Where can you still hear a live band at 9:30 on a Tuesday night in The Villages this month? Through Oct. 31, the answer is one place. Eastport's Center Stage runs from 6 to 10 p.m. every night of the week. Spanish Springs, Lake Sumter Landing, Brownwood and Sawgrass Grove end at 9 p.m. Sunday through Thursday.
Counting from tonight, Monday, Oct. 5, there are 19 Sunday-through-Thursday nights left in October. On each of them, Eastport is the only square with live music after 9. On Friday and Saturday nights all the squares run until 10, so Eastport's extra hour only exists on weeknights. Beginning Nov. 1, every Town Square and Sawgrass Grove moves to 5 to 9 p.m., seven nights a week.
The hour, laid out
The posted seasonal hours side by side make the weeknight gap clear.
| Location | October, Sun–Thu | October, Fri–Sat | Starting Nov. 1 |
|---|---|---|---|
| Eastport | 6–10 p.m. | 6–10 p.m. | 5–9 p.m. |
| Spanish Springs, Lake Sumter Landing, Brownwood, Sawgrass Grove | 5–9 p.m. | 6–10 p.m. | 5–9 p.m. |
An hour on a stage schedule only matters if there's somewhere to sit, eat and order a drink during it. This October, Eastport's restaurants and bars line up with that late window.
Which kitchens keep pace with the stage
Three Eastport spots set the shape of a weeknight evening. Their posted hours differ, and that changes how you'd plan the night.
Oak & Stone is scheduled to open Tuesday, Oct. 6, on Central Lake Drive. It's the brand's first Central Florida location and brings it to 10 locations across Florida and Texas. The official location page lists Sunday through Thursday hours of 10 a.m. to 10 p.m. and Friday and Saturday hours of 10 a.m. to 11 p.m. On a weeknight, its kitchen and the Center Stage music both wrap up at 10.
The restaurant is 6,049 square feet. It seats 78 indoors and 38 on an indoor-outdoor bar and patio, which includes two 12-top fire feature tables. The self-pour tap wall offers 36 drafts, 16 wines and 14 bourbons. If you haven't used a self-pour wall before, you ask staff for a tap card and scan it at the tap screen to unlock a pour. The screen shows the drink, its ABV, its bitterness rating in IBUs and its price per ounce. The system measures to one-tenth of an ounce and charges only for what you pour, so a taste of an unfamiliar bourbon costs a few ounces' worth, not a full glass.
Oak & Stone doesn't take reservations, but you can join its waitlist before you leave home. That's useful in its first weeks. The menu leans toward elevated pub fare, from artisan pizzas to Philly cheesesteak egg rolls. Marketing brand manager Stacy Erickson described the setting as a "laid-back tavern atmosphere" backed by "the heartfelt hospitality shared by our team."
Boardwalk Bar at Hotel Eastport is an indoor-outdoor bar just off the Boardwalk, open daily from 6 a.m. to 10 p.m. Happy hour runs 2 to 5 p.m. with $5 house wine, well drinks, Michelob Ultra and Yuengling. On Tuesdays at 5 p.m., the hotel's weekly events page lists a cocktail "Bar Ritual." Like Oak & Stone, the bar stays open until 10 p.m., matching the stage.
Yamas, the hotel's Greek restaurant, keeps different hours. Dinner runs 4 to 9 p.m. Monday through Thursday, 4 to 10 p.m. on Friday and Saturday, and 2 to 9 p.m. on Sunday. On a weeknight, the Yamas kitchen closes an hour before the band stops. Plan an early Greek dinner, then walk over for the last hour of music. If you'd rather keep eating until the band finishes, Oak & Stone is the better fit.
So the weeknight evening goes like this:
- The band starts at 6 p.m. Boardwalk Bar's happy hour has just ended at 5.
- Yamas serves dinner until 9 p.m., Monday through Thursday.
- From 9 to 10 p.m., Eastport has the only live music running at a Villages square, and both Oak & Stone and Boardwalk Bar stay open through it.
Tuesday, Oct. 6, puts it all on one night
If you only plan one October weeknight at Eastport, tomorrow has the most going on.
The day starts with Party in Pink Zumba at Center Stage from 9 to 10:30 a.m. In the evening, Hotel Eastport holds Oktoberfest at Boardwalk Bar from 5 to 8 p.m., with live music by Sandra & Alex. The menu includes warm pretzels with beer cheese, German potato salad, pork schnitzel with spätzle and braised red cabbage, brats with sauerkraut and roasted potatoes, and German cakes. The date isn't random. Boardwalk Bar has live music from 5 to 8 p.m. on the first Tuesday and third Thursday of every month, and Oct. 6 is the first Tuesday.
