Family Day Out Ideas in Winter Park, FL (2026): 12 Local Picks

Looking for the family day out ideas near you in Winter Park? Here are 12 family outings worth the trip, starting with Winter on the Avenue and Winter Park Christmas Parade, with what each one does best and how to get there.

12 picks · Updated October 2026

1
Winter on the Avenue

Event in Park Avenue
A free early December evening on Park Avenue with tree and menorah lighting, snow slides, s'mores and an outdoor movie. Santa arrives by fire truck for photos.
- Family
- Kids
- Christmas
- Free
Website for Winter on the Avenue (opens in a new tab)Directions to Winter on the Avenue (opens maps)
2
Winter Park Christmas Parade

Event in Park Avenue
A morning parade down Park Avenue on the first Saturday of December, billed as Central Florida's oldest continuous holiday parade, with marching bands, first responders and Santa at the end.
- Family
- Kids
- Christmas
- Parade
Website for Winter Park Christmas Parade (opens in a new tab)Directions to Winter Park Christmas Parade (opens maps)
3
Winter Park 4th of July Celebration

Event in Park Avenue
A free small-town Independence Day evening in Central Park with a children's bike parade, a kids' zone and free pie, cake and ice cream while they last.
- Family
- Kids
- Summer
- Festival
Website for Winter Park 4th of July Celebration (opens in a new tab)Directions to Winter Park 4th of July Celebration (opens maps)
4
Winter Park Autumn Art Festival

Event in Park Avenue
A free November art show of Florida artists in Central Park and along Park Avenue, with a children's art workshop area and live music.
- Family
- Kids
- Art festival
- Festival
Website for Winter Park Autumn Art Festival (opens in a new tab)Directions to Winter Park Autumn Art Festival (opens maps)
5
Mead Botanical Garden

Park
Free natural garden in Winter Park with shaded trails, a boardwalk, a creek and a pond that draws wading birds and turtles. An amphitheater on site hosts performances and community events.
- Family
- Free
- Outdoor
- Nature
Call Mead Botanical Garden Website for Mead Botanical Garden (opens in a new tab)Directions to Mead Botanical Garden (opens maps)
6
Scenic Boat Tour

Tour in Park Avenue, $
Hour-long narrated boat ride through Winter Park's chain of lakes and connecting canals, leaving hourly from the foot of Morse Boulevard. Tickets are $20 for adults and $10 for kids, first come first served.
- Family
- Outdoor
- Water
- Date idea
Call Scenic Boat Tour Website for Scenic Boat Tour (opens in a new tab)Directions to Scenic Boat Tour (opens maps)
7
Winter Park Farmers' Market

Market in Park Avenue
City-run Saturday morning market in Central Park's West Meadow off Park Avenue. Vendors sell produce, plants, baked goods, coffee and specialty foods.
- Family
- Outdoor
- Free
- Local favorite
Call Winter Park Farmers' Market Website for Winter Park Farmers' Market (opens in a new tab)Directions to Winter Park Farmers' Market (opens maps)
8
Winter Park Sidewalk Art Festival

Event in Park Avenue
Running since 1960, this volunteer-led juried art show fills Central Park and Park Avenue each March, drawing more than 250,000 visitors.
- Family
- Art festival
- Festival
- Spring
Call Winter Park Sidewalk Art Festival Website for Winter Park Sidewalk Art Festival (opens in a new tab)Directions to Winter Park Sidewalk Art Festival (opens maps)
9
Christmas in the Park (Winter Park)

Event in Park Avenue
The Morse Museum opens Winter Park's holiday season by displaying lit Tiffany stained-glass windows in Central Park for one evening. The Bach Festival Choir and Brass Ensemble perform a holiday concert alongside them.
- Family
- Christmas
- Outdoor
- Local favorite
Website for Christmas in the Park (Winter Park) (opens in a new tab)Directions to Christmas in the Park (Winter Park) (opens maps)
10
Winter Park History Museum

Museum in Park Avenue
Free museum just off Park Avenue covering Winter Park's past, from its citrus era onward, through rotating exhibits. A monthly family day adds kid-friendly tours and story time.
- Family
- Free
- Indoor
- Rainy day
Call Winter Park History Museum Website for Winter Park History Museum (opens in a new tab)Directions to Winter Park History Museum (opens maps)
11
Howell Branch Preserve

Park
Small Winter Park nature preserve of about 10 acres ringed by wetlands, with a boardwalk and lookout deck for taking in the habitat. A fitness trail, playground and picnic pavilion make it an easy short outing.
- Family
- Walking
- Boardwalk
- Nature
Call Howell Branch Preserve Website for Howell Branch Preserve (opens in a new tab)Directions to Howell Branch Preserve (opens maps)
12
Ward Park

Park
Large 66-acre Winter Park park packed with ballfields, tennis courts and an Olympic-size pool, plus an asphalt walking path and a trail that passes through wetlands.
- Family
- Walking
- Running
- Paved trail
Call Ward Park Website for Ward Park (opens in a new tab)Directions to Ward Park (opens maps)

Year-round family outings

For a dependable day out in any season, start with the Orlando Science Center, Gatorland or the Audubon Center for Birds of Prey. The Science Center is indoors and works for all ages, with KidsTown for younger children. Gatorland is open daily 10am to 5pm, rain or shine, and has gator shows, a petting area and add-ons like a zip line for older kids. The Audubon Center takes about an hour and is closed Mondays. Fort Christmas Historical Park is free and pairs history with a playground. For toddlers, Abracadabra Play & Café in Winter Garden is indoors, air-conditioned and accepts walk-ins.

About this list

Every place here is a locally run business in Orange County with its own website, which we checked for hours, menus and contact details. We leave national chains off our best-of lists and favor places with a clear specialty.

This page covers 12 family outings in Winter Park. You'll find them in Park Avenue.

What comes up again and again on their menus and websites: Bach Festival Choir and Brass Ensemble concert.

About Winter Park

Winter Park sits just north of Orlando and is known for Park Avenue, Rollins College, its chain of lakes and brick streets. The city has a dense cluster of independent restaurants, boutiques, salons and professional offices.

Frequently asked questions

What can families do in Winter Park besides theme parks?

The Orlando Science Center, Gatorland, the Audubon Center for Birds of Prey and Nona Adventure Park are popular non-theme-park outings. Free county parks such as Barber Park and Dr. P. Phillips Community Park have splash pads, and Fort Christmas Historical Park offers free history programs.

Where are free splash pads in Winter Park?

Barber Park, Capehart Park, Barnett Park and Dr. P. Phillips Community Park all have free splash pads run by Orange County. Barber and Capehart run timed sessions from 10am to 6:45pm with a break from 2 to 3pm, and hours at Dr. P. Phillips change with the season.

What is a good rainy day activity for kids in Winter Park?

The Orlando Science Center is the top rainy-day pick, with four floors of hands-on exhibits and a dome theater. For toddlers, Abracadabra Play & Café in Winter Garden is an indoor play cafe for ages 0 to 7. Gatorland stays open rain or shine if your family does not mind getting a little wet.

Are there free family events in Winter Park?

Yes. Winter on the Avenue, the Winter Park 4th of July Celebration and the Winter Park Autumn Art Festival are free. Fort Christmas Historical Park offers free history programs, and Orange County parks with splash pads are free to visit.

Is there u-pick fruit near Winter Park?

Tom West Blueberries in Ocoee is one of the few u-pick farms inside Orange County. It is closed for 2026 and expects to reopen in March 2027. Season dates depend on the crop, so call ahead before you go.