and drinks on the square, hosted by the Villages Classic Automobile Club. Free to attend.

Your Week, Day by Day

Tuesday

November 10

Trivia Tuesday at Sawgrass Grove , 12:00-2:00 PM, 766 Marilee Pl, The Villages, FL 34785

Free daytime trivia.
Zee-R Band at Brownwood Paddock Square , 5:00 PM, 2726 Brownwood Blvd, The Villages, FL 32163

Free live music.
Rocky and The Rollers at Lake Sumter Landing Market Square , 5:00 PM, 1020 Lake Sumter Landing

Free; high-energy music from all eras.
Bobby Blackmon & The B3 Band at Eastport , 5:00-9:00 PM, 7025 Central Lake Dr, The Villages, FL 34762

Free soul-blues dancing.
Street Talk at Spanish Springs Town Square , 5:00 PM, 1051 Main St, The Villages, FL 32159

Free live music.

Wednesday

November 11

Veterans Day Concert at Tracy Performing Arts Center at The Villages High School , 7:00 PM

A community tribute honoring America's veterans.
Daisy Fever at Lake Sumter Landing Market Square , 5:00-9:00 PM, 1020 Lake Sumter Landing

Free live music.

Thursday

November 12

An Intimate Evening with David Foster and Katharine McPhee with Special Guest Fernando Varela at The Sharon , 4:00 PM, 1051 Main St, The Villages, FL 32159

Ticketed.
Penta at Lake Sumter Landing Market Square , 5:00-9:00 PM, 1020 Lake Sumter Landing

Free rock, blues, and funk.
Think Big Band at Eastport , 5:00-9:00 PM, 7025 Central Lake Dr

Free classic rock, Motown, blues, country, and dance tunes.

Friday

November 13

Friday Night Car Show at Lake Sumter Landing Market Square , 5:00-8:00 PM, 1020 Lake Sumter Landing, The Villages, FL 32162

Classic cars, music, and drinks on the square, hosted by the Villages Classic Automobile Club. Free to attend.
AndrewLuv and the Franchise Players Band at Brownwood Paddock Square , 5:00-9:00 PM, 2726 Brownwood Blvd

Free live music.

Saturday

November 14

Soling 1M Open Regatta at Lake Mira Mar , 10:00 AM

Sailing race, free to watch.
MoonShine Abby at Brownwood Paddock Square , 5:00-9:00 PM, 2726 Brownwood Blvd

Free live music.
V4V presents: Leesburg Blues Brothers at Epic Theatres Old Mill Playhouse , 1000 Old Mill Run, The Villages, FL 32162

Ticketed show.
Time Machine at City Fire Sumter Landing , 7:30 PM, 1018 Canal St, The Villages, FL

Live music at the restaurant.

Sunday

November 15

Mannheim Steamroller at Sharon L. Morse Performing Arts Center , 3:00 PM, 1051 Main St, The Villages, FL 32159

Holiday-music legends in concert; ticketed event.

Monday

November 16

Monday Night Car Show at Brownwood Paddock Square , 5:00-8:00 PM, 2726 Brownwood Blvd

Hosted by the Villages BMW-Z Club. Free to attend.
Boozy Bingo at Sawgrass Grove , 6:00-10:00 PM, 766 Marilee Pl

Free music bingo with prizes; markers and boards provided.

A Week to Get Out and Enjoy

I hope this week's lineup gives you plenty of excuses to hop in the golf cart, meet a neighbor, and enjoy everything our community does best. From honoring our veterans on Wednesday to singing along to holiday classics on Sunday, there is truly something for everyone.

And if you are just visiting, thinking about snowbirding here, or ready to make The Villages your home, I would love to help you find the right place in it.

Thinking about buying or selling in The Villages? Reach out to Lili Whittington for honest, local guidance on The Villages real estate, in English or Spanish.

352-715-3515 Book a Time with Lili

Event details were verified at the time of writing; always confirm dates and times before you go.