The Slickwood Trio plays Center Stage from 6 to 10 p.m. the same night. Oak & Stone's scheduled opening falls on the same date. A first-day restaurant is a moving target, so check its waitlist before you go.
The next Boardwalk Bar music night on that first-Tuesday, third-Thursday pattern is Thursday, Oct. 15. That evening Studio 77 plays Center Stage from 6 to 10 p.m., and Hula Ohana performs at 6:45.
The mornings belong to Sunset Island
The late nights are the headline, but Eastport's October calendar also uses the waterfront in the morning. A pedestrian bridge now crosses the water to Sunset Island. Villages-News describes the island as one of the square's best photo spots, along with the waterfront stage area, which looks out toward Hotel Eastport and the Welcome Center.
Sunset Island events still on the October calendar:
- Friday, Oct. 9: Karma Tai Chi & Qigong, 8 to 9 a.m.
- Thursday, Oct. 15: Phat Katz, 9 to 10:30 a.m.
- Thursday, Oct. 22: Bob Bartz, 11 a.m. to 12:30 p.m.
- Friday, Oct. 23: Karma Tai Chi & Qigong, 8 to 9 a.m., followed by Caleb Windham, 11 a.m. to 12:30 p.m.
For a full day at the square, Shooks Alley is a short walk from the waterfront. Its storefronts include Mia Sorella, Go Fish and The Villages Logo Store. Mia Sorella is owned and run by locals Sarah and Jimmy Cichielo. It carries Johnny Was, Southern Tide and Lilly Pulitzer for women, men and children, and it's open Monday through Saturday from 10 a.m. to 7 p.m. and Sunday from noon to 5 p.m. Saturdays on the October calendar are also marked "Shop & Dine Saturday," all day at the square.
The last stretch before the clock changes
October's final week brings Eastport's biggest events. Several of them spill over to the Farragut Softball Complex, not Center Stage.
- Saturday, Oct. 24. Thrill the World with the Thrillagers at 6 p.m. at Farragut Softball Complex. DeadLanders play Center Stage from 6 to 10 p.m.
- Thursday, Oct. 29. An outdoor screening of Hocus Pocus at Farragut Softball Complex at 5:30 p.m. Back at the square, CLUB CTRL featuring DJ Lu-S plays from 6 to 10 p.m., and Thrill The Villages performs at Center Stage at 6:45. This is also the last Thursday of the 10 p.m. weeknight window. You can see the movie and still catch the last stretch of music after it.
- Saturday, Oct. 31. Halloween night.
Halloween falls on a Saturday, so every square runs late that night. Each square also gets its own theme. Eastport's is "Icons & Idols," for costumes inspired by Hollywood legends, chart-topping musicians and pop culture figures. Blonde Ambition plays from 6 to 10 p.m., and the Thrillagers perform at 6:45. Eastport's contest has three categories:
- Ultimate Icon Award: best overall costume capturing an iconic figure
- The Headliners: best pair or group costume
- People's Choice: crowd-voted favorite of the night
Judges score costumes throughout the evening, and winners are announced at 8 p.m. at Center Stage. The featured cocktail at every square's bar huts that night is the Pumpkin Spike.
The Villages notes that all activities and times are subject to change without notice. The October calendar includes a QR code that links to the latest version, so check it before a night that depends on a specific act.
What's still behind the signage
Two more restaurants are visible from Eastport Drive but have no announced opening dates. Peach Valley Café is under construction at Eastport Drive and Dewey Drive, with "coming soon" signage and a hiring placard up. It's a breakfast, brunch and lunch concept. Tacos & Tequila Cantina is under construction next to Oak & Stone. Its original 2025 announcement said it would open "in 2026." If either opens before Nov. 1, it will be because of a date that hasn't been announced yet.
After Halloween, the schedule changes. Starting Nov. 1, Eastport's stage runs 5 to 9 p.m. like every other square, so the music starts an hour earlier and ends an hour earlier. Further out, Light Up The Villages is set for Dec. 1, 2026, at all Town Squares, with more details still to come.
Eastport's newest restaurant is opening right as its stage is in the last weeks of staying open later than anywhere else. If that has you wondering what your own home near the square would bring today, Martha Ridgway can give you a clear, honest number, along with practical advice on any repairs worth making first. Request Your Free Home Valuation.
