Winter Park is like Paris. If anything changes too much, the locals throw a hissy. It's a good thing most of the time; all the great stuff stays put, and all the not-so-great stuff sticks around long enough to see a rebirth. From the corner of Orange and Fairbanks to Aloma and Semoran's mammoth intersection, Winter Park's offerings are as diverse as its population.
GRAB A BITE
610 W. Morse Blvd., 407-843-2667, asouthernaffair.com
John Rivers' chicken place has taken root and there's a line out the doors most days for lunch, dinner and, most recently, breakfast. Dine on homemade Moon Pies, shrimp and grits, and of course, chicken and waffles.
Cask & Larder
565 W. Fairbanks Ave., 321-280-4200, caskandlarder.com
The other half of WP's restaurant royalty, James and Julie Petrakis, opened this temple of Southern cookery, canning and craft beer just down the road from their flagship, the Ravenous Pig. Look for their retail store, Swine & Sons, to open in spring of 2015.
223 W. Fairbanks Ave., 407-325-5165, scratchtapas.com
If you blink, you'll miss the tiny storefront on Fairbanks, but inside is a feast for the senses. Antique furniture, local art and seriously succulent small plates like pork belly adobo with black rice excite.
1945 Aloma Ave., 407-960-3922, igettoasted.com
A restaurant devoted solely to gourmet grilled cheese is as American as it gets, especially when the bread is slathered with butter, served extra crispy (with plenty of roasty burnt cheese bits) and paired with homemade tomato soup.
119 N. Orlando Ave., 321-203-5130, shakeshack.com
The New York chain has expanded worldwide and Orlando is officially cool enough to have one (or two; a second is soon to open on I-Drive). It's a cheat day place – you can't even get a burger on lettuce here – so go when you have the kcals to spend.
HAVE A DRINK
358 N. Park Ave., 407-636-7020
Opened atop Boca, the newest resident of the high-turnover space on Park and Canton, Park Social is a "speakeasy-style" bar (meaning you need a password to get in and its existence is not immediately apparent) with a swingin' 1970s vibe. Swill cocktails (both classic and original) and order the cheese plate.
480 N. Orlando Ave., 407-677-5000, tapsrestaurantbarandlounge.com
A huge beer list, wine on self-tap, a chic lounge space, tons of TVs – it's got everything for all people. Plenty of munchies, too, like nine different types of bruschetta and blue-kernel popcorn with truffle oil and grated Asiago cheese.
The Wine Room
270 S. Park Ave., 407-696-9463, thewineroomonline.com
You'll feel like you've stepped into a wine-obsessed yacht captain's study (ahoy!). More than 100 wines are available via machine dispenser, and each has a description so you can study up before you hit that "pour" button. Tasting pours start at about $2.
643 N. Orange Ave., 407-571-9101, winterparkporch.com
As the name suggests, most of this spot is outside, so it's best on clear days. Cocktails and beer are the focus here, but there is food available. Live music on Tuesday nights, brunch on Saturday and Sunday (the place has a mean Bloody Mary), and all-you-can-eat wings on Monday nights from 6-10 p.m.
CHECK THIS OUT
Scenic Boat Tour
312 E. Morse Ave., 407-644-4056, scenicboattours.com
Well worth your $12 (bring cash or write a check; no credit cards), this hour-long tour through the Winter Park chain of lakes is a sweet, Old-Florida way to spend an afternoon. Ogle cypress trees, scope for sorority girls sunbathing at Dinky Dock and spy on the wildlife.
Winter Park Sidewalk Art Festival
March 20-22, 328 N. Park Ave., 407-644-7207, wpsaf.org
More than 225 artists, photographers and artisans display their creations at this juried art festival in Central Park. Catch live music and entertainment throughout the festival, and pick up some new wall ornaments or one-of-a-kind jewelry.
Popcorn Flicks in the Park
251 S. Park Ave., 407-629-0054, enzian.org
Our local art house, Enzian Theater, partners with the city of Winter Park to present family-friendly films on the second Thursday of each month in Central Park. Bring a picnic (or a vat of ice cream from Kilwin's) and some blankets, and lounge on the lawn from 8 p.m. (weather permitting) till credits roll.
131 N. Orlando Ave., 407-622-0874, traderjoes.com
If you're coming to Winter Park from anywhere else in town, chances are you'll want to visit our only Trader Joe's (another is slated to open in early 2015 on Sand Lake Road in Dr. Phillips). Parking is tight, admittedly: Two Buck Chuck and cookie butter comes at a price.