15 Best Things to Do in Maitland (FL)

Around 15 minutes north of downtown Orlando, Maitland is an affluent suburban city in a beautiful environment. Water dominates the townscape here, with more than 20 individual lakes.

Many of Maitland’s public parks sit next to these water bodies, and I adore the stands of moss-draped live oaks and tall bald cypresses.

In the 1930s the city became home to an experimental art colony, which survives today as part of the Art & History Museums of Maitland. The complex’s astonishing Mayan Revival architecture has earned it National Historic Landmark status.

Elsewhere in Maitland are also important institutions covering topics as varied as the Holocaust and birds of prey. There’s also a dynamic social calendar, with events like the Florida Film Festival and the juried Maitland Rotary Art Festival.

Finally, with the SunRail commuter train you can get to nearby communities like Winter Park in minutes.

1. Maitland Art Center

The Art & History Museums of Maitland took shape in 2010 with a merger between the city’s historical society and the Maitland Art Center.

The center has a history stretching back to a colony for experimental art founded in 1937. For me, the extraordinary architecture by the founder André Smith (1880-1959) is a big draw.

These are some of the only surviving buildings in the Mayan Revival style, a form of Art Deco. In 2014, the complex became the very first site in Central Florida to be declared a National Historic Landmark.

Couched in stunning gardens, the buildings are adorned with more than 2,000 carvings and murals.

There are two galleries for contemporary exhibitions, along with a feast of public art programming, and two residency programs for professional artists.

To fully appreciate the Art Center complex, look out for an upcoming National Historic Landmark Tour.

2. Maitland Historical Museum

In fact, several of the attractions in my list are part of the Art & History Museums of Maitland. This goes for the enlightening Maitland Historical Museum, with exhibits covering a huge timespan, beginning with Timucua Native Americans.

In these galleries you can pull on several different threads, from Maitland’s foundation in 1885 to the once burgeoning citrus industry.

I was completely absorbed in the exhibits about Maitland’s early ties to the Florida Audubon Society, which held its first meeting here in 1900.

3. Audubon Center for Birds of Prey

Maitland was the site of the very first meeting of the Florida Audubon Society. This was in 1900, at a time when Florida’s wading birds were suddenly under threat from human encroachment.

Today there’s a center in the city, continuing that tradition of conservation. The Audubon Center for Birds of Prey is dedicated to rescuing, treating, rehabilitating and releasing Florida’s raptors.

Visiting the center, I was able to get closer than ever to owls, falcons, kites, ospreys, and bald eagles. Every bird has its own moving story, and the staff are happy to tell it.

You can also check out exhibits on bird conservation, rehabilitation, and the effects of climate change in Central Florida.

4. Holocaust Memorial Resource Center and Education Center of Florida

In Maitland you’ll find one of America’s oldest institutions devoted to the remembrance and study of the Holocaust.

The Holocaust Memorial Resource & Education Center goes back to a project begun by Tess Wise, a local Survivor from Poland. When I wrote this article there were plans to build a state-of-the-art new center in downtown Orlando.

For now though there are sobering, expertly researched exhibits next to the Jewish Academy of Orlando.

The permanent exhibit, Holocaust in History, charts the origins, progress and aftermath of this period in history, with artifacts, documents, photographs and personal accounts.

On my visit there was an exhibition about the players and officials of the soccer team FC Bayern Munich who were persecuted under National Socialism.

5. Enzian Theater

Maitland is home to the only full-time independent cinema in Central Florida. Opened in 1985, the Enzian Theater started out as a repertory theater showing classic movies.

Things have evolved over the last 40+ years, and now you can watch first-run independent movies, as well as plenty of older movies, from Golden Age Hollywood to cult classics. Food is at the heart of the experience, courtesy of the Eden Bar, and table service adds a touch of luxury.

As a regional hub for independent cinema, this theater stages a lot of festivals throughout the year. The standout is the Florida Film Festival in April, an Oscar-qualifying festival dating back more than three decades.

6. Lake Lily Park

If I had to choose the prettiest park in Maitland, this place would surely be a contender. On the shore of the almost perfectly circular Lake Lily, the park is linked to the heart of the city by a paved trail, running south from Independence Square.

Lake Lily Park is the venue for the long-running Maitland Rotary Art Festival, which I’ll cover in more detail below. Also here is the Waterhouse Residence Museum, appearing later in my list too.

Above all the park is a place where you can unwind. Shaded by a dense canopy there’s a half-mile trail, with an elevated boardwalk along the eastern shore.

Sheltered by the trees is a children’s playground, while there’s an idyllic gazebo for weddings on the water.

7. Waterhouse Residence Museum

At this home by Lake Lily you’ll find out about the middle-class family life in Maitland during the Gilded Age. The Waterhouse Residence was built in 1884 for one William H. Waterhouse and his family, and is replete with period details.

