Top 15 Attractions and Activities in Maitland, FL

Situated approximately 15 minutes north of downtown Orlando, Maitland is an affluent suburban city characterized by its picturesque environment. The town’s landscape is prominently defined by an abundance of water, featuring more than 20 individual lakes.

Numerous public parks in Maitland are located adjacent to these lakes, surrounded by majestic stands of moss-draped live oaks and towering bald cypresses. 

In the 1930s, the city became home to a pioneering art colony, which continues to thrive today as part of the Art & History Museums of Maitland. The complex is distinguished by its remarkable Mayan Revival architecture, earning it National Historic Landmark recognition. 

Maitland also hosts significant institutions exploring diverse themes, including the Holocaust and birds of prey. The city boasts a vibrant social calendar featuring events such as the Florida Film Festival and the juried Maitland Rotary Art Festival.

Additionally, the SunRail commuter train provides swift access to neighboring communities such as Winter Park.

1. Maitland Art Center

Source: ebyabe / Flickr

The Art & History Museums of Maitland were established in 2010 through a merger between the city’s historical society and the Maitland Art Center. 

The center’s origins trace back to a colony for experimental art founded in 1937. The remarkable architecture crafted by founder André Smith (1880-1959) serves as a primary attraction. 

These buildings represent some of the few surviving examples of Mayan Revival architecture, a variation of Art Deco. In 2014, the complex achieved recognition as the first site in Central Florida designated as a National Historic Landmark. 

Set amidst stunning gardens, the buildings feature over 2,000 distinct carvings and murals. 

The center accommodates two galleries dedicated to contemporary exhibitions, along with extensive public art programming and two residency programs for professional artists. 

To gain a comprehensive understanding of the Art Center complex, look for an upcoming National Historic Landmark Tour.

2. Maitland Historical Museum

Source: Ebyabe / Wikimedia

Numerous attractions on this list are part of the Art & History Museums of Maitland. Among these is the enlightening Maitland Historical Museum, featuring exhibits that span a significant timeframe, starting with the Timucua Native Americans. 

The galleries present multiple narratives, from Maitland’s establishment in 1885 to the once-thriving citrus industry. 

I found the exhibits detailing Maitland’s historical connections to the Florida Audubon Society, which convened its first meeting here in 1900, to be particularly engaging.

3. Audubon Center for Birds of Prey

Maitland hosted the inaugural meeting of the Florida Audubon Society in 1900, at a time when the region’s wading birds faced significant threats due to human encroachment.

Today, the city hosts a dedicated center that continues the mission of conservation. The Audubon Center for Birds of Prey focuses on the rescue, treatment, rehabilitation, and release of Florida’s raptors.

During my visit to the center, I had the opportunity to observe owls, falcons, kites, ospreys, and bald eagles up close. Each bird has its own compelling story, which the staff is enthusiastic to share. 

Additionally, the center features exhibits on bird conservation, rehabilitation, and the impacts of climate change in Central Florida.

4. Holocaust Memorial Resource Center and Education Center of Florida

Maitland is home to one of the oldest institutions in the United States dedicated to the remembrance and study of the Holocaust.

The Holocaust Memorial Resource & Education Center originated from a project initiated by Tess Wise, a local survivor from Poland. While I was researching this article, plans were underway for the construction of a modern new center in downtown Orlando.

Currently, there are meticulously curated, poignant exhibits adjacent to the Jewish Academy of Orlando. 

The permanent exhibition, “Holocaust in History,” chronicles the origins, progression, and aftermath of this historical period, featuring artifacts, documents, photographs, and personal testimonies.

During my visit, there was an exhibition focusing on the players and officials of the soccer club FC Bayern Munich who faced persecution under National Socialism.

5. Enzian Theater

Maitland is distinguished by housing the only full-time independent cinema in Central Florida. Established in 1985, the Enzian Theater began as a repertory theater showcasing classic films.

Over the years, the venue has evolved to feature first-run independent films alongside numerous older classics, from the Golden Age of Hollywood to cult favorites. A notable aspect of the experience is the dining offered by Eden Bar, complemented by table service for added luxury.

As a regional hub for independent film, this theater hosts several festivals throughout the year, with the Florida Film Festival in April being a particular highlight. This Oscar-qualifying festival has been a staple for over three decades.

6. Lake Lily Park

If tasked with determining the most aesthetically pleasing park in Maitland, this location would undoubtedly be a strong contender. Situated along the shore of the almost perfectly circular Lake Lily, the park connects to the heart of the city via a paved trail leading south from Independence Square.

Lake Lily Park serves as the venue for the long-standing Maitland Rotary Art Festival, an event I will detail further below. Also located here is the Waterhouse Residence Museum, which will be covered later in this article.

Above all, the park is an ideal retreat, offering a shaded half-mile trail, complete with an elevated boardwalk along the eastern shore. 

Nestled under the trees is a children’s playground, along with a picturesque gazebo suitable for weddings by the water.

