One of the nicest things about many neighborhoods in larger, older metros (say, Chicago or Boston, for example) is their walkability. Ditching your car not only makes for fresh air and exercise, it makes a huge difference in how travel is experienced. Walking, window shopping, stopping for an impromptu coffee and sipping it on a sidewalk bench while the world moves past makes for true city immersion. It’s more genuine.
Of course, Orlando is newer – but it, too, has its enclaves, its history and its real “neighborhoods” in the more traditional sense of the word. And Winter Park – a city in its own right – is one of them. Begin your day early on Park Avenue with breakfast at the Briarpatch Restaurant. Cozy and quaint and well known for its various Benedicts and scrumptious pancake platters (try the raspberry lemon cream) along with traditional offerings and Southern yummies like fried green tomatoes, the Briarpatch has several al fresco tables that can’t be beat if the weather’s right.
A Briarpatch breakfast beneath the oaks. — Photo courtesy of Park Avenue, Winter Park
Feel free to chow down, because once the check’s paid you can (pretend it’s biologically possible to) walk it off and head south on Park Ave. eyeballing the shops as you go. Familiar names like Talbot’s, Lucky Brand and Lily Pulitzer share space with local offerings unique to the area, places like the Doggie Door, where pet lovers – four-legged friends often in tow – can find gifts for dogs, cats and people, from collars to pet-centric art, gourmet gifts to home furnishings. Make your way over to New England Ave. and take a right, passing verdant and flowery Central Park along the way. You’re heading into the Hannibal Square historic district.
The Doggie Door welcomes four- and two-legged shoppers. — Photo courtesy of The Doggie Door
Like Park Avenue, W. New England offers much in the way of scenic architecture, quaint cobbled roads and stylish salons, boutiques and eateries – Chez Vincent and Dexter’s among them – culminating in the beautiful and aptly-named Shady Park where live oaks tower and a refreshing splash pad makes a lovely break for the little ones you might have in tow. Come prepared with a quick change and a towel and grab some space on a bench while the kids cool off, then stroll on to check out the Hannibal Square Heritage Center.
Archival photography showcases neighborhood history at the Hannibal Square Heritage Center. — Photo courtesy of Hannibal Square Heritage Center
This free attraction chronicles the history of Hannibal Square via photographs, oral histories and more, telling the story of Winter Park’s “west side” and the African-American families who lived and worked here, playing an integral role in the growth and prosperity of the city. The Heritage Center also showcases permanent and visiting exhibitions and public art installations and plays host to myriad cultural events year round.
You’ll probably want lunch on your way back to fetch the car. Consider tapas at Mi Tomatina paella bar or a cheese-laden pie at Armando’s Pizzeria. You’ll pass both on your way back to Park Ave.