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Walking & Driving Tours

Quaint Winter Park, FL: Shopping and Tiffany Glass

Off the Theme Park Path:

Quiet Rambles in Winter Park, FL

Photo of Winter Park shops goes here.

By David Wilkening

Everyone’s heard of Orlando, king of the theme parks, but Winter Park? This small suburb just five miles north of Orlando is said to have 28,000 residents and 20,000 oak trees.

Yet despite its low-key aura, this “burb” has its own trendy claim to fame: Park Avenue (407-644-8281 or www.parkave-winterpark.com, 507 N. New York Ave. Shown at right, Park Avenue fields an incredible array of shops.*

This year-round shopping street destination is often compared to Rodeo Drive. You’ll find all the glitz but a more low-key, down-home feel. Don't expect Paris Hilton, Posh Spice or Beyonce ambling down the main street.

Do expect world-class shopping. About 140 shops occupy a 10-block area in the midst of a quaint town. Shops and boutiques include the well-known national brands. 

But visitors – with eclectic interests ranging from art to gourmet cooking and old books – will also find a tasty eclectic collection of more intimate, one-of-a-kind shops.

Perhaps the best part of a walking visit here, though, is that there’s plenty to explore without buying anything at all.

Walking Tour Brochure

Photo of Park Avenue goes here.Begin your tour with a stop at the Winter Park Chamber of Commerce to pick up a free historic Downtown Winter Park Walking Tour brochure and map (407-644-8281 or www.winterpark.org, 507 N. New York Ave.).

Or, you might just amble out for your own adventure. Tree-shaded, wide sidewalks (as seen at left*) allow people to walk side-by-side.

As you begin walking the smooth sidewalks, one of the first stores you’ll encounter is one of the most unusual: Downeast (407-645-5100), 538 South Park Ave.

At this store, the number one seller is Bill's Khakis, a men’s line of pants that was designed by a former military man dissatisfied with what was available in the marketplace, says owner Don Sexton.

Tool art goes here.In the old days, Park Avenue’s anomaly among the trendy shops was a Cottrell’s “five and dime” store. That’s long gone, and these days you’re more likely to be shopping at Restoration Hardware (407-622-1050 or www.restorationhardware.com), 400 Park Ave. South.

Here you can find just about anything – from a Grundig hand-cranked radio to kid’s snowshoes. The 11-drawer dressers go for $4,000 or so.

For a break, stop at Starbucks (407-599-4126 or www.starbucks.com), 400 Park Ave. South. You can pick up a copy of The New York Times any day of the week. But instead of coffee, try a Choi Tea Latte Grande for $3.35.

Women might want to stop at one of the various spas and beauty shops along Park Avenue, but men might prefer the more masculine Carr’s Barber Shop (407-628-8445 or www.carrsbarbers.com, 346 S. Park Ave.).

The slogan on Carr’s window is: “Between the cradle and the grave lies a haircut and a shave.” No appointment is necessary if you want to stop for a trim.

If it’s lunch or dinner time, most restaurants here can be recommended. Locals enjoy The Briarpatch (407-628-8651), 252 N. Park Ave. Opt for something unique; the $8.50 omelette including pears and gorgonzola is a unusual choice you won't find elsewhere. 

Perhaps the best spot overall for gourmet quality at a reasonable price is 310 Park South (407-647-7277 or www.310parksouth.net) 310 Park Ave. South. If it’s sunny, you can dine outside and order half a roasted duck served with a brandy demi sauce; the price is about $20.

Another option at $14 is the chicken roulade, a boneless chicken breast stuffed with spinach, gorgonzola cheese and roasted peppers, served with a brandy sauce.

In addition, a dozen or so sandwiches and hamburgers are priced under $10. Wash down your savory meal with any of 22 different beers.

Photo of shoppers along Park Avenue goes here.If you feel like sending someone a card, the Red Marq (407-647-2336), 308 South Park Ave., has the funniest and wittiest cards you’re likely to find anywhere.

Taylor’s Pharmacy (407-644-1025), 306 South Park Ave., next door is the oldest drugstore in the city.

Bringing a dog? You’ll notice that many stores have pet-friendly water bowls outside their entrances.

