Let this sink in: Eatonville is the oldest Black-owned municipality in the United States. Incorporated in 1887, it is the first town successfully established by African American freedmen. The significance of that fact may be belied by Eatonville’s small size and modest main street, but never, ever forget it. Eatonville can also boast of being the hometown of Harlem Renaissance literary titan Zora Neale Hurston, who wrote her best-known books in and about Eatonville, and whose body of work is celebrated every year at the annual Zora! Festival. And Maitland is entwined with Eatonville by more than simple geography — in the 1870s, as newly freed slaves sought to purchase land of their own, some settled around Lake Lily, then called St. John’s Hole, to work for northerners at their winter homes on the shores of Lake Maitland. Today Lake Lily is a posh little park surrounded by upscale restaurants. As you enjoy the annual Florida Film Festival, centered around the quaint arthouse cinema Enzian Theater, or explore the National Historic Landmark Maitland Art Center, never forget you tread on sacred ground.
HIGHLIGHTS
Kos, 449 S. Orlando Ave., Maitland, 801-518-6279, choosekos.com
Socially conscious Nordic coffee shop in Maitland serving from-scratch Norwegian waffles, Scandinavian open-faced toasts, skyr bowls and more.
DaJen Eats Café & Creamery, 323 E. Kennedy Blvd., Eatonville, 407-543-8105, dajeneats.com
Vegan Jamaican joint serves the breakfasts of your dreams, plus vegan “Irie Cream.”
Lazy Moon Pizza Maitland, 441 S. Orlando Ave., Maitland, lazymoonpizza.com
Pizza wars are heating up in Maitland — longtime local favorite and forever Best of Orlando winner Lazy Moon opens a third location here this summer, while new-school challenger Pizza Bruno plans to be serving Neapolitan pies in Maitland by late fall.
Soul Food Fantasy, 521 E. Kennedy Blvd., Eatonville, 321-972-3050, soulfoodfantasy.us
Braised oxtails, shrimp and grits, jerk turkey wings — your Southern kitchen fantasy comes to real life here.
Teak Neighborhood Grill, 901 S. Orlando Ave., Maitland, 407-335-4835, teakorlando.com
Burgers so big and bustling with toppings you might need a knife and fork.
Copper Rocket, 106 Lake Ave., Maitland, 407-853-5036, thecopperrocket.com
Longtime cozy beer pub hosts an excellent selection of open mics.
Enzian Theater and Eden Bar, 1300 S. Orlando Ave., Maitland, 407-629-1088, enzian.org
Sip a craft cocktail on one of the most romantic patios in Central Florida, before or after you head inside to catch a flick.
Outpost Kitchen, Bar & Provisions, 111 S. Orlando
Ave., Maitland, 407-930-6282, outpostkbp.com
“Boozy brunch” is spoken fluently here.
Zora Neale Hurston Museum of Fine Arts, 344 E. Kennedy Blvd., Eatonville, 407-647-3307, hurstonmuseum.org
Hub of the annual festival and host to works exclusively by Black artists.
The Moseley House, 11 Taylor St., Eatonville, 407-622-9382, themoseleyhouse.org
This historic museum is the second oldest structure in town. The house was owned by Matilda Clark Moseley, niece of Eatonville’s founder and first mayor.
Art & History Museums — Maitland, 231 W. Packwood Ave., Maitland, 407-539-2181, artandhistory.org
Truly one of the most beautiful museum campuses you’ll ever see, and a crucial incubator for boundary-pushing local talent. Wander the grounds, but don’t disturb the resident artists at work.
Audubon Center for Birds of Prey, 1101 Audubon Way, 407-644-0190, cbop.audubon.org
Ka-KAWWWR! You may hear the movies’ most famous sound effect, the cry of the red-tailed hawk, in real life if you visit this sanctuary for big-bird rehab.
Zora! Festival, annual in January, zorafestival.org
A multi-pronged, nearly monthlong affair ranging from scholarly lectures to Afrofuturist art exhibitions to a “ladies in hats” lunch, all culminating in a weekend fair of music, food and family fun.
Florida Film Festival, April 14-23, 2023, floridafilmfestival.com
Ten days and more than 160 films, plus first-class events where film lovers mingle with filmmakers and celebrities.
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Welcome to Orlando City Guide 2023
This article appears in City Guide 2023 and City Guide (2023).