Soak in the sights and the history of Eatonville and Winter Park

Winter Park's Hannibal Square
Winter Park's Hannibal Square Photo via Visit Florida

Winter Park is a city steeped in history everywhere you turn, from the Rollins College campus to Central Park to the vibrant streets of historically Black neighborhood Hannibal Square. And, as the first Black incorporated municipality in Florida, nearby Eatonville has an independent streak going back to its very beginnings in the 1800s. Though College Park has the Kerouac House, Eatonville can boast of being the hometown of literary titan Zora Neale Hurston, site of the annual Zora! Festival and a cultural hub worth a visit any time of the year. Ritzy Winter Park and restaurant-heavy Maitland are prime destinations for locals wanting a quality meal, world-class museums and fancy shopping. All three neighborhoods always seem to have something new cooking.

Enzian Theater
1300 Orlando Ave., Maitland,

The arthouse cinema/bistro is open for business and pushing forward with screenings and some special programming like themed classics series and the Florida Film Festival. Pairing that with a robust campaign of streaming screenings and rentals of adventurous new fare is a canny move, too. The adjoining Eden Bar is a beautiful outdoors spot to enjoy a bite and a beverage.

click to enlarge Winter Park's Park Avenue - Photo by Barry Kirsch
Photo by Barry Kirsch
Winter Park's Park Avenue


It's been a turbulent couple of years for the best in basement radio and the voice of Rollins College. Repeated moves and temporary homes had finally come to an end with a move into a gorgeous state-of-the-art new studio ... and then the pandemic hit. The station is still plugging away, with hosts sending in their playlists remotely for the city to enjoy. So while it's not quite up to full, eclectic strength, it's still a relief to hear WPRK on the FM dial.

SkyCraft Parts & Surplus
2245 W. Fairbanks Ave., Winter Park,

Despite some chatter last year that they were moving, the Winter Park standby is open and ready to fill your needs for electronics, hardware, tools, circuitry and all manner of mad-scientist worthy gear you didn't even think you needed. Do your DIY repair shopping here.

click to enlarge Art & History Museums - Maitland
Art & History Museums - Maitland

BAMF Comics & Collectibles
500 E. Horatio Ave., Maitland,

Maitland comics and coffee clearinghouse par excellence is still continuing much the same as always – though they have shifted most of their innovative store events and programming online. The well-curated selection of comics new and old, gaming supplies and toys is continuously growing, and they are open for in-person shopping or curbside pickup.

Teak Neighborhood Grill
901 S. Orlando Ave., Maitland,

Maitland burger haven Teak has been getting a lot of televised attention lately: a segment of Food Paradise and a spot on Travel Channel's 50 States of Burgers. And now that the word's out on their second, "secret" menu, you have twice as many reasons to visit for some to-go dinner.

The New Standard
1035 Orlando Ave., Winter Park,

When it opened last year in the Ravaudage complex, the New Standard concert venue/eatery promised to set a, well, new standard for live music in the Orlando area with state-of-the-art sound and lights and a busy live music calendar. For now, the restaurant is still going strong, there's been a robust livestream schedule and it looks like some dinner shows are in the works. Also: lovely batch cocktails to go!

click to enlarge Knowles Chapel at Rollins College - Photo by Hannah Glogower
Photo by Hannah Glogower
Knowles Chapel at Rollins College

The Ravenous Pig
565 W. Fairbanks Ave., Winter Park,

With the June addition of new executive chef Clay Miller (formerly of Dovecote), the well-loved gastropub looks to be starting a new chapter, but still offering the same nouveau American cuisine and drinks, either in-person or to-go.

Winter Park Farmers' Market
Central Park West Meadow, New York Avenue and Morse Boulevard, Winter Park,

Being outdoors is where it's at these days, as is supporting local merchants, vendors and farmers. You can do both those things at this outdoor weekend market, and be assured of freshness of product and quality more than at a big box store.

Rifle Paper Co.
558 New England Ave., Winter Park,

This ground zero for an endless array of aesthetically pleasing stationery, cards, journals and more is definitely worth a visit. Plus now is a great time to actually start writing letters (in style) again. Recently Rifle was in the news for donating their fabric to Orlando Face Mask Strong to make masks for caregivers.

Soul Food Fantasy
521 E. Kennedy Blvd., Eatonville

Specializing in good old BBQ, seafood and Southern specialties, Soul Food Fantasy offers a variety of stellar comfort food for anyone with an appetite for home cooking.

DaJen Eats
323 E. Kennedy Blvd., Eatonville,

If you didn't think it was possible to enjoy the delicious island flavors of Jamaica in vegan dishes, DaJen Eats will prove you wrong. Owner Jenn Ross, a self-described "happy, irie vegan," impresses with a menu that includes chick'n and biscuits, vegan rice bowls, "hoax tails" and dairy-free ice cream.


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