Winter Park is steeped in history everywhere you turn, from the Rollins College campus to greensward Central Park to the vibrant streets of historically Black neighborhood Hannibal Square. But it's also home to unbridled commerce: the most concentrated area of shopping that isn't a mall; the priciest real estate that isn't in Windermere or Isleworth; the trendiest sidewalk cafés. A sweet snack or frosty beverage is never more than a few steps away, the people-watching is premium and it's not difficult to while away a lazy Sunday at a bistro table. Park Ave has a distinctly European vibe, which isn't easy to find in Orlando. What it lacks in parking spaces (or drivers who are able to parallel park on the narrow, cobblestoned roads), Winter Park makes up for in trees: The city's urban forest consists of over 75,000 trees on private and public property.
HIGHLIGHTS
Farm + Haus Cafe, 526 S. Park Ave. Winter Park, 407-790-4371, farmandhaus.com
Like the East End Market original, local sourcing is of the utmost importance at the decidedly more upscale Park Avenue outpost of Patrick and Brittany Walsh Lyne's breakfast and lunch spot.
Park Avenue Tavern, 558 W. New England Ave., Winter Park, 321-972-1469, parkavenuetavern.com
The old Dexter's space in Hannibal Square got a much-needed refresh when this Manhattan import moved in.
Doshi, 1040 N. Orlando Ave., Winter Park, 407-571-9264, doshiorlando.com
The restaurant comprises a six-seat chef's counter plus a modern dining room where à la carte options of reimagined Hanguk cuisine go beyond gochujang drizzles and kimchi ornamentation.
Ava Mediterraegean, 290 S. Park Ave., Winter Park, 407-794-9896, avamediterraegean.com
The trendy room is saturated in SoBe swank, but the menu packs real substance. Don't miss the potato mille-feuille — it will remind you why you go out to eat instead of cooking for yourself.
The Courtesy, 1288 N. Orange Ave., Winter Park, no phone, thecourtesybar.com
Swine and Sons, 1280 N. Orange Ave., Winter Park, 407-636-7601, swineandsons.com
Orlando's OG craft cocktail bar relocated to the repurposed, industrial-chic State Auto Building, where it was shortly joined by Swine & Sons' stellar Southern fare and charcuterie.
Forward/Slash, 650 S. Capen Ave., Winter Park, no phone, drinkforwardslash.com
In addition to making premium blended whiskey, the high-end distillery features a tasting room and full cocktail bar and offers 90-minute, hands-on whiskey tasting experiences.
Austin's Coffee, 29 W. Fairbanks Ave., Winter Park, 407-975-3364, austinscoffee.com
Drink coffee or sip a beer and catch Orlando's local talent, with live music, comedy and poetry performances most every night.
Ravenous Pig Beer Garden, 565 W. Fairbanks Ave., Winter Park, 407-628-2333, theravenouspig.com
An open space that's a bit more casual than the dining room inside, where you can enjoy a beer brewed on-site along with the exquisite gastropub fare the Pig is known for.
Buttermilk Bakery, 1198 N. Orange Ave., Winter Park, 321-422-4015, buttermilk-bakery.com
The most delicious baked goods, but they sell out quick, so get up early. Worth it.
Winter Park Village, 510 Orlando Ave, Winter Park, 407-571-2700, shopwinterparkvillage.com
The shopping center is in the midst of a deep re-concepting, but as it evolves, you can still grab a Starbucks, shop at REI for your outdoorsy needs, or strum all the instruments at Guitar Center. The newly built Ruth's Chris is to die for.
New General, 155 E. New England Ave., Winter Park, 321-972-2819, newgeneral.us
Order coffee and food through takeout window, or hang out inside the cool, calm environs — and do a little shopping while you're there.
The Heavy, 1152 Harmon Ave., Winter Park, 407-489-8973, theheavywp.com
Not cheap, but absolutely gorgeous, plants, flowers and home decor. You'll want to hang out for a while, and hey, you can grab a coffee and do just that.
Blue Bamboo Center for the Arts, 1905 Kentucky Ave., Winter Park, 407-636-9951, bluebambooartcenter.com
Treasured local music venue keeps jazz-lovers entertained with everything from straight-ahead smooth stuff to more experimental skronk.
Rollins College, 1000 Holt Ave., Winter Park, 407-646-2000, rollins.edu
Yes, it's a private college, but it's also a public good: catch classical concerts by the Bach Festival Society, challenging art exhibitions at the Rollins Museum of Art, and a truly unique sonic experience on WPRK (91.5-FM), the student-run radio station.
SEE Eyewear, 342 S. Park Ave., Winter Park, 407-599-5455, seeeyewear.com
Cool-kid frames for those of us whose eyes don't work so good.
Writers Block Bookstore, 316 N. Park Ave., Winter Park, 407-335-4192, writersblockbookstore.com
One requirement of a civilized community is a bookstore, and this is Winter Park's.
Winter Park Train Station, 148 W. Morse Blvd., Winter Park, 800-872-7245
A picturesque stop for SunRail commuters and Amtrak travelers during the week, and a backdrop for the sprawling Winter Park Farmers Market on weekends.
Mead Botanical Garden, 1300 S. Denning Drive, Winter Park, 407-623-3342, meadgarden.org
A 48-acre oasis of flora and fauna open daily.
Winter Park Scenic Boat Tour, 312 E. Morse Blvd., Winter Park, 407-644-4056, scenicboattours.com
Scenic tours of Winter Park's waterways traverses tiny canals to give you another view of the city. Rides launch hourly starting at 10 a.m.
Kraft Azalea Garden, 1365 Alabama Drive, Winter Park, 407-599-3334, cityofwinterpark.org
A popular wedding and photography spot, the secluded lakefront offers a gorgeous view of wildlife, boats, and really expensive houses just across the lake.
Winter Park Library, 1052 W. Morse Blvd., Winter Park, 407-623-3300, winterparklibrary.org
Designed by starchitect Sir David Adjaye, this temple of literature doubles as an event venue, plus it's right at the edge of Martin Luther King, Jr. Park, if you need to stroll and muse on your reading.
Winter Park Sidewalk Art Festival, Central Park, 328 N. Park Ave., Winter Park, 407-644-7207, wpsaf.org
The festival debuted in March 1960 and is now one of the nation's largest and most prestigious outdoor art festivals. Annual event, every spring.
Dinner on the Avenue, Park Avenue and Morse Boulevard, Winter Park, 407-599-3342, cityofwinterpark.org
Want to keep those fancy Winter Park restaurateurs on their toes? Show them what you can do at this annual event, where attendees get creative with their own table setups. Bring a potluck dinner or hire a local caterer. Awards are given for best tablescape.
