While leaves may not be falling, we are getting our first glimpse of temperatures falling! We are headed into one of our favorite times of year to enjoy beautiful Central Florida weather. And there is no better way than getting outdoors to enjoy music, food, shopping, and more.
Central Florida has so much to offer residents and visitors. Here's a look at just a handful of our top picks for Fall 2026.
Leesburg and Clermont Area Events - From Festival to Farm Fun
Discover Leesburg Second Friday
Location: Towne Square and downtown Leesburg
Date and Time: Friday, October 9, 2026, 6:00-9:00 p.m.
Admission: Free Admission
Downtown Leesburg comes alive with live acoustic music, an evening market, local shopping, and plenty of places to eat and drink. The relaxed, walkable setting makes this a strong choice for anyone who enjoys local music, small businesses, and an easy night out close to home.
More information: Discover Leesburg Second Friday
October Wine Stroll
Location: Downtown Clermont; check-in at The Art Walk, 756 W. Montrose Street
Date and time: Saturday, October 17, 2026, 6:30-9:00 p.m. (In-person check-in begins at 5:30 p.m.)
Admission: $25 Tickets; photo ID required
At this monthly event, guests receive a wine glass and map, then stroll through downtown while sampling red, white, and rose wines at more than 20 participating businesses. It is a particularly good fit for a 55-plus audience because it combines wine tasting, shopping, dining, and a leisurely downtown walk. Tickets are available online and in-person.
More information: Clermont Wine Stroll
Southern Hill Farms Fall Festival
Location: Southern Hill Farms, 16651 Schofield Road, Clermont
Dates: September 26-November 22, 2026, Thursdays and every Friday-Sunday
Times: Thursdays 11:00 a.m.-7:00 p.m.; Fridays 11:00 a.m.-8:00 p.m.; Saturdays 9:00 a.m.-8:00
p.m.; Sundays 9:00 a.m.-7:00 p.m.
Admission: Advance online ticket required
Adults can still enjoy this one, but you'll also want to grab your kids and/or grandkids if you got 'em! This large farm festival offers live music, wagon rides, a corn maze, u-pick flowers, pumpkins, petting zoo, seasonal photo spots, food trucks, and don't miss the apple cider donuts. Adults can also enjoy craft beer, wine, mimosas, a rooftop deck, covered seating, and the farm market, making it much more than a children's outing.
More information: Southern Hill Farms Fall Festival
2026 Fall Festival and Plant Sale
Location: UF/IFAS Extension, Discovery Gardens, 1951 Woodlea Road, Tavares
Date and time: Saturday and Sunday, October 10-11, 2026, 9:00 a.m.-3:00 p.m. daily
Admission: Free admission
Garden lovers can shop seasonal plants while exploring Discovery Gardens and learning from UF/IFAS horticulture experts. The free two-day event is an excellent choice for readers interested in gardening, Florida-friendly landscapes, local agriculture, and a pleasant daytime outing.
More information: Discovery Gardens Fall Festival and Plant Sale
Clermont Harvest Festival
Location: Downtown Clermont, 752 W. Montrose Street
Date and time: Saturday, October 31, 2026, 10:00 a.m.-4:00 p.m.
Admission: Free community festival
More than 100 artisan vendors fill downtown Clermont alongside live music and food trucks. The daytime schedule and abundance of handmade goods make it appealing for shoppers, while the costume contest for people and pets adds lighthearted fall fun.
More information: Clermont Harvest Festival
Ocala Area Events - From Music to the Arts
Dueling Pianos
Location: Midgett Black Box at the Reilly Arts Center, 500 NE 9th Street, Ocala
Date and time: Friday, September 25, 2026, 6:00 p.m.
Admission: Tickets listed at $33-$43
Two pianists lead an upbeat evening of soft-rock and pop favorites spanning decades, with cocktails and classic sing-alongs in an intimate cafe-table setting. The familiar music and social atmosphere make this one of the strongest entertainment choices for the newsletter's 55-plus readers.
More information: Dueling Pianos
59th Annual Ocala Fine Arts Festival
Location: Historic downtown Ocala
Date and time: Saturday and Sunday, October 24-25, 2026, 10:00 a.m.-5:00 p.m. daily
Admission: Free admission
More than 140 artists gather in downtown Ocala for one of the area's signature cultural weekends, with original artwork, live music, and entertainment. Complimentary admission, nearby restaurants, and a walkable downtown make this an easy all-day or half-day outing.
More information: Ocala Fine Arts Festival
Kissimmee and Celebration Area Events - From Barktoberfest to Roctoberfest
Barktoberfest - Dog Swim Event
Location: Bob Makinson Aquatic Center, 2204 Denn John Lane, Kissimmee
Date and time: Saturday, October 10, 2026, 1:00-4:00 p.m.
Admission: $5 per dog
This one is for your pup! We just couldn't resist including one for our furry friends. Kissimmee's Parks & Rec department is providing this dog-swimming event at the Bob Makinson Aquatic Center. Goes without saying this is only for the friendly, fun-loving types! (Aggression checks will be conducted at the door and owners are required to provide proof of current rabies vaccination.)
More information: Barktoberfest - Dog Swim Event
Rocktoberfest in Celebration
Location: Celebration Town Center, 701 Front Street
Date and time: Friday, October 16, 2026, 5:30-9:30 p.m., and Saturday, October 17, 2026, 5:00-10:00 p.m.
Admission: Free admission
Celebration's picturesque Town Center hosts two evenings of live music, German beer, bratwurst, pretzels, polka, seasonal treats, vendors, and stein-holding competitions. The walkable lakeside setting, dining options, and free admission make it a lively but accessible fall destination near Kissimmee and Solivita.
More information: Rocktoberfest (Friday) and Rocktoberfest (Saturday)
