18 Best Things to Do in Maitland, FL

Maitland, FL
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Located in Orange County in Central Florida, Maitland is a quaint suburban city and part of the greater Orlando area.

Despite its proximity to Disneyland, Maitland also has a unique personality and feel that makes it an exciting destination.

Close to several natural and historical tourist spots, world-class beaches, and theme parks, Maitland is the perfect place to represent Florida.

Here are the 18 best things to do in Maitland, FL:

Visit the Maitland Historical Museum

Front view of Maitland Historical Museum's exterior
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The Maitland Historical Society operates the Maitland Historical Museum, which offers a quick history lesson about the area.

The exhibits and displays cover a broad period that begins way before the discovery of Maitland,

For example, the exhibits feature the Native Americans who lived in the area before the US Army established 'Fort Maitland' in 1838.

Side facade of Maitland Historical Museum
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Maitland was once the land of the Native American Seminoles.

Its initial name was "Fumecheliga," or "Muskmelon Place," since the area was abundant in melons, which fed the first settlers.

The Maitland Historical Museum features two distinct sections: one covers the history and development of the city.

At the same time, the other one delves deep into the unique and exciting history of the local telephone company, the Winter Park Telephone Company.

Appreciate Local Art at the Maitland Art Center

Exterior of Maitland Art Center
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

History and art are two themes that Maitland, FL, is most known for.

Maitland has a fair share of historical and cultural attractions for a relatively small city.

The Maitland Art Center is one of them.

Plants on Maitland Art Center's courtyard
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Located on West Packwood Avenue, the Maitland Art Center is a cultural haven for local artists who want a safe place to live while displaying their skills with the brush and paint.

This art center also showcases the rich history of Maitland's architecture, referred to as the "Mayan Revival Style."

Listed on the National Register of Historic Places, the Maitland art center is a convenient and inexpensive place to visit while you explore the beauty and uniqueness of Maitland's art scene.

Wall designs of Maitland Art Center
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Try Fine Dining at Luke's Kitchen and Bar

Maitland and all of its surrounding areas have a lot of tourist attractions to visit and exciting places to see.

If all of this touring makes you tired and hungry, take a break and dine at Luke's Kitchen and Bar.

It's a contemporary-industrial restaurant located on South Orlando Avenue.

Luke's Kitchen and Bar is about experience and food, featuring patio seating with an open kitchen for an up-close look at the chef's culinary creations.

The restaurant's menu offers American comfort food classics with a modern twist to tantalize your taste buds.

Their selection of craft beers and wines is also a must-try.

Take a Scenic Walk around Lake Lily Park

A water fountain in the middle of Lake Lily Park's waters
Jesse Kunerth / Shutterstock.com

If you want to take a peaceful and serene walk in Maitland, then stroll around Lake Lily Park.

Lake Lily is a ten-acre artificial lake in the heart of Maitland that is perfect for a peaceful afternoon walk.

Night lights illuminating Lake Lily Park's pathway
Scott MacLeod7 / Shutterstock.com

The park also features many playgrounds, pavilions, and a dog park, making it the perfect place for the whole family.

The park also hosts several local events throughout the year, so see what's happening during your stay in Maitland, FL.

Birds near the water of Lake Lily Park
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Celebrate Art at the Maitland Rotary Art Festival

The best time for art lovers to visit Maitland, FL, is November because of the annual Maitland Rotary Art Festival.

This three-day art festival is in the scenic Lake Lily Park and showcases the works of over 200 local and national artists.

This yearly celebration of art and culture started in 1976 as a small art-appreciation event that became one of the most famous art events in the region.

Through the years, the Maitland Rotary Art Festival has done a phenomenal job bringing artists and art enthusiasts together, shining a spotlight on the general community and its commitment to showcasing the arts.

You can also support local businesses as many set up booths during the festival.

Besides browsing the art and meeting artists, there's also live entertainment, food, drinks, and other great family-oriented activities.

Enjoy the Great Outdoors at the West Orange Trail

The paved pathway of West Orange Trail
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The perfect weather in Florida is why outdoor recreation is the locals' favorite pastime.

