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Events

Winter Park Sidewalk Art Festival: go at opening, park far, walk in

Quick answerGo on the Friday or the first hour of Saturday, park a few blocks out and walk in. The festival is free, the art is good, and by midday on Saturday Park Avenue is close to gridlocked.
Good forArt lovers, couples, and anyone who likes a long stroll with good food stops.
Skip it ifYou hate crowds or need a stroller-friendly day on a busy weekend.
Cost check
WhatTypical
Entryfree
Parkingfree to about $20
Lunch on Park Avenue$15–$35 per person
Original artfrom small prints to thousands of dollars

When and where

The festival is usually held over a weekend in mid to late March, often the third weekend of the month. It has run since 1960 and is one of the longest-running outdoor art shows in the country. Booths line Central Park and the surrounding streets along Park Avenue in downtown Winter Park.

Expect a few hundred juried artists working in painting, photography, ceramics, jewelry, glass, sculpture and more. There's also a student and children's area, live music and food vendors. Entry is free.

Getting there and parking

Parking is the hard part. Lots near Park Avenue fill early, and side streets get packed. The simplest move is to park a mile out and walk, or get dropped off. Some churches, schools and businesses sell parking for the weekend, often at reasonable rates.

SunRail has a stop next to Central Park, which is ideal on days when the trains run. Weekend service has varied over the years, so check the schedule before you count on it. Rideshare drop-offs work well if you choose a pickup point a few blocks from the crowds.

How to see it well

  1. Arrive when booths open, usually around 9 a.m. The first hour is the calmest, and artists have time to talk.
  2. Walk the full loop once without buying anything, and note booth numbers you want to return to.
  3. Take a break around 11 a.m. before the lunch rush, either in the park's shade or at a café on a side street.
  4. Go back to your shortlist and buy. Many artists will hold pieces or ship them.
  5. Leave by early afternoon, or stay for a late lunch once the crowds start thinning.

Friday is usually quieter than Saturday. Sunday afternoon can be good too, though some artists start packing up near the end.

Buying art without regret

Artists here are juried, so the quality is high and so are some prices. That doesn't mean you have to spend big. Many booths carry smaller works, prints or cards alongside larger pieces, and those are the easiest way to take something home.

If a bigger piece catches your eye, take a photo of it and the booth number, then keep walking. If you're still thinking about it an hour later, go back. Ask whether the artist ships, since many do, and that saves you carrying a large frame through the crowd. Most booths take cards, but a little cash helps at the smaller ones.

Don't be shy about asking questions. Artists usually enjoy talking about their process, especially in the quieter morning hours. That's also when you'll hear about their studios or upcoming shows.

Eating nearby

Park Avenue restaurants fill up fast. If you want a sit-down lunch, book ahead or eat early. Side streets like New England Avenue and Morse Boulevard often have shorter waits. Our Park Avenue food guide lists options from coffee to full meals.

Food vendors in the park are easier, but lines build around noon. Coffee shops on Park Avenue are busiest first thing, so grab coffee on the way in or bring your own.

To make a day of it, the Winter Park Scenic Boat Tour leaves from the end of Morse Boulevard, a short walk away, and it's a calm hour on the lakes after a morning of crowds. Expect a line on festival weekends, so go early or late in the afternoon. The Morse Museum is also on Park Avenue if you want indoor time and air conditioning. Rollins College, at the south end of Park Avenue, has a pretty lakeside campus that's pleasant for a quiet walk when the festival gets loud.

Mistakes to avoid

  • Bringing a big stroller on Saturday. Walkways get tight.
  • Skipping sunscreen. Shade is patchy, and March sun is stronger than it feels.
  • Bringing a dog. Pets are usually not allowed, and the crowds are hard on them anyway.
  • Forgetting a bag. If you plan to buy prints or small pieces, bring something to carry them in.
If you only do one thingArrive at opening on Friday and walk the whole loop once.

Last checked November 2026. Hours, prices and schedules change; confirm with the venue before you go.

More postcards

  • Areas
    Winter Park

    Spend a morning in Winter Park: take the scenic boat tour, see the Tiffany chapel at the Morse Museum, then eat lunch on Park Avenue.

  • Eat
    Eating on Park Avenue, Winter Park

    Come for a long lunch or an early dinner, park once, and walk Park Avenue and Hannibal Square before choosing.

  • Free & outdoors
    The Winter Park Scenic Boat Tour

    Arrive before 10 a.m. or after 2 p.m. to avoid the longest wait, then ride the hour-long tour across three lakes and two old canals.