Just minutes north of Orlando, discover seven reasons to fall in love with Winter Park, once an historic winter resort community and now a charming destination with enchanting museums, pristine parks, lakes and a walkable downtown.
Winter Park chain of lakes
Since Winter Park feels like a “world” away from the tourist corridor, it always surprises visitors that its location is just minutes away from the world’s most popular theme parks.
Winter Park was originally developed for wealthy Northerners seeking a tranquil place to live and escape from the harsh winters. Winter Park was actually called Lakeview until 1881 when two businessmen, Loring Chase and Oliver Chapman, decided they wanted the name to be more representative of a park in the winter … thus Winter Park was born. To this day, the city still attracts a lot of winter visitors because of its wonderful weather, relaxing lifestyle and plethora of unique places to visit.
Winter Park peacocks roam the streets
There are so many reasons to fall in love with this quaint city and it has been featured in numerous articles, movies and TV shows. National Geographic Traveler magazine recognized the city as one of the world’s top historic destinations, noting “this gracious town manages to retain its reputation as an oasis within the helter-skelter growth of Central Florida. Winter Park’s small downtown has a commercial district with some interesting historic buildings and small businesses. It also has a nice historic residential area. There is a clear sense that this is very much a place where people live, work, go to school – not just a showpiece for tourists.”
In 2015, Winter Park was also featured in an award-winning Super Bowl commercial. Winter Park was the selected location because it symbolized the quintessential American hometown.
Winter Park’s vision statement really sums up its essence: Winter Park is the city of arts and culture, cherishing its traditional scale and charm while building a healthy and sustainable future for all generations.
Here are a few of our favorite hot spots in Authentic Winter Park:
The Winter Park farmers’ market
The Winter Park Farmers’ Market is held every Saturday morning from 7 am to 1 pm and is a great motivator to get out of bed. Housed at an old train depot that is a restored historical landmark on the corner of W. New England Avenue and S. New York Avenue, it is a very popular community-gathering place.
Since it’s in Winter Park, you can expect to find a few upscale choices than you’d find at more typical farmers’ markets. The breakfast and lunch choices are stellar. Look for fresh crepes, pastries, and quiche. Buy the honey. There is also always a great plant selection. We found the prices tend to go down the closer you get to 1 pm.
There’s also an indoor vendor space, which is great when the weather is challenging. Within the same building is the Winter Park Historical Museum, which is open on Saturday from 9 am until 1 pm. Admission is free and exhibits put a historical focus on some of Winter Park’s traditions and events.
Please note: The Winter Park Farmers’ Market closes each year on the third Saturday in March because of the Winter Park Sidewalk Art Festival.
Check out even more of our favorite Farmers Markets across Florida here!
The Winter Park boat tours were established in 1938
Established in 1938, the fleet of six 18-passenger boats travels through the pristine Winter Park Chain of Lakes. It is a definite MUST SEE for locals and visitors alike. Every tour promises breathtaking views of nature as well as a historic overview of the luxurious private homes and estates along the shores. Keep an eye out for the occasional water skier, yogi on a paddleboard, or a sunbathing alligator.
The dock is less than a 5-minute walk from Park Avenue and is located on the East end of Morse Boulevard on Lake Osceola.
Admission is $14 for adults and $7 for children. Taxes are included (ages 2 through 11); Under 2 are free.
They only accept cash or checks! Operating hours are 10 am to 4 pm daily (except Christmas).
Rollins College is ranked as one of the most beautiful US college campuses
Founded in 1885, Rollins College is Florida’s oldest recognized college, and is consistently ranked by U.S. News & World Report as one of “America’s best colleges.”
The College of Arts & Sciences offers full-time undergraduate programs in the liberal arts. The Crummer Graduate School of Business is consistently ranked by Forbes magazine among the best business schools for return on investment, and Forbes recently ranked the MBA program No.1 overall in Florida. The Hamilton Holt School serves the Central Florida community by offering exceptional undergraduate and graduate degree programs during evenings and weekends to students diverse in age, experience, and professional development.
Rollins College has been ranked among the most beautiful U.S. college campuses by the Princeton Review for the past decade. They ranked #1 in 2015 and #10 most recently in 2017.
Boat basin, Rollins College
The Rollins 70-acre campus contains a range of amenities, including a theater for performing arts; the Cornell Campus Center; and also the Alfond Sports Center. Rollins also owns and operates a full-service hotel nearby called the Alfond Inn. We recommend this to anyone needing overnight accommodations.
Located on the banks of lovely Lake Virginia, it’s a great campus to informally walk around. If you want to set up a campus tour, contact the Office of Admission or also visit this link.