The West Orange Trail is a 22-mile paved trail located in the northwest part of the Orlando metropolitan area that's perfect for walking, running, biking, and rollerblading.

The trail is also popular among picnickers and bird watchers as it passes through many parks, including Lake Apopka Wildlife Drive.

There are also several historical, retail, and dining attractions nearby that you can also check out.

The West Orange Trail is free to use.

Visit a Horse Farm

Most people not from Florida would be surprised to know that the state is a big horse country.

The Sunshine State has a rich cowboy tradition that rivals even the well-known cowboy-culture states like Arizona and Texas.

The countryside around Maitland and Winter Garden teems with horse farms and equestrian centers, so it's no wonder why horseback riding is one of the most popular things to do in the area.

The area offers various activities, perfect for visitors who've never seen or ridden a horse before.

Guided trail rides and horseback riding lessons are also available for learning more about this fascinating activity.

Go Birdwatching at the Audubon Center for Birds of Prey

A crested caracara at Audubon Center for Birds of Prey
Andrea Westmoreland from DeLand, United States, CC BY-SA 2.0, via Wikimedia Commons

Maitland has a bird of prey rehabilitation center open to the public for tours and birdwatching.

The Audubon Center for Birds of Prey is on Lake Sybella in a restored two-story lakefront bungalow.

The center is home to several kinds of birds or prey—bald eagles, owls, ospreys, and kites—that have been injured or orphaned.

There's also a gift shop where you can buy souvenirs and other items to bring home.

Grab a Sub at Kappy's Subs

It's hard to visit Maitland, FL, without tasting the delicious subs at Kappy's Subs.

This local sandwich shop is famous for its fresh-baked bread, huge portions, and reasonably-priced menu.

Kappy's Subs is also known for its made-to-order cheesesteaks and grilled ham and cheese subs.

However, with its wide selection of sandwiches and snacks, you can't go wrong with anything on the menu.

Visit the Waterhouse Residence Museum

Front view of Waterhouse Residence Museum's exterior
Cloberto, CC BY-SA 4.0, via Wikimedia Commons

The Waterhouse Residence Museum is a historic house museum in Maitland.

The museum is on Lake Lily Drive, known for being one of the oldest remaining structures in Maitland.

Information board on the grounds of Waterhouse Residence Museum
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

This museum was the family home of pioneer settler William H. Waterhouse in 1884.

The Waterhouse Residence Museum has been restored to depict the time of the Waterhouse family and their middle-class lifestyle during the late Victorian era.

Buy Fresh Oranges at Hollieanna Groves

You can't leave Maitland without bringing home many of its world-famous oranges.

You can pick your oranges or purchase citrus fruits at Hollieanna Groves, a family-owned farmer's market in Maitland.

Holleanna Groves specializes in fresh citrus fruits, but they also sell honey, jams, jellies, and other locally made products.

The best time to visit Hollieanna Groves is during the citrus season, from December until March.

Shop at the Maitland Farmers Market

Thanks to the area's temperate weather, it's no wonder Florida is well-known for its abundance of farmer's markets.

The Maitland Farmers Market is a prime destination for buying fresh, locally-sourced produce, dairy, and other food items.

The Maitland Farmers Market is one of the best places to shop for fresh and healthy food.

You'll also find several food trucks and other vendors selling prepared foods, arts, and crafts.

This is also a great place to mingle with the locals and learn more about the community.

Other Things to Do Nearby

Visit the Winter Garden Heritage Museum

Exterior of Winter Garden Heritage Museum
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Winter Garden is another attractive little city located in central Florida worth visiting.

For example, you can visit the Winter Garden Heritage Museum.

Take a 27-minute drive from downtown Maitland to reach the Winter Garden Heritage Museum.

It offers many options for visitors, especially those interested in the area's culture, history, and development.

A train caboose in front of Winter Garden Heritage Museum
Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

Opening in 1998, the Winter Garden Heritage Museum is full of historical artifacts and exciting memorabilia depicting the city's founding, architecture, and growing economy.

