Top 15 Attractions and Activities in Longwood, FL

Located north of Greater Orlando, Longwood is primarily a residential city with a steadily increasing population. The historic district encapsulates the essence of Longwood effectively.

Unlike a bustling downtown, Longwood features a tranquil grid of streets lined with elegant 19th-century homes and beautiful live oaks adorned with strands of Spanish moss.

In line with the wooded atmosphere, Big Tree Park is a hydric hammock that boasts some of the tallest and oldest bald cypress trees in the world.

This park can be accessed via the Cross Seminole Trail, one of two extensive multi-use trails running through Longwood.

Despite its serene vibe, there are a plethora of activities available in this city, including a weekly farmers’ market, regular concerts, scenic parks, and a highly regarded art fair held in November.

1. Cross Seminole Trail

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Longwood features two trailheads for this 23-mile trail that connects Winter Park to Lake Mary.

You can initiate your journey at Soldiers Creek Park or Big Tree Park, both situated within a lovely green corridor where Soldiers Creek flows into Lake Jesup.

Over the course of more than 20 years since the first section was inaugurated in 2002, the Cross Seminole Trail has progressively expanded. Ultimately, this route will be incorporated into the Florida Coast-to-Coast Trail, linking the Gulf and Atlantic coasts.

At present, it serves as an excellent means to explore the northern suburbs of Orlando, which are far more natural than one might anticipate. In Lake Mary, the trail connects with the Seminole Wekiva Trail, while in Winter Park, access to the Cady Way Trail is available.

2. Spring Hammock Preserve

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Located on the northeastern edge of Longwood, there exists a vast mosaic of habitats extending to the western shore of Lake Jesup.

The Cross Seminole Trail traverses the 1,100-acre Spring Hammock Preserve, providing an exceptional opportunity to witness what Central Florida appeared like prior to extensive development.

Along various waterways, including Soldier Creek, the preserve is characterized by hydric hammock, floodplain forest, pine flatwoods, and upland mixed hardwoods.

Boardwalk trails weave through the property, leading to the shores of Lake Jesup. During my visit, I noted that some of these boardwalks were in need of repairs.

Spring Hammock Preserve also encompasses Big Tree Park, which will be discussed later in this article.

3. Longwood Historic District

One of my preferred activities in any town is to explore on foot and uncover what I can find. The prime location for such exploration in Longwood is the historic district, situated a few square blocks east of Milwee St and west of CR 427.

On these tranquil streets, beneath stately live oaks and palms, are approximately 40 contributing buildings. One notable structure is the Bradlee-McIntyre House (c. 1885), maintained as a museum by the Longwood Historical Society.

Additionally, one should seek out the Longwood Hotel (1885), the Inside-Outside House (1873), and the Historic Civic Center (c. 1880), the latter of which is the oldest original building situated in Longwood.

The Inside-Outside House originally resided in Altamonte Springs and serves as an early model of a prefabricated residence. The current occupant is the Cottage Gift Shop, part of a small cluster of specialty stores in the district.

4. Longwood Arts and Crafts Festival

Each November, Longwood’s historic downtown awakens for a vibrant two-day arts and crafts fair. Initially hosted in the 1970s, the festival attracts over 200 artisans and craft exhibitors.

What distinguishes this event is the selection process for vendors, ensuring that displayed goods are unique.

Consequently, for those seeking exclusive items, this festival presents an outstanding opportunity. Attendees will discover jewelry, sculpture, photography, ceramics, glass art, paintings, hats, home decor, and much more.

During my visit, the festival had been recently recognized as one of the top 50 Best Contemporary/Classic Craft Fairs by Sunshine Artists’ annual list.

5. Big Tree Park

The Cross Seminole Trail leads visitors directly into this remarkable environment on the western side of Spring Hammock Preserve.

This hydric hammock swamp is home to some of the world’s oldest and largest bald cypresses. Notably, one of these trees, named The Senator, was tragically destroyed in a fire in 2012.

At that time, it was approximately 3,500 years old and stood 125 feet tall. During my visit, the remnants were cordoned off with a fence and marked with a plaque.

On a lighter note, there are numerous other magnificent specimens nearby. In close proximity is Lady Liberty, a tree believed to be over 2,000 years old, reaching nearly 90 feet in height.

