A historic small-town main street about 28 miles west of Lake Nona, with restaurants, breweries, a restored theater, a Saturday market and a busy event calendar.
Historic downtown Winter Garden is about 28 driving miles west of Lake Nona Town Center. Its main street, Plant Street, is lined with restaurants, breweries, bars, shops and galleries. The West Orange Trail, a paved trail of about 20 miles for walking and biking, runs straight through downtown along Plant Street. The Winter Garden Farmers Market is held on Saturday mornings at the downtown pavilion. Downtown hosts free live music on Friday nights and a calendar of seasonal festivals and holiday events.
Downtown Winter Garden is a century-old citrus town's main street that has become one of the Orlando area's most popular places to eat and spend a Saturday. Plant Street has a restored 1930s theater, a food hall with a brewery, restaurants and bars, and a paved trail running down the middle of it.
This guide is for Lake Nona residents looking for a day trip. It covers how far downtown Winter Garden is and what to do there: the restaurants, entertainment and events.
How far is downtown Winter Garden from Lake Nona?
Downtown Winter Garden is about 28 driving miles west of Lake Nona Town Center.
The usual route takes SR 417 and Florida's Turnpike, both toll roads, to SR 50 and then local roads into downtown. It avoids I-4. Downtown has free public parking lots and street parking, which fill up on Saturday mornings and during events.
| Distance from Lake Nona Town Center | About 28 miles |
|---|---|
| Main street | Plant Street |
| Trail | West Orange Trail runs through downtown |
| Farmers market | Saturday mornings |
| Free live music | Friday nights at Centennial Plaza |
Where do you eat and drink in downtown Winter Garden?
Plant Street and the blocks around it have a dense mix of restaurants, breweries, cocktail bars and wine bars, and the Plant Street Market food hall is the easiest place to start.
Plant Street Market is an indoor market of food and drink vendors anchored by the Crooked Can Brewing Company, and it works well for a group that can't agree on one restaurant. Along Plant Street itself you will find sit-down restaurants, cafes, dessert shops and several bars, with outdoor seating along the trail. Restaurants come and go, so the downtown business directory is the best way to check what is open.
What entertainment is there in downtown Winter Garden?
The restored Garden Theatre, free Friday night music at Centennial Plaza, two small museums and an art gallery give downtown more to do than just eating.
- Garden Theatre: a restored 1930s theater on Plant Street that stages plays, musicals, concerts and film screenings.
- Fridays on the Plaza: free outdoor live music at the Centennial Plaza gazebo on Friday evenings.
- Winter Garden Heritage Museum and Central Florida Railroad Museum: two small downtown museums on the town's citrus and railroad history.
- SOBO Art Gallery: a local art gallery in downtown's historic former fire station.
When is the Winter Garden Farmers Market?
The Winter Garden Farmers Market is held on Saturday mornings at the downtown pavilion, a block off Plant Street.
It is one of the busiest markets in the Orlando area, with produce, baked goods, plants, prepared food and crafts. For a Lake Nona day trip, the classic plan is to arrive in the morning for the market, have lunch on Plant Street, and walk or bike a stretch of the trail. Arrive early, as parking fills quickly on market mornings.
What is the West Orange Trail?
The West Orange Trail is a paved walking and biking trail of about 20 miles that runs through the middle of downtown Winter Garden along Plant Street.
Downtown is one of the most popular starting points on the trail, and bike rentals are available nearby. Even a short ride out and back makes a good addition to a market morning or a lunch on Plant Street. Bring water in warmer months, as much of the trail is in the sun.
What events are held in downtown Winter Garden?
Downtown hosts events year-round, from weekly Friday music and the Saturday market to seasonal festivals and a busy holiday season.
Annual highlights usually include a spring festival, a music festival, Halloween events, and a holiday season with a tree lighting, a holiday market and the Winter Garden Christmas Parade. Event dates change each year, so check the downtown events calendar before you plan a trip around one.
Pros, Cons and Our Take
Pros
- A walkable historic main street with a wide choice of restaurants and bars.
- A Saturday farmers market and free Friday night music.
- The West Orange Trail runs right through downtown.
- A restored theater and small museums add more than dining.
Cons
- About 28 miles each way from Lake Nona, with tolls.
- Parking fills up on Saturday mornings and event days.
- Restaurants and bars turn over, so check what is open before you go.
- Summer heat makes the trail and market less comfortable midday.
Our Take
Downtown Winter Garden is one of the best food-and-stroll day trips from Lake Nona. The farmers market, Plant Street's restaurants and the trail make an easy Saturday, and the Garden Theatre and Friday music give you a reason to come back in the evening. Go early on market days, and check the events calendar before you pick a date.
What the Neighbors Know
Lake Nona residents often make downtown Winter Garden an occasional Saturday outing: the market in the morning, lunch on Plant Street and home by afternoon. It pairs well with visitors who want to see a historic Florida main street. For everyday dining closer to home, see our Lake Nona restaurants guide.
Official Sources
- Downtown Winter Garden events
- City of Winter Garden
- Garden Theatre
- Visit Orlando: Winter Garden
- Central Florida Expressway Authority (SR 417 tolls)
Buying or selling in Lake Nona? Call/Text David Myers at 407.801.3286 or use the contact form.
Frequently Asked Questions
How far is downtown Winter Garden from Lake Nona?
About 28 driving miles from Lake Nona Town Center. The usual route uses SR 417 and Florida's Turnpike, both toll roads, and avoids I-4.
When is the Winter Garden Farmers Market?
The Winter Garden Farmers Market is held on Saturday mornings at the downtown pavilion, a block off Plant Street.
What is Plant Street Market?
Plant Street Market is an indoor food hall in downtown Winter Garden with food and drink vendors, anchored by the Crooked Can Brewing Company.
Does the West Orange Trail go through downtown Winter Garden?
Yes. The paved West Orange Trail runs through downtown Winter Garden along Plant Street and continues for about 20 miles in total.