The museum itself is a historic site housed in an old depot from 1918.

Knowledgeable volunteers give guided tours every day from 1:00 p.m. until 5:00 p.m.

Other must-see exhibits at the Winter Garden Heritage Museum feature the city's founder, the original settlers, and the area's prosperous citrus industry.

Bond with Nature at Howell Branch Nature Preserve

Located on Temple Drive in Winter Park—an eight-minute drive from downtown Maitland—Howell Branch Nature Preserve is a ten-acre natural preserve featuring a wide variety of Floridian wildlife.

While ten acres is relatively tiny by Florida standards, Howell Branch Nature Preserve offers various natural habitats such as forests and wetlands.

From fitness trails and playgrounds to its iconic observation deck, Howell Branch Nature Preserve offers many recreational options for guests.

The Howell Branch Nature Preserve is a must-visit to experience Florida outdoors.

Explore the trails while seeing alligators, deer, foxes, and a plethora of birds that make the preserve their home.

Hike along the Lake Apopka Wildlife Drive

The waters of Lake Apopka Wildlife Drive
Debi Ford / Shutterstock.com

One of the best things to do in Maitland, FL, is to explore the great outdoors.

There's no better place than the Lake Apopka Wildlife Drive.

Located in Apopka—a 27-minute drive from downtown Maitland—the Lake Apopka Wildlife Drive is a 4.5-mile one-way loop perfect for wildlife watching, birding, and photography.

An anhinga at Lake Apopka Wildlife Drive
Andrew Shue / Shutterstock.com

There's also a 1.5-mile walking trail near the southern end of the drive to stretch your legs and get some fresh air.

The best time to visit the Lake Apopka Wildlife Drive is during the cooler months, from October to March.

The place teems with alligators, bald eagles, sandhill cranes, and other exciting wildlife.

Visit the Tupperware Confidence Museum

The Tupperware Confidence Museum is a unique attraction and an exciting place to visit in Maitland, FL.

Located on Highway 441 Orange Blossom Trail—a 26-minute drive from downtown Maitland—the Tupperware Confidence Museum is dedicated to the iconic brand's history and founder, Earl Silas Tupper.

The museum is small but packed with interesting artifacts, including Tupperware products from different eras, photographs, and marketing materials.

The Tupperware Confidence Museum is free to enter.

Visit the Jack Kerouac House

Exterior of Jack Kerouac House
Ebyabe, CC BY-SA 4.0, via Wikimedia Commons

Located on Clouser Avenue, the Jack Kerouac House is a national historic site and a must-visit for literature and Beat Generation fans.

The house is where the famous writer lived when he wrote his novel On the Road, which has since become a museum open to the public.

A large tree shading Jack Kerouac House
Visitor7, CC BY-SA 3.0, via Wikimedia Commons

The museum is small but packed with fascinating memorabilia, including Kerouac's typewriter, personal belongings, and photographs.

Admission is free at the Jack Kerouac House.

Check Out the Central Florida Railroad Museum

Exterior of Central Florida Railroad Museum's depot
MikeFlorida, CC BY-SA 4.0, via Wikimedia Commons

Florida's development owes much to its railroad system.

The Central Florida Railroad Museum is a great place to learn more about this vital part of the state's history.

The museum is on South Boyd Street in Winter Garden, a 28-minute drive from downtown Maitland.

It's also inside a restored Tavares and Gulf depot built in 1913.

The museum features several exciting exhibits, including a working model railroad, a passenger car, and a caboose.

There's also a variety of equipment, photographs, artifacts, and first-hand accounts of people who have worked in Florida's railroad industry.

Final Thoughts

If you're looking for a fun-filled weekend getaway or a more extended vacation destination, Maitland should be high on your list.

With its convenient location, variety of things to do, and friendly atmosphere, Maitland is the perfect place to unwind and relax.

Have you been to Maitland, Florida?

If not, add it to your list of places to visit in Florida!

Discover More of Orange County, FL

Things to Do in Apopka, FL

Things to Do in Winter Garden, FL

Things to Do in Winter Park, FL

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