15 Best Things to Do in Maitland (FL)

Located in central Florida’s Orange County, Maitland is a northern suburb of Orlando that had a population of about 17,000 residents at the time of the last census.

Most visitors and residents agree that despite its proximity to one of the state’s largest urban areas, Maitland has a decidedly quaint and suburban feel that makes it the perfect destination for those savvy travelers who want the best of both worlds.

Close to world-class beaches, theme parks, and a number of natural and historical attractions, it’s the perfect place to hang your hat while exploring the Sunshine State.

Below are 15 things to do in and around Maitland, Florida.

1. Maitland Historical Museum

The Maitland Historical Museum is operated by the Maitland Historical Society. Its exhibits and displays cover a huge span of time that begins well before the area was officially discovered and settled by non-Native Americans.

The area was once the exclusive realm of the Seminole tribe. In their language, the land on which the town now resides was named after natural melons that provided much of the people’s sustenance.

The museum is divided into two distinct sections, one which covers the history, settlement, and development of the town, and one which delves into the interesting history of the local telephone company.

2. Maitland Art Center

For a relatively small rural town, Maitland has its fair share of fascinating historical and cultural attractions; the Maitland Art Center is one of its most significant.

The center has a history that stretches back to the late ‘30s and features architecture that’s unique to the area and referred to as Mayan Revival Style.

The center is located on West Packwood Avenue. For much of its existence, it was an artist’s colony that gave established and aspiring artists a place to live while honing their skills.

The center is now listed on the National Register of Historic Places and is a convenient, unique, and inexpensive local attraction.

3. Luke’s Kitchen and Bar

Orlando is a big tourist town, and many locals lament that many of its restaurants are little more than tourist traps offering gobs of unimaginative, pre-prepared meals aimed at customers they know they’ll only see once.

Located on South Orlando Avenue in Maitland, Luke’s Kitchen and Bar is the perfect antidote for those who’d rather eat fresh food prepared by professional chefs in a memorable setting.

Previous customers have noted that Luke’s atmosphere was a pleasant mix of trendy, contemporary, relaxed, and casual that they found appealing.

Combined with their full menu of classic American fare, it’s definitely a place to check out when in need of nourishment.

4. Howell Branch Nature Preserve

Located on Temple Drive in Winter Park, Howell Branch Nature Preserve is comprised of just slightly more than 10 acres, making it small by Florida nature preserve standards. But its grounds include a wide variety of natural habitats, like wetlands and forests, that offer guests many recreation options.

From playgrounds and fitness trails to its towering observation deck, the preserve is a must-visit site for outdoorsy and nature-loving types who’ve tired of Orlando’s more commercial attractions.

Deer, foxes, snakes, and a variety of birds call the park home and are commonly seen along the trails, especially in the lowlight morning and afternoon hours.

5. Maitland Rotary Art Festival

Since 1976, the small town of Maitland has been hosting a popular annual art festival, and it takes place over three days in November.

The Maitland Rotary Art Festival is held in scenic Lake Lily Park. Though it started small, it’s blossomed into one of the region’s most popular art events and has done an amazing job at bringing artists and art lovers together, as well as shining a spotlight on the community in general.

In addition to browsing the art and watching artists work, there’s plenty of live entertainment, great food and drink, and a variety of activities that are fun for the whole family.

6. Maitland Farmer’s Market

There’s probably no other state in the country that has more farmer’s markets per capita than Florida, and with its abundant sun, rain, and temperate weather, it’s no wonder.

The Maitland Farmer’s Market takes place every Sunday from 9 AM to 2 PM at Lake Lily Park on Maitland Avenue. In addition to offering amazing seasonal produce, arts and crafts, and health and body products, it also hosts live entertainment. It is an all-around fun community event that shouldn’t be passed up.

There’s plenty of free parking on-site, and many visitors choose to arrive early to enjoy a coffee and some baked goods before doing their shopping.

7. The Winter Garden Heritage Museum

Located just a few minutes from Maitland, Winter Garden is another central Florida town that offers visitors lots of options, especially for those who are interested in history, culture, and development.

The Winter Garden Heritage Museum was founded in 1998 and is chock-full of interesting artifacts and memorabilia that relate to the city’s architecture, founding, and economy.

The museum is housed in an old depot that dates back to 1918, and it’s staffed by knowledgeable and enthusiastic volunteers who keep it open every day from 1 until 5 PM.

