A quick trip west on the 408 expressway is all it takes to be transported to a historic downtown swaying with live oaks and Spanish moss. This town of just 34,000 has some Orlandoans giving up city life for small-town swagger, and Winter Garden residents are all too happy to show them the ropes. This is a spot where creative minds meet and big ideas flourish.
Plant Street Market
426 W. Plant St., Winter Garden, 786-671-1748, plantstmarket.com
Literally, there's a butcher, a baker and a candlestick maker all in one spot. Among the 20 vendors, you'll find wood-fired pizzas from Michael's Ali, farm-to-table cuisine at Five Thymes Five, expertly rolled sushi at Jodo, artisan chocolates from David Ramirez Chocolates, and craft coffee at Axum Coffee – all within steps of each other, so you can get all your shopping done and have lunch at the same time. The market is open seven days a week, and gets five-deep on weekends.
Crooked Can Brewing
426 W. Plant St., Winter Garden, 407-395-9520, crookedcan.com
It's a classic case of chicken or egg – which came first, the brewery or the market? In this case, the creator and owner of Crooked Can Brewing wanted his brewpub to be the centerpiece for a market where food artisans could come together and share their talents. Grab a stool at the bar or a table outside and taste award-winning craft brews like Cloud Chaser wheat beer, Highstepper American IPA and Workaholic pale ale. Each bartender is cicerone-certified (like a sommelier for beer), so even if you're not a hophead, it's likely they'll find you something to sip. And yes, that silo outside is actually full of grain.
160 W. Plant St., Winter Garden, 407-877-4736, gardentheatre.org
After your day of shopping and sipping, get out of the heat and into the Garden Theatre for a film, a concert or a live staging of one of theater's best-loved shows. This year's season includes Into the Woods, Jesus Christ Superstar and Neil Simon's The Odd Couple.
Chef's Table at the Edgewater
99 W. Plant St., Winter Garden, 407-230-4837, chefstableattheedgewater.com
Feeling more "dinner" than "show"? At the Chef's Table in the historic Edgewater Hotel, Kevin and Laurie Tarter offer an exquisite tasting menu (reservations required) or casual-but-upscale bites in their Tasting Room.