7. Waterhouse Residence Museum

At this residence by Lake Lily, visitors can explore insights into middle-class family life in Maitland during the Gilded Age. The Waterhouse Residence was constructed in 1884 for William H. Waterhouse and his family, retaining numerous period details.

The interiors, spanning from the kitchen to the bedrooms, are presented as they might have appeared in the late 19th century. 

A standout feature is the staircase, crafted from hand-turned heart-of-pine in the Eastlake style. As you tour the museum, you will encounter a rich collection of local Victoriana, including quilts, clothing, and furniture, while learning about the Waterhouse family.

8. Maitland Telephone Museum

Also located within the Art & History Museums of Maitland complex is a dedicated museum exploring the evolution of telephone technology in and around Maitland. 

Through artifacts and interactive displays, visitors can gain insights into the advancements in telecommunications over time. 

Exhibits include a telex machine, a functioning switching station, and a timeline showcasing various telephone devices, from wooden wall-mounted phones to numerous rotary dials.

Particularly captivating was the history of the Winter Park Telephone Company, established in 1910 when the son of a local grocer initiated phone installations at residential client homes to facilitate order placements.

9. Maitland Community Park

Enveloped by trees, including live oaks and bald cypresses, this park’s name fails to capture its remarkable beauty, in my opinion. 

My preferred entry point into Maitland Community Park is from the east side, where a picturesque 600-foot boardwalk traverses the densely vegetated banks along the creek, which connects Lake of the Woods to Lake Minnehaha. 

Further west, the park boasts numerous amenities, including pavilions, racquetball courts, tennis courts, and a concession stand within the community building.

10. Minnehaha Park

Among Maitland’s impressive collection of public parks, Minnehaha Park features another exceptional lakefront area, situated along the southern shore of Lake Minnehaha.

This waterbody is part of an extensive chain, extending from Lake of the Woods in the north to Lake Maitland in the south. Visitors can observe boats, kayaks, and paddleboards navigating the waters along the lakeshore and adjacent canal.

I particularly appreciate the small boardwalk trail that borders the water, equipped with informative signs detailing the wetland plants and wildlife. Minnehaha Park also includes playgrounds designed for various age groups, as well as an exercise trail for adults.

11. Orlando Ice Den

The premier hockey rink in Central Florida is located on the west side of Maitland. I recommend the Orlando Ice Den as a top choice on rainy or excessively hot days, featuring two sheets of ice—one NHL regulation and the other Olympic size. 

A significant advantage of this facility is the abundance of public skating sessions available. In fact, during my visit, there were public skating sessions daily. Admission is $15 on weekdays and $18 on weekends, which includes skate rental. 

The Orlando Ice Den offers numerous programs for figure skating and hockey, accommodating participants of all ages in leagues, as well as skate and shoot sessions.

12. Winter Park

Maitland is adjacent to another affluent community characterized by a landscape interspersed with water features. Visitors can easily venture over to Winter Park to rent canoes, kayaks, or paddleboards and paddle back into Maitland.

For those seeking a more relaxed experience, a scenic boat tour on the Winter Park Chain of Lakes is available, with departures on the hour between 10:00 am and 4:00 pm daily.

Just one stop on the SunRail, Winter Park offers a wealth of attractions. Visitors can explore an upscale downtown along Park Avenue, admire stately architecture, enjoy another thriving farmers’ market, and immerse themselves in a rich cultural experience. 

Personally, I recommend the Charles Hosmer Morse Museum of American Art, which houses an outstanding collection of works by Louis Comfort Tiffany (1848-1933).

13. Maitland Rotary Art Festival

Source: The Maitland Rotary Art Festival / Facebook

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

Taking place in the scenic Lake Lily Park, the Maitland Rotary Art Festival has evolved from humble beginnings into one of the region’s most anticipated art events.  

This festival unites artists and art enthusiasts, and I particularly value its role in supporting crucial local initiatives. 

Featuring over 130 carefully selected artists from across the Southeast, the festival highlights various specialties, including glassmaking, painting, ceramics, and photography. 

The event also offers a variety of live entertainment, exceptional food and drink options, and engaging family activities.

14. Maitland Farmers’ Market

Source: Maitland Farmers Market / Facebook

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

Among the items I discovered were raw honey, fresh from the honeycomb, and delicious kettle corn. 

In addition to remarkable seasonal produce, the market features arts and crafts, health and body products, and live entertainment each week. This community event offers a delightful experience that I highly recommend. 

If you hail from colder regions, the Christmas-themed events in December will surely impress, especially since farmers’ markets usually take an extended winter break during this time.

15. Maitland Jazz and Blues Festival

Independence Square serves as the venue for Maitland’s largest annual music event. This two-day festival, held in late March or early April, draws major international artists from the jazz and blues genres.

Two stages, positioned on opposite sides of the park, host a continuous lineup of performances stretching well into the evening. 

This event had recently concluded during my visit. Notable performers from the latest edition included Pat Travers, Lucy Yeghiazaryan, Michelle Amato, Charlie Bertini, and Bobby Blackmon. 

For food and beverages, visitors can explore various options surrounding Independence Square, including a branch of the Sanford Brewing Company.