Charles Hosmer Morse Museum of American Art
Opened in 1995, The Charles Hosmer Morse Museum of American Art (“The Morse Museum”) houses the most comprehensive collection of works by American designer Louis Comfort Tiffany (1848–1933), including the chapel interior he designed for the 1893 World’s Columbian Exposition in Chicago and art and architectural elements from his Long Island estate, Laurelton Hall.
Highlights also the recently restored Daffodil Terrace, prize-winning leaded-glass windows, iconic Tiffany lamps, and custom furnishings are among the featured installations. Visitors will also enjoy the exhibits of American art pottery, Arts and Crafts furnishings, and late 19th- and early 20th-century American painting and graphics.
The Morse Museum is opened 9:30 am – 4 pm Tuesday through Saturday. (Open until 8:00 pm Friday, November through April) and 1 pm – 4 pm on Sundays. Closed Monday and most major holidays
Admission is $6 for adults, $5 for Seniors age 60 and older, and $1 for students (with valid ID). The museum is free for children younger than 12
All visitors free 4 pm – 8 pm on Fridays (November through April)
Albin Polasek Museum and Sculpture Garden
The Albin Polasek Museum and Sculpture Garden (“The Polasek”) in Winter Park is dedicated to promote the legacy of internationally known Czech-American sculptor, Albin Polasek. It also enriches lives through the power of inspiration conveyed by his story, setting and art.
The Polasek features over 200 works by Albin Polasek. In 2000, Albin Polasek was named a “Great Floridian” by the state of Florida, a distinction that recognizes those who made significant contributions to the history and culture of the state. In 2004, the Florida Artists Hall of Fame inducted Albin Polasek.
The Polasek is also on the National Register of Historic Places and National Trust of Historic Artists Homes/Studios. The Polasek hosts events such as the “Winter Park Paint Out” and is available for weddings and meeting rentals.
The Albin Polasek Museum & Sculpture Gardens is a 501(C)(3) public charity, non-profit organization whose budget is also funded by donations and membership. All donations and dues go to support its preservation, maintenance, and operation.
The Polasek is open Tuesday through Saturday from 10 am – 4 pm; Sunday from 1 pm – 4 pm. Admission is $5 for adults, $4 for Seniors (60+), $3 for Students (age 12 through college). Members and children under 12 are free.
Free Days include Heritage Day and also Veterans Day.
“Happy House”, also known as Casa Feliz is the beautifully restored Spanish Farmhouse designed by acclaimed architect James Gamble Rogers II. The exterior of the house and grounds are picture-perfect and an amazing place for weddings and other special events. The rich textures of original Spanish roof tiles and whitewashed century-old bricks, a turret, a bell tower, a heavy timber balcony detailed in colors of the Mediterranean, lush landscaping – courtyards, sweeping oaks, and also native plants – make it a must-see in Winter Park.
Casa Feliz is open to the public free of charge for self-guided tours on Tuesday and Thursday from 10 am – 12 pm. “Music at the Casa” also happens on Sundays from 12 pm – 3 pm. Private tours arranged by calling 407.628.8200.
Casa Feliz hosts special events for the public throughout the year and especially around the holidays. FYI: Santa Claus also always makes a pit stop at Casa Feliz.
Park Avenue Shopping District, Winter Park
One of the best ways to describe Park Avenue is new-world sophistication meets old-world charm. Park Avenue borders the crown jewel of all the city’s parks. An 11-acre park that boasts shady oak trees, landscaped planters, sitting areas, open space, and three beautiful fountains. There is even a rose garden at the southern corner of Central Park where you can take time to stop and smell the roses. The lush foliage and relaxing atmosphere also make it the perfect spot for a picnic.
Playing host to a variety of outdoor concerts, movie screenings and art festivals, Park Avenue is home to an array of unique boutiques and gift shops, world-renowned art museums, chic salons/spas and epicurean delights from sidewalk cafes and also trendy wine rooms to fine dining and gastro pubs.
Often called “Little Europe,” Park Avenue is a destination that has provided the citizens and visitors of Winter Park with an elegant place to stroll, dine, and also shop.
The official Park Avenue walking map is also a great tool to use. Grab a cup of coffee or an iced tea at Orlando’s favorite coffee spot, Barnie’s, and experience Park Avenue by foot.
Authentic Florida Trivia Question:
Where was the world-famous “temple” orange discovered? (FYI: The Temple is technically a hybrid known as a “tangor”, a cross between a tangerine and an orange.)
Answer: Winter Park!
About the Author: Melanie Lentz-Janney, the Chief Experience Officer of Authentic Florida Media, moved to Florida in the mid-1970s from New York City. As a blogger, she is devoted to discovering authentic Florida experiences and is a magnet when it comes to Florida Kitsch. You can connect with Melanie on LinkedIn.
AuthenticFlorida.com was named Best Travel Blog two-times at the Florida Sunshine Awards.
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