To get a flavor of the area, stop to look in the window of one of the local real estate offices.  Among them is the Winter Park Land Company (407-644-2900 or www.winterparkland.com), 122 South Park Ave. Above, visitors stroll a Park Avenue sidewalk in front of the land company.*

It's fun to window shop and a lot cheaper than buying! A dozen or so photos of homes are on display. What's interesting is that very few of the homes, even the tiniest ones, are priced at less than a half million dollars.

Book lovers undoubtedly will savor browsing at Brandywine’s Books (407-644-1711 or www.brandywines.com), 114 South Park Ave. At any point in time, owner Evelyn Walter Petit might sell anything from $1 used paperbacks to a $4,000 first edition of “Catcher in the Rye.”

If it’s time to rest your feet, you might sit on the benches shaded by large oak trees outside the St. Margaret Mary Catholic Church (407-647-3392 or www.stmargaretmary.org), 526 North Park Ave. If you admire church architecture, check out the handsome interior with a huge, vaulted ceiling.

Photo of a park goes here.New York aside, Park Avenue has its own identically named “Central Park” (407-599-3334 or www.wpcentralpark.com). The squirrel-rich area is only four blocks long.

But it features winding pathways and beautifully decorated gardens, such as the scene at right.*

You can also take in several pieces of sculpture here. The most imposing is the abstract work of Louise Nevelson’s “Night Gesture.” Visitors can ponder its meaning while listening to the more prosaic sound of train arrival and departure announcements coming from a loudspeaker at the nearby Amtrak Station.

Eventually, Park Avenue runs out of stores. But if you keep walking two more blocks, you’ll come to the Winter Park Golf Course (407-599-3339), 761 Old New England Ave.

The course is only nine holes, and it has no water. But it is historic. This is where many local residents -- kids and adults alike -- learned to play the game.

Check out the rules stated outside the small clubhouse (sorry, only one mulligan is allowed). You’ll also find the greens fee is only $12. That’s definitely the biggest bargain around.

Photo of Tiffany glass goes here.The crowning jewel of downtown Winter Park for travelers is the world-class Charles Hosmer Morse Museum of American Art (407-645-5311 or www.morsemsum.org), 445 North Park Ave.

Visited by more than 55,000 people annually, the museum is known internationally for its collection of works by Louis Comfort Tiffany – said to be the most comprehensive collection in the world.

It’s most popular enduring draw is the Tiffany Chapel, a mini-church built for the 1893 World’s Columbia Exposition in Chicago. It so moved fair-goers that men tipped their hats.

The chapel with four pews contains reflective glass mosaic surfaces. Light is filtered through the intensely colored, leaded-glass windows. Looking up, visitors see a 1,000-pound chandelier in the shape of a huge cross.

Photo of Tiffany Chapel goes here.The windows of the chapel are perfect examples of Tiffany’s glass work. One window alone has more than 10,000 separate pieces of glass.

Judges at the Chicago Fair said: “The wonderful iridescence of the blue and green glass gives a depth to the whole coloring and a mystic glow of the greatest beauty.” 

Even more than a century later, that observation is still quite accurate; the stunning chapel is shown at right, but the photo truly does not do it justice.*

The Morse Museum is a must-see attraction if you're headed to Winter Park. Admission is quite reasonable at only $3 per person. But if you want to save the charge, you may visit for free on Fridays from 4 to 8 p.m.

From Tiffany glass to eclectic shops, from affordable greens to savory dining, Winter Park is a treasure trove of diversions for visitors. So if you’re “doing the theme parks” but want a quieter day to amble along picturesque streets, browse a slew of shops, and yet still soak up a bit of Florida’s past, head for this enclave just 15-20 minutes north of downtown Orlando. 

*David Wilkening is a former newspaperman who worked in Chicago, Detroit, Washington and Orlando. He is now a freelance writer who lives in Orlando. He primarily writes about travel and business real estate subjects

*Photos are owned, copyrighted and used courtesy of both the City of Winter Park, FL, and the Charles Hosmer Morse Museum of American Art. All rights reserved. Do not link to nor copy these photos. Thank you. 

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