This town near Orlando is brimming with quaint, walkable delights.
It makes a quaint home base for travels and adventures around Orlando.
For the history enthusiasts, you could book historic guided walking tours here.

Winter Garden, FL.Credit:Getty Images/Wirestock
Youll share the trail with joggers, skaters, and even pro cyclists training for their next distance race.
The West Orange trail connects Floridas coast-to-coast cycle path.
Meander the Farmers' Market
Shop at theWinter Garden Farmers Market on Saturdaysin the downtown pavilion.

Garden Theatre in Winter Garden, FL.Credit:Courtesy of Garden Theatre
Dont leave without securing a souvenir from theA.B.
Newton & Companytent, a local print and design company famous for their regional city map prints.
The vintage-style theatre also hosts classic movie nights and touring productions.

Lee & Rick’s Oyster Bar.Credit:Courtesy Lee & Rick’s Oyster Bar
For a look at local visual art, stop inSoBo Art Galleryin the towns turn-of-the-century fire station.
The unadorned local haunt serves up fresh oysters and has a loyal following of local regulars.
This intimate restaurant offers a three-course prix-fixe menu that changes regularly, featuring the fresh Florida seasonal ingredients.

Oakland Manor House.Credit:Courtesy Oakland Manor House
No visit to Winter Garden is complete without a stop atCrooked Can Brewing Companywithin thePlant Street Market.
The bed-and-breakfast maintains its historic ambience with tasteful period decor.
The screened, wraparound porch is shaded in Spanish Moss and steps from Lake Apopka.
oaklandmanorhouse.com, 620 N Tubb St, Oakland, FL 34760