Everything, from the kitchen to the bedrooms, is presented as it might have looked in the late 19th century.

The standout feature is the staircase, fashioned from hand-turned heart-of-pine in the Eastlake style. Touring the museum you’ll see a trove of local Victoriana, including quilts, clothing, and furniture, while learning about the Waterhouse family.

8. Maitland Telephone Museum

Also at the Art & History Museums of Maitland complex is a museum dedicated to telephone technology in and around Maitland.

With the help of artifacts and hands-on displays, you can see how telecommunications have evolved over time.

For instance, there’s a telex machine, a working switching station, and a timeline of telephone devices. These include wooden wall-mounted phones and a lot of rotary dials.

Most fascinating for me was the story of the Winter Park Telephone Co. This came about in 1910, when the son of a local grocery store owner installed phones at the residences of regular customers to help them place orders.

9. Maitland Community Park

Crowded with trees including live oaks and bald cypresses, this park has a name that doesn’t do credit to its beauty, in my opinion.

My favorite way to enter Maitland Community Park is from the east side where there’s 600 feet of picturesque boardwalk. This takes you through the densely wooded banks along the creek that links Lake of the Woods with Lake Minnehaha.

In the glades further west are numerous amenities. To name a few, you’ve got pavilions, racquetball courts, tennis courts, and a concession stand in the community building.

10. Minnehaha Park

In Maitland’s stellar array of public parks there’s another fantastic lakefront space on the southern shore of Lake Minnehaha.

This waterbody is part of a long chain, with Lake of the Woods in the north and Lake Maitland in the south. From the lakeshore and along the canal you can watch boats, kayaks and paddleboards coming and going.

I adore the little boardwalk trail by the water here, with interesting signs informing you about the wetland plants and wildlife. Also at Minnehaha Park are playgrounds for various ages, as well as an exercise trail for adults.

11. Orlando Ice Den

The top hockey rink in Central Florida is on the west side of Maitland. My pick for rainy or excessively hot days, the Orlando Ice Den has two sheets of ice, NHL regulation and the other Olympic size.

A great thing about a facility on this scale is that there are plenty of public skating slots. In fact, when I was around there was a public skating session every day of the week. Admission is $15 on weekdays and $18 on weekends, with skate rental included.

The Orlando Ice Den also has a host of programs for figure skating and hockey, from leagues for all ages to skate & shoot sessions.

12. Winter Park

Maitland is contiguous with another well-heeled community, also in a townscape laced with water. In fact you could head over to Winter Park to rent a canoe, kayak or paddleboard, and then paddle your way back into Maitland.

For something less strenuous, you could join the scenic boat tour, with tours on the Winter Park Chain of Lakes, departing on the hour between 10:00 am and 4:00 pm daily.

Just one stop on the SunRail, Winter Park has a lot to love. There’s an upscale downtown along Park Avenue, stately architecture, another flourishing farmers’ market, and a boat load of culture to dive into.

My go-to is the Charles Hosmer Morse Museum of American Art, with its astounding inventory of pieces by Louis Comfort Tiffany (1848-1933).

13. Maitland Rotary Art Festival

Since 1976, the small town of Maitland has hosted a juried art festival over three days in November.

Held in scenic Lake Lily Park, the Maitland Rotary Art Festival started small, but has blossomed into one of the region’s most popular art events.

This event brings artists and art lovers together, but I also appreciate how it raises money for important local causes.

There are more than 130 carefully selected artists from across the Southeast. These have a wide range of specialties, from glassmaking to painting, ceramics and photography.

There’s also plenty of live entertainment, great food and drink, and a variety of fun family activities.

14. Maitland Farmers’ Market

The city has a vibrant farmers’ market, taking place every Sunday from 9:00 am to 1:00 pm along Independence Lane downtown.

Some of the items that caught my eye were raw honey, straight from the honeycomb, and delicious fresh kettle corn.

In addition to amazing seasonal produce, arts and crafts, and health and body products, there’s weekly live entertainment. This is an all-around fun community event that I can’t recommend enough.

If you’re from colder climes like me, you’ll be amazed by the Christmas themed events in December, at a time when farmers’ markets are normally in the middle of a long winter break.

15. Maitland Jazz and Blues Festival

Independence Square is the location for Maitland’s biggest annual music event. This two-day shindig in late March/early April welcomes major international performers from the worlds of jazz and blues.

There are two stages on opposite sides of the park, one for each genre, with a long bill of performers stretching into the late evening.

This event had just taken place when I was in town. Some performers from the most recent edition were Pat Travers, Lucy Yeghiazaryan, Michelle Amato, Charlie Bertini, and Bobby Blackmon.

For food and drink, there’s a cluster of spots around Independence Square, including a branch of the Sanford Brewing Company.