The Village of Wellington's fall calendar for the Amphitheater at 12100 Forest Hill Boulevard lists two free series. They share a lawn and a stage, but they run on different schedules and are built around different things. "Thursday Nights in Wellington" opens at 5 p.m. and is mostly a market with a band on stage. The "Weekend Concert Series" opens at 6 p.m., and the headliner doesn't play until 7:30. Which one you pick decides what kind of evening you get, and from October 15 to October 17 you can try all three nights in a row.
Thursday is a market with a stage attached
The Village's event page lists the Thursday format as "Food Trucks | Live Music | Unique Vendors," in that order. The order fits. The page counts roughly 18 food trucks and 35 local small business vendors each week, and the shopping is billed as a Local Market tied to the Wellington Lakeside Market. Vendors sell handmade goods, baked items, specialty foods and gifts from 5 to 9 p.m.
The band doesn't start until 6:30, so the first 90 minutes are all food and browsing. The truck lineup changes weekly, and the Village posts each week's roster on its recreation Facebook account, @wellingtonflrec. The page also asks guests to bring their own blankets or chairs.
Through the fall, Thursdays also double as a drop-off for the Village's Holiday Food and Toy Drives. Non-perishable food is collected through Friday, November 13, and new, unwrapped toys through Friday, December 11.
The weekend series puts the show first
The Weekend Concert Series pages are organized around the performer. The Tito Puente Jr. page lists the Latin jazz set from 7:30 to 10 p.m. and food trucks from 6 to 10 p.m. Entry is free. The Turn It On Again page also lists a 7:30 start, with trucks winding down at 9:30.
The weekend pages don't mention the 35-vendor market, and they don't repeat Thursday's note about bringing chairs. None of the event pages we checked, Thursday or weekend, spells out rules on coolers, pets, alcohol or parking. The Village's general number for questions is (561) 753-2484.
Here are the two formats side by side, based on the Village's October listings:
| Thursday Nights in Wellington | Weekend Concert Series | |
|---|---|---|
| Gates and food | 5 to 9 p.m. | 6 p.m., trucks until 9:30 or 10 |
| Music starts | 6:30 p.m. | 7:30 p.m. |
| Market vendors | About 35 local vendors | Not listed |
| Food trucks | About 18, lineup changes weekly | Listed on each event page |
| Seating note | Bring blankets or chairs | Not stated |
| Cost | Free | Free |
That hour of difference adds up. On a Thursday, a family can eat, shop and catch the first set before a school-night bedtime. On a Friday or Saturday, most of the evening is the concert.
This is a returning fall rhythm under a new name
Weekend concerts at the Amphitheater aren't new. The Village's October 2025 calendar listed free shows on Friday, October 10, Saturday, October 11, and Saturday, October 18. Back then they were labeled "Free Concert," and they ran alongside a separately named Thursday Food Truck & Music Series.
The 2026 version has a brand of its own. By September 19, the Village was titling Saturday shows "Weekend Concert Series" and describing them as the "Fall Concert Series at the Amphitheater." Over the summer, the Town-Crier covered two free August tribute shows and reported that the Village was expanding entertainment opportunities for families. The fall calendar follows through on that, with two named series each holding its own nights.
The schedule can still change. The Village marked its October 1 Thursday show, Legends of Rock Horns / Brass Evolution, as "Canceled," and the event page gives no reason. The Village posts event and weather updates through the free Statusfy app and its Weather Field & Event Status page.
October 15 to 17 runs three nights in a row, and Saturday overlaps the Fall Festival
For most of the fall, the two series alternate. Mid-October is the exception. Three free Amphitheater nights fall back to back, and the last one lands on the same evening as the biggest family event on the Village's fall calendar.
- Thursday, October 15. Thursday Nights with Sugar Music Latin Band at 6:30 p.m. The market and food trucks run 5 to 9 p.m.
- Friday, October 16. Tito Puente Jr. plays Latin jazz from 7:30 p.m. This is also the last day for advance Fall Festival bracelet prices.
- Saturday, October 17. Hotter Than July, a Stevie Wonder tribute, at the Amphitheater from 6 to 10 p.m. The same day, Wellington's Annual Fall Festival runs 3 to 10 p.m. at Village Park, 11700 Pierson Road.
The festival opens three hours before the Amphitheater's 6 p.m. start that evening. The Village says the 3 p.m. start gives "families with younger children plenty of time to enjoy the festivities, while still getting their little ghouls and goblins home in time for bed." The festival lineup includes the one-night-only Haunted Hallways, hayrides, laser tag, a petting zoo, a pie-eating contest, costume contests, and trick-or-treating while supplies last, so bring a bag. New this year is Dryvebox Mobile Golf & Games.
Entry is free, but you need an all-access bracelet for the activities. The Village lists advance bracelet prices through October 16 at $7 for children and $5 for adults. The start times allow both events in one day, as long as you plan the order: Village Park in the afternoon, then the Amphitheater for the Stevie Wonder tribute.
The rest of the fall calendar
After mid-October, the two series go back to alternating, and other Village events fill the gaps.
- October 22: National Night Out with PBSO at the Amphitheater, 6 to 9 p.m.
- October 24: Turn It On Again, a Phil Collins experience, Weekend Concert Series.
- October 29: Ticket to the Moon, an Electric Light Orchestra tribute, Thursday Nights at 6:30 p.m.
- November 1: Wellington's 5K, 10-Miler & Tower Challenge, 7 a.m. at Tiger Shark Cove, 13800 Greenbriar Boulevard.
- November 5: The Derek Mack Band, Thursday Nights.
- November 7: "The Mystery Behind the Magic," a dinner-and-mentalism evening at the Wellington Community Center, 12150 Forest Hill Boulevard, 6 to 9 p.m. Tickets are $60, and childcare is available for ages 5 to 12.
- November 8: Wellington Rotary Ruck March & Food Drive, 8:30 a.m. at Village Park.
- November 11: Veterans Day Parade & Ceremony, 8:15 a.m. at the Veterans Memorial, South Shore and Forest Hill boulevards.
- November 12: Magic Ann, a Heart tribute, Thursday Nights.
- November 14: The Long Run, an Eagles tribute, Weekend Concert Series, 6 to 9:30 p.m.
- November 19: Vinyl Highway, Thursday Nights.
- November 21: Love Cats, a Cure tribute, Weekend Concert Series, 6 to 9:30 p.m.
November 13 is the last day for food donations, so the November 12 Thursday is the last market night where you can drop off food. Toy donations continue into December.
For a sit-down meal instead of the trucks, Molé Cantina at 2557 S. State Road 7, Suite 150, has new owners, Sia Hemmati and Chef Daryn Garcia, and a refreshed menu. The Town-Crier reported the change ahead of a public launch on October 6.
At Thalia & Kassandra, we keep track of Wellington's calendar the same way we keep track of its streets, down to which nights open at 5 and which at 6, and which neighborhoods are an easy walk or a short drive from Forest Hill Boulevard. If you'd like to talk about a home near the Amphitheater or anywhere else in the Village, schedule a free consultation and we'll walk you through it.
