Like all idylls, real “small town America” is nothing like Disney’s Main Street USA. The few places left in the country that have remained in their original incarnation have a seed-and-feed where the farmers purchase grain and equipment, a hardware store, a small grocers, a Five-and-Dime (such as Woolworths), and a bar. And that’s about it. No real ‘tourist appeal’ at all. But, although a genuine version doesn’t really exist in Central Florida, there are places that fit the myth, IF you stick to the high street area. It isn’t the Disney-inspired town of Celebration, but it is definitely worth a day trip.
WINTER PARK is a posh neighbourhood just north of downtown Orlando, with an overall atmosphere that feels both European and Floridian. Massive live oaks along the main strip of Park Avenue drip with silvery strands of Spanish moss, the street is made of cobblestones, and not only are dogs welcome at the outdoor cafes, most businesses have water bowls at their doorstep to keep Fluffy hydrated.
You don’t need an enormous bank account to visit (though we’ll admit it helps, because you’re going to shop and dine!), and you don’t have to dress up (though we admit there is an element of fashion-show about it, with some of the fashion being of the jogging suit variety). What you do need is a day—or half a day—and a car (or you can use the Sunrail system Mon-Fri).
Taking A Tour:
Pick up (or download) the free self-guided Walking Tour, with 20 stops around the historic downtown. Each stop on the tour includes little snippets of historical information, from the first building in Winter Park to charming Knowles Cottage, built with Florida’s original “snow birds” in mind. It’s a compact itinerary, and more an excuse for a nice walk than an in-depth exploration of local background.
Easier, and immensely enjoyable, is the Winter Park Scenic Boat Tour, which runs year round (not Christmas day) on Lake Osceola, just 3 blocks off of Park Avenue. The one-hour tour passes some of Winter Park’s most exclusive homes and through two picturesque canals, where shorebirds are common, gators are seen occasionally, and the locals are often out kayaking, with their dogs along for the ride. Take note, the boat ride is cash or cheque only. But don’t worry; it’s only $14 for adults and $7 for children ages 2-11.
That “Something Different” Factor:
The pretty campus of Rollins College is located at the southern end of Park Avenue, and makes for a serene walk around landscaped grounds and past Spanish-Mediterranean buildings. Stroll along the Walk of Fame, composed of stones from the birthplace of influential individuals, enjoy the walkway along Lake Virginia, and visit the free onsite Cornell Fine Arts Museum. Built in 1885, Rollins is Florida’s oldest college.
The Morse Museum sits on the opposite end of Park Avenue, and it’s worth a visit even if you’re not a ‘museum person’. Why? Because its collection includes the largest number of Louis Comfort Tiffany glass, lamps, jewellery and windows, the spectacular Tiffany Chapel, an absolutely stunning interior created for the 1893 World’s Columbian Exposition, and Tiffany’s magnificent Daffodil Terrace, reconstructed inside the museum. Admission to the museum is just $6, with ages 12 and under free.
Boutique shopping is big in Winter Park, with many of the shops along the main strip being locally owned. All of them are interesting or quirky (we’re looking at you, Ancient Olive), some, like Lilly Pulitzer, Ten Thousand Villages and Williams-Sonoma, are mainstream, but a few really fit the small town America theme.
Borders, Barnes & Noble and Amazon have all ploughed through the literary universe, slashing and burning the family-owned book shops, but Writer’s Block Book Store survived, and thrives. And, would you believe, it still does author book signing events. Talk about a rare commodity!
There is no feed-and-seed in town, but The Doggie Door is the modern version—sort of. What sets it apart from the typical pet supply store are things like designer cookies for Fido, Massage Saturdays (the canine version) and a wine cellar in the back room if your doggie has done something you really, really, really need to forget. Like *shudder* the time Susan’s dog ate an entire stick of butter….
Be sure to stop in at Peterbrooke Chocolatier before you leave, because chocolate.
Where to Eat:
Park Avenue and its side streets boast more than 40 dining locations, and you’ll struggle to go wrong with nearly all of them. Of particular note are Luma on Park, Bosphorus Turkish Cuisine, Prato, 310 Park South and The Wine Room, but our vote goes to an obscure choice just 2 blocks off the main strip.
Hamilton’s Kitchen is located on East New England Ave inside the swank Alfond Inn, and we love it for its fresh Southern-with-a-twist menu (white cheddar-bacon scones or black garlic risotto, anyone?). Enjoy the elegant but casual indoor setting, or do what we do and sip wine like the star you are in the courtyard patio. Finish your meal with the Macallan 12yr Butterscotch Pudding or Southern Pecan Bread Pudding for the full luxury experience. Ask about the Alfond Inn’s art tour and be amazed at the treasures lining the hotel’s walls.
Sure, you can get a salad, sandwich, or breakfast at Swine & Sons, but we’re including it here for the chance to stock up on provisions to take back to your villa for an al fresco dinner by the pool. Pick up the fixin’s for a charcuterie and cheese platter; add some cheddar chive biscuits and pimento cheese ham jam, and don’t forget the Chocolate Peanut Butter Whoopie Pies for dessert. Now that’s eatin’! Swine & Sons even dips its toe in the yesteryear theme with its Root Beer Float, which is America’s childhood in a glass.
While you won’t find the humble Main Street USA of years-gone-by in Central Florida, Winter Park is a distant, but highly enjoyable, second.
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