The Best Things to Do in Windermere
A Friday farmers market, a famous chain of lakes, 438 acres of preserve trails, a hometown brewery and a calendar of art shows — the best ways to spend a day in Orlando's quietest town.
3 minute read
Windermere does not do attractions the way the rest of Orlando does. There is no gate, no queue and no parking garage — just a lake town’s worth of genuinely good ways to spend a day, most of them free, nearly all of them outdoors. Here is the town’s best, in the order a local would stack them.
Start with Friday
The Windermere Farmers Market — No. 3 in our Orlando farmers market rankings with a Net Score of 90.0 — fills Town Square Park every Friday from 9 a.m. to 1:30 p.m. with produce, bread, homemade pasta, local honey and flowers, in front of the historic Town Hall. Build the morning around it: breakfast at Dixie Cream Cafe, coffee from Paloma Parlor, and a slow loop of the historic Main Street blocks while you are there.
Get on the water
The Butler Chain of Lakes is the main event. Thirteen clear, connected lakes surround the town, and R.D. Keene Park at 10900 Chase Road is the public way in — a 52-acre county park with soccer fields, a covered playground, picnic space and one of only two public boat ramps on the chain. Without a boat, take a captained cruise with Orlando Lake Tours from the same park: Bird Island’s protected rookery, the canal runs and the chain’s famous shoreline, all narrated. Bass anglers should book a guided trip; the chain’s largemouth reputation is earned.
Walk the wild side
On the town’s southern edge, Tibet-Butler Preserve protects 438 acres of pine flatwoods, cypress swamp and oak hammock along the Butler Chain’s shore. More than three miles of free trails loop through it, including boardwalks over the wetlands and the Osprey Overlook pavilion on the water. Start at the Vera Carter Environmental Center for the butterfly and pollinator garden, the live gopher tortoise exhibit and a trail map. Practical notes from the county: admission and parking are free, bicycles are not permitted on the trails, and pets are not allowed — the wildlife is the point, and it shows up accordingly. Trails can run muddy after rain, so wear shoes that can take it.
The porch, the park and the slow hours
Between the headliners, Windermere’s smaller pleasures fill a day out. The Windermere Branch library at 530 Main Street — a Florida Cracker-style building with a wraparound porch, steps from Town Square — is the town’s cool, quiet room on a hot afternoon, and its porch may be the best free seat in town. R.D. Keene Park doubles as the local sports ground, with rentable soccer fields and a big covered playground that makes it the default family picnic site even for visitors who never launch a boat. And the simplest Windermere experience costs nothing at all: a walk or slow drive along the sand streets under the oak canopy, past the 1880s schoolhouse and the old citrus grove, with Lake Butler winking through the trees. The town has protected that canopy and those unpaved streets by ordinance and by habit; walking them is walking through a decision the town keeps making.
Evenings and the calendar
Windermere after dark used to mean driving somewhere else. No longer: Windermere Brewing Company runs Tuesday trivia and Friday live music in its yard off Fifth Avenue, Fresco Pizzeria serves dinner on Main Street, and Solvino pours for the wine-minded. The town calendar adds the punctuation: the Windermere Fine Art Show at Town Hall each spring, a holiday art show on the square in November, and monthly food-truck nights that run into the evening. One more ranked stop for the list: Windermere Nails & Spa, at 4848 S. Apopka Vineland Road on the town’s eastern edge, holds No. 2 in our Orlando nail salon rankings with a Net Score of 97.4 — see the category winner’s story in our Tammy’s Nail Salon feature.
Every stop here is pinned on our Orlando Top Spots Map, and the Windermere hub collects the town’s full coverage. Come Friday if you can. Come slowly either way.
Photo: Ash Dunassyn, CC BY-SA, via Wikimedia Commons.
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