Much of what visitors see centers on the area’s founders and settlers and the ever-important citrus industry.

8. Lake Apopka

For freshwater fisherman from all over the country, Florida holds quite an allure because it’s known to have some of the best bass fishing found anywhere.

Located in nearby Winter Garden, Lake Apopka has always been a hotspot for anglers looking to tangle with some of the state’s largemouth bass that are known to reach epic proportions.

Fishing is still a popular attraction, but the lake is also a big draw for pleasure boaters, bird watchers, hikers, and lovers of magnificent sunsets.

During peak times, the lake’s developed park areas can get downright crowded, so don’t expect to have the place to yourself.

9. Horseback Riding

Florida has always been big horse country, and most out-of-staters don’t know that the Sunshine State has a cowboy tradition that rivals more traditional Old West states like Texas and Arizona.

The countryside around Winter Garden and Maitland is full of horse farms and equestrian centers that offer a variety of services and activity options; many of them are appropriate for those who’ve never even looked at a real live horse.

In addition to lessons and guided trail rides, the centers host many special events. Many of them are free and offer visitors a unique insight into a slice of local culture that doesn’t get much fanfare.

10. West Orange Trail

During the summer months, the weather in Florida can be nothing short of brutal, but for much of the year, it’s absolutely perfect, making outdoor recreation a popular pastime.

Central Florida’s West Orange Trail is a multi-use trail that’s open to walkers, runners, bikers, and horseback riders. It stretches for more than 20 miles and includes multiple access points between Oakland and Apopka.

The trail winds its way through a fantastic diversity of natural and manmade environments that include wetlands, forests, farmlands, and neighborhoods. In many of the more developed areas, there are a variety of historic, retail, and dining attractions close by.

11. Central Florida Railroad Museum of Winter Garden

The railroads have played significant roles in Florida’s development, and for train and railroad aficionados with some extra time on their hands, there’s no place more worthy of a visit than the Central Florida Railroad Museum of Winter Garden.

The museum is located in Winter Garden’s historic downtown area and is housed inside an old railroad depot from a bygone era. Staff-led tours are available.

In past years, the area’s two main railroads were the Tavares and Gulf Rail and Atlantic Coast Lines. The museum’s exhibits include equipment, artifacts, photographs, and first-hand accounts of those who worked in the industry.

12. Tupperware Confidence Museum

When most people think of Florida’s world-famous tourist attractions, The Tupperware Confidence Museum isn’t generally near the top of the list. But for lovers of fresh food and those who prefer the quirky and offbeat to the touristy and done-to-death, a trip to the aforementioned museum would be a great way to spend a few morning or afternoon hours.

The museum is dedicated to the fantastic history of the Tupperware company; all joking aside, it’s full of amazing things that most guests find both entertaining and enlightening.

It’s free to visit and open from Monday to Friday from 10 in the morning until 4 in the afternoon.

13. Jack Kerouac House

Jack Kerouac is one of the titans of the literary movement referred to as the ‘Beat Generation’ that exploded onto the pop-culture scene in the middle part of the 20th century.

Most known for his books, On the Road and The Dharma Bums, like many authors of the day, Kerouac was into a variety of the counter culture’s most popular pastimes, like drugs, alcohol, Buddhism, and free-love.

Though many of those things didn’t sit well with more traditional Americans, the movement produced some great works, and the museum is a truly unique destination for literature enthusiasts and aspiring writers.

14. Museum of Osteology

From meat and cartilage devouring beetles to fully-intact dinosaur skeletons, the Museum of Osteology is one of Orlando’s most unique attractions. It draws an amazingly diverse crowd of visitors – from med students and scientists to school children and lovers of the macabre.

The museum has been open for just a few years, but its impressive collection includes more than 500 real skeletons. In addition to its public role, the company that operates the facility provides skeletons to universities and research institutions around the world.

There are a variety of interactive exhibits, and the museum is one of those rare places that entertains and educates simultaneously.

15. Holy Land Experience

Though crucifixion and resurrection aren’t common travel experiences, for those who’d rather not check their faith at the door just because they’re on vacation, the Holy Land Experience in Orlando would be a solemn and poignant place to spend an hour or two.

The facility is owned by a Christian television station and is dedicated to bringing the history of the Holy Land to modern-day Florida. Their main attractions include lifelike and historically accurate villages and daily reenactments of some of the Bible’s more memorable moments.

Be warned that some of the reenactments are a bit too realistic for some visitors.