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Maitland is a suburban city in Orange County, Florida, United States, part of the Greater Orlando area. The population was 19,543 at the 2020 census. The area's history is exhibited at the Maitland Historical Museum; the city also hosts the Maitland Art Center, as well as notable examples of Mayan Revival architecture and Fantasy architecture, the Maitland Telephone Museum, and the William H. Waterhouse House Museum (all museums and the Maitland Art Center are now managed by Art & History Museums of Maitland). A SunRail station is located in Maitland on Highway 17-92. The city is named for Fort Maitland.

The Maitland Art Center (formerly known as The Research Studio) is a historic site in Maitland, Florida. It was founded and designed by architect and artist J. Andre Smith (1880-1959) in 1937 as an artist colony, dedicated to experimental art. Funded by philanthropist Mary Curtis Bok, the colony hosted artists such as Ralston Crawford, Milton Avery, and Consuelo Kanaga. It is located at 231 West Packwood Avenue. On November 17, 1982, it was added to the U.S. National Register of Historic Places. The Maitland Art Center is one of the five museums encompassed by the Art & History Museums - Maitland (A&H). The A&H's Maitland Art Center offers artist residency programs, a variety of art classes for adults and children, professional development for artists, and dynamic programming for art appreciation. The A&H is a non-profit organization funded by earned income and contributions by the City of Maitland, the State of Florida, United Arts of Central Florida, grants, and individual donations. The A&H's Maitland Art Center is one of the few examples of Mayan Revival architecture, also known as Fantasy Architecture in the southeast. The grounds are a common location for outdoor weddings. The art center offers three areas for weddings: the Main Garden, the Chapel, and the Mayan Courtyard. The Center (as The Research Studio (Maitland Art Center)) was designated a National Historic Landmark in August 2014. It was given this designation primarily for its distinctive architecture, a Mayan-influenced interpretation of Art Deco, sometimes referred to as Mayan Revival.

Maitland Telephone Museum is a museum in Maitland, Orange County, Florida. It is operated by the Maitland Historical Society. The museum covers the history and development of the Winter Park Telephone Company. It is located at 221 West Packwood Avenue.

Maitland Historical Museum is a local history museum in Maitland, Florida, Orange County, Florida. It is operated by the Maitland Historical Society.

The William H. Waterhouse House is a historic residence in Maitland, Florida, United States, that is listed on the National Register of Historic Places.

Moseley House Museum is a house museum located in Eatonville, Florida. The house is the second oldest structure in the town, constructed in 1888. The house was owned by Jim and Matilda Clark Moseley, Matilda was the niece of Eatonville's founder and first mayor. Author Zora Neale Hurston was a friend of Matilda and often visited the house. The house was restored and opened as a museum in 2000. It currently exhibits early Eatonville memorabilia.

Maitland station is a train station in Maitland, Florida, served by SunRail, the commuter rail service of Central Florida. The station opened May 1, 2014, and marks the return of passenger rail service in Maitland since the days of the Atlantic Coast Line Railroad. It is the northernmost SunRail station in Orange County, Florida. Maitland is typical of most SunRail stations featuring canopies consisting of white aluminum poles supporting sloped green roofs and includes ticket vending machines, ticket validators, emergency call boxes, drinking fountains, and separate platforms designed for passengers in wheelchairs. The station is located along the former CSX A-Line (originally constructed by the South Florida Railroad) along the west side of US 17/92 just south of the SR 414 interchange. A transit-oriented development called The Parker at Maitland Station is located adjacent to the station and features a five-story, 293-unit luxury apartment community.Because the station currently averages the lowest ridership on the entire SunRail system with only 200 passengers a day, the City of Maitland constructed a pedestrian boardwalk that connects the station to the Greenwood Gardens neighborhood, which is located directly behind the station, in an effort to help boost ridership. Additionally, the city plans for the construction of a parking garage to be built at the station. Despite the current low ridership numbers in and out of the station, city officials believe there will be a need for the garage in the future. Plans call for the garage to be built sometime during the 2019 fiscal year. The city is not looking to pay for the construction of the garage, but rather, fund it using federal or state grant money.

The Zora Neale Hurston National Museum of Fine Arts, also known as The Hurston, is an art museum in Eatonville, Florida. The Hurston is named after Zora Neale Hurston, an African-American writer, folklorist, and anthropologist who moved to Eatonville at a young age and whose father became mayor of Eatonville in 1897. The museum's exhibits are centered on individuals of African descent, from the diaspora and the United States. The Hurston features exhibitions quarterly to highlight emerging artists.The museum supports the art involved within the museum and the Zora Neale Hurston Trail, which contains 16 historic artists and 10 markers written by Hurston. The museum is also featured in the Zora Festival, which is held every year to celebrate the history, culture, and arts of Eatonville. In January 2022, the Southern Poverty Law Center gave a $50,000 grant to the museum.

