There are still plenty of things to discover in Winter Park and Maitland

Buttermilk Bakery
Buttermilk Bakery

The oldest incorporated town in Central Florida, Winter Park melds seamlessly with Orlando on one side, Maitland on the other, forming an amalgam of hipster hamlets and affluent areas. Winter Park’s getting her groove back, beyond all the bucks on display along Park Avenue and in Hannibal Square – and Maitland is getting in on the fun, as the 17-92 spine gets more built up every year. Joining the longtime anchor of Winter Park Village, there’s now the Lakeside Crossings restaurant complex across from the Trader Joe’s/Shake Shack shopping center; north of Lee Road the new Whole Foods Market and Nordstrom Rack have moved in across from the Ravaudage. But busy as it all is, there are still pockets of green quietude to be found.


The New General

155 New England Ave., Winter Park, 321-972-2819,

Tell that friend of yours who's always ordering from Brooklyn boutiques to quit trolling Instagram: She can find all the natural-leather clogs, small-batch skincare, handmade ceramics and boho linen clothing she needs here, plus a coffee and toast bar.

Nordstrom Rack

1090 N. Orlando Ave., Winter Park, 407-772-6010,

You know what Winter Park needed? Another place to buy expensive clothes. In all fairness, Rack, which opened on March 9 to lines out the door, is the brand's budget-friendly arm, the perfect spot to score discounted designer duds for all those summer weddings.

Skycraft Parts & Surplus

2245 W. Fairbanks Ave., Winter Park, 407-628-5634,

Weekend warriors, this is your place for nuts, bolts and all the sheet metal you can shake a PVC pipe at. Since 1974, this spot right off the I-4 Fairbanks exit has peddled yards of electrical wire, hardware and more. You know who also loves this place? Artists looking for a new medium.

Avalon Exchange

745 N. Orange Ave., Winter Park, 407-636-9304,

One of a chainlet of large resale stores somewhat akin to Crossroads or Beacon's Closet. The selection is vast – this is the kind of place where you leave with a garbage bag full of stuff if you're not careful. Bring in your oldies for store credit.

Atomic Junkies

1730 Fairbanks Ave., Winter Park, 321-439-9578,

Should you wish to furnish your home with sleek teak and geometric mid-century decor, this place is part furniture store, part art gallery. Atomic Junkies takes special care to find and restore rare pieces from the bygone designers of a simpler time.

Whole Foods Market

1030 N. Orlando Ave., Winter Park, 407-377-6040,

The new "Winter Park North" Whole Foods more than makes up for the parking woes Trader Joe's shoppers have dealt with for years now. Inside, there's a micro food hall, including custom wood-fired pizza, sushi counter, mochi freezer and juice bar. Plus, four rows of hot and cold bars for take-away.


Luke's Kitchen + Bar

640 S. Orlando Ave., Maitland, 407-674-2400,

Brandon McGlamery's bustling new Maitland boîte on the old Steak & Ale site had locals salivating in anticipation, and opening hasn't stemmed the flow one bit. Like McGlamery's other offspring, Luma on Park and Prato, Luke's sources seasonally and responsibly, but the approachable menu of "classic American cuisine" gets imaginative with dishes like snapper ceviche, rotisserie chicken and prime rib. 

KrungThep Tea Time

1051 W. Fairbanks Ave., Winter Park, 321-441-9598,

The inventive menu twists familiar Thai favorites into funhouse versions of themselves: tom yum goong soup becomes a snappy shrimp salad; gra-prow chicken finds itself in a grilled cheese sandwich with mozzarella and basil mayo; and iced teas are unicorn-hued.


125 N. Orlando Ave., 863-797-4233,

Jillian Hopke turns out cute cupcakes and fantastic fondant art at her shop on the shores of Lake Killarney. Flavors rotate daily, but a favorite is Cookie Butter, a nod to Trader Joe's next door.

Buttermilk Bakery

1198 N. Orange Ave., Winter Park, 321-422-4015,

Consider yourself challenged: Go have one of the gorgeous tartines at this tiny French-style modern bakery (we're partial to the mushroom and bechamel) and leave without one of those glistening pastries behind the counter. If you fail, which you probably will, a flaky kouign amann is a transcendent option.

Bulla Gastrobar

110 S. Orlando Ave., Winter Park, 321-214-6120,

Not exactly the ode to molecular gastronomy it promised to be, Bulla still puts out pretty good paella and top-notch tapas. You'll find Iberian musts like jamon Iberico and sangria, plus a lively scene for scoping out the Sunday-morning brunch crowd.

The Ravenous Pig

565 W. Fairbanks Ave., Winter Park, 407-628-2333,

Recent switcheroos in the Swine Family: Cask & Larder moved restaurant operations to the airport; the RavPig moved into that Fairbanks space (where C&L beer is still brewed), and Swine & Son Provisions next door just added Sunday service. Everything still tastes exquisite.

Hunger Street Tacos

2103 W. Fairbanks Ave., Winter Park, 321-444-6270,

Before Hunger Street Tacos, you could not find a squash blossom quesadilla in Orlando. After Hunger Street Tacos, that, and so much more. Also, it's the only place in town to find xocoflan, a "magical" chocolate cake topped with flan and caramel.


Foxtail Coffee

1282 N. Orange Ave., Winter Park, 407-951-7931,

True java aficionados will love the variety of fair-trade, single-origin coffees and variety of brew methods at this chic coffeehouse. If you just like joe, peruse the cute curios and people-watch, or grab the beanbags and play a few games of cornhole in the common area outside.

The Bear & Peacock

1288 N. Orange Ave., 407-801-2714,

Winter Park Distilling has been around for while, but their "brewstillery" is brand new. It's steps from Foxtail, so after you've hopped yourself up on caffeine, bring things down a notch with a tour and tasting of the beers and spirits made here, including Dog Island rums and Bear Gully whiskeys.

Deadly Sins Brewing

750 Jackson Ave., Winter Park, 407-900-8726,

Nestled into a former industrial space, the taproom retains a workmanlike atmosphere, with large roll-up doors open to the air during business hours. Devoted to providing variety, Deadly Sins offers styles of their own brew including Mango Habanero IPA, chocolate mint stout, coconut-infused cream ale and their neighborhood-repping 32789 Pale Ale.

The Geek Easy

inside A Comic Shop, 114 S. Semoran Blvd., Winter Park, 407-332-9636,

If the idea of a bar inside a comic-book store puzzles you, stop reading. If it sounds like the best thing ever, you're in for a lot of joy along with your Polyjuice Potion, Green Goblin cocktail and "I Am Groot!" veggie burger.

The Wine Barn

959 W. Fairbanks Ave., Winter Park, 407-599-9463,

Slake and bake at this misleadingly named wine shop (it's no barnyard), where you can sample bottles chosen from the enormous selection, or sit down for a wood-fired pizza.

The Porch

643 N. Orange Ave., Winter Park, 407-571-9101,

Sports bar with way-better-than-average food on the menu is a perfect place to catch the game, or just a hangover from the bottomless mimosas at brunch.


Blue Bamboo

1905 Kentucky Ave., Winter Park, 407-636-9951,

Recently emerging as one of Central Florida's premiere venues, this performing arts space is a sought-after spot to hear and see live music. It is all at once experimental music venue, recording studio, theater and art gallery. Grab a glass of pinot and settle in for a set.

Enzian Theater

1300 S. Orlando Ave., Maitland, 407-629-1088,

Our only arthouse cinema is home to the Florida Film Festival along with countless other mini-festivals and special screenings, as well as the magnificently pleasant Eden Bar.

The Alfond Inn

300 E. New England Ave., Winter Park, 407-998-8090,

Winter Park's newest boutique hotel also functions as an art gallery, hosting oft-changing selections from Rollins College's Alfond Collection of Contemporary Art. Have a drink in the lobby, tea in the salon, or a salad at in-house restaurant Hamilton's Kitchen; for those in the know, it's Winter Park's living room.

Central Park

West Morse Boulevard and Park Avenue, Winter Park

The green heart of Winter Park is an 11-acre park with fountains, a rose garden, public art installations, and seasonal events and festivals. No dogs allowed!