Eatonville is a town in Orange County, Florida, United States, six miles north of Orlando. It is part of the Orlando–Kissimmee metropolitan statistical area. Incorporated on August 15, 1887, it was one of the first self-governing all-black municipalities in the United States. The Eatonville Historic District and Moseley House Museum are in Eatonville. Author Zora Neale Hurston grew up in Eatonville and the area features in many of her stories. In 1990 the town founded the Zora Neale Hurston Museum of Fine Arts. Every winter the town stages the Zora Neale Hurston Festival of the Arts and Humanities. A library named for her opened in January 2004. The population was 2,159 at the 2010 census. The majority are African American.Artist Jules Andre Smith has done a series of paintings depicting life in Eatonville during the 1930s and 1940s. Twelve of these works are at the Maitland Art Center in the adjacent town of Maitland. Eatonville is home to WESH and WKCF, two television stations serving the Orlando television market.

Fort Maitland was a military fort built by the United States Army at what is now Maitland, Florida. It was built in November 1838 as a supply depot during the Second Seminole War. The fort was named after Captain W. S. Maitland, who was injured during the Battle of Wahoo Swamp and later killed himself after 9 months of trying to recover from his injuries.

Tijuana Flats Tex-Mex is a privately-held American restaurant chain serving Tex-Mex cuisine. It has over 135 locations (117 company owned and 18 franchised) throughout Florida, Georgia, North Carolina, Virginia, and Indiana. Tijuana Flats restaurants are fast-casual hybrids with fresh food, hot sauce bars, art murals and off-beat culture. Customers order at the front counter and are served after taking a seat. The restaurant was founded in Winter Park, Florida, in 1995 by University of Central Florida graduate Brian Wheeler with US$20,000 in loans. The company had 18 locations before expanding out-of-state in 2004.

Robert Hungerford Preparatory High School was a segregated high school for African Americans in Eatonville, Florida. The school was founded by Professor and Mrs. Russell C. Calhoun in 1897. Eatonville was one of the first African American towns to incorporate in the United States. It closed in 2010. Both the professor and his wife attended the Tuskegee Institute, of which the husband was a graduate. In the spring of 1898, along with the help of friends and relatives, Mr. E C. Hungerford donated to the school 160 acres (65 ha) of land. Mr. Hungerford of Chester, CT. owned a winter home in nearby Maitland, Florida. The land was donated in memory of his late doctor son, Robert, who died due to yellow fever. Robert had cared for a sick African American boy who no one else would help, even when Robert himself became ill. The groundwork for the school was possible thanks to donors not only from Florida, but throughout the country. The first cash donation for Hungerford was given by Miss Mary Brown of Winter Park, and the second was $400 was through Booker T. Washington of Tuskegee. Later on Mr. George B. Cluett, the head manufacturer of Troy, New York, donated $8,000 towards the construction of a second building, and an additional $4,000 towards the purchase of an orange grove near campus. Although Cluett Hall was burned in 1922, it was replaced by a stone structure bearing the same name only a year and a half later. Cluett also contributed a major sum towards the dining hall, which he himself insisted be named Calhoun Hall. Additionally, he gave $500 annually towards expenses for a number of years. By 1927, the school had expanded significantly. Originally only able to support a handful of students, the school now had over 100 boarding pupils, a number of day students, and also carried night classes for adults. A private school, Hungerford required each citizen to make personal arrangements in order to attend the institution. By 1938, Orange County began making arrangements for African American High School students of Winter Park to attend Hungerford, and commuted daily to the school by bus. Hungerford was a private school, offering grades 6 through 12 with dorms for both girls and boys. The institution was equipped with a "dining hall, chapel, library, manual training shops, laundry, home economics laboratory, barn, farm land and facilities for teaching business subjects."(Hall) It embraced both college preparatory and vocational, including subjects such as English, Latin, history, general science, biology, algebra, geometry, manual training (industrial arts), and home economics. The school also taught typing, bookkeeping, agriculture and physical education. As the 20th century progressed, classes in technical subjects such as mechanical drawing and radio were added. As for extracurricular activities, Hungerford took part in interschool sports, such as football, basketball and track. To instill responsibility, students were assigned "jobs and chores" outside of the classroom. These tasks involved helping maintain the school's dairy, chicken coops, gardens, classrooms and dormitories. To give back to the communities of Eatonville and Winter Park for their involvement, it had weekly Sunday afternoon Choral Concerts that were open to the public. In 1950, the Hungerford School became a public school administered by the Orange County School Board. The old, original campus buildings were replaced by new buildings. Today, the school still occupies a large parcel of land in Eatonville, just on the east side of the Interstate 4. The school closed its doors in 2010.