6. Bradlee-McIntyre House

Source: (Ebyabe) / Wikimedia

This Victorian residence, built circa 1885, is the last of its kind in Seminole and Orange counties.

Originally constructed for affluent New England vacationers, the Bradlee-McIntyre House was relocated from Altamonte Springs to its present site in 1973.

The house is representative of Victorian Cottage and Queen Anne architectural styles, adorned with the intricate ornamentation typical of the late 19th century.

Upon relocation, the building was nearly derelict, but was meticulously restored by the Longwood Historical Society.

With its unique octagonal tower and 13 different rooms for exploration, the house now serves as the museum of the historical society.

Interestingly, shortly before my visit, the society successfully located an original washstand from this residence in Athens, Georgia. This significant artifact was returned to the house in 2021, dating back to the building’s earliest days.

7. Reiter Park

Adjacent to the historic district, Reiter Park serves as the natural venue for community events in Longwood.

On select Saturdays each month, the amphitheater hosts the Concerts in the Park series, where attendees can simply bring a lawn chair or picnic blanket and enjoy the performances as evening falls.

Every Saturday from 9:00 AM to 1:00 PM, the City of Longwood Farmers’ Market takes place at the amphitheater in Reiter Park. This market coincides with seasonal events, such as a children’s egg hunt at Easter.

As for amenities, the park offers a walking track, tennis courts, a basketball court, exercise equipment, picnic areas, pavilions, a playground, and a splash pad.

8. Seminole-Wekiva Trail

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Another popular multi-use trail in Longwood is the Seminole-Wekiva Trail, which extends 14 miles down to Altamonte Springs.

If you have an interest in history, you may find it fascinating that the trail follows the route of the former Orange Belt Railway (1888-1893).

This railway was one of the longest narrow gauge railroads constructed in the United States, stretching over 150 miles from Sanford to St. Petersburg.

On that note, the project was spearheaded by Russian exile Peter Demens (1850-1919), who owned a sawmill in Longwood.

Continuing along the trail, a particularly scenic section lies northeast of Longwood, where the path hugs the eastern bank of the Wekiva River. An optional detour leads into Markham Woods, featuring numerous mountain biking trails.

9. Paint the Trail

Source: Paint the Trail / Facebook

Along the Seminole-Wekiva Trail, a series of decorative panels enhance the cycling experience. These panels showcase Pop Art-style portraits of notable personalities. What is the story behind this initiative?

Artist Jeff Sonksen, facing redundancy during the recent global financial crisis, sought to take action. With his backyard fence bordering the trail, he began creating his own art on it.

Three years later, he invited homeowners throughout the trail to volunteer their fences for his artwork, creating a series of portraits stretching for miles.

Many years later, this remains my favorite section of the trail, extending for hundreds of feet both north and south of Dixon Rd.

10. Orlando Glass Blowing Center

Having changed ownership in 2020, this glassblowing studio in Longwood has become accessible to the public.

The Orlando Glass Blowing Center is a cozy facility where participants can experience the art of crafting glass through a variety of workshops and classes.

Equipped with high-quality glass-making tools, the studio is staffed by professional instructors.

Classes cater to all skill levels, whether you prefer individualized instruction or group sessions. Additionally, curious visitors can stop by to observe demonstrations.

11. Hourglass Brewing

Founded in 2012, this independent craft brewery offers a wealth of options to enjoy. Hourglass Brewing is deeply rooted in Central Florida and collaborates with numerous local businesses, promoting regional bands.

The expansive taproom in Longwood features pinball machines and is adorned with eclectic pop culture art and memorabilia, ranging from TMNT to Star Trek. Patrons can also view the brewing process through a clear observation area.

During my visit, there were over 20 beers on tap, representing a wide array of flavor profiles, from light to rich and malty. A particular favorite of mine was Get Dunked On, a malty Dunkelweizen.

Rather than food trucks, this brewery shares its space with two eateries, Wako Taco and Papa Bees (specializing in chicken wings).

12. Aiguille Rock Climbing Center

This indoor rock climbing gym in Longwood provides bouldering, top roping, and auto-belay options.

For first-time visitors who possess climbing experience, the process is swift and straightforward. After completing a waiver and taking a brief tour, individuals can utilize the facilities with a day pass.

If further instruction is needed, classes are available daily, although the schedule may vary, so it is advisable to verify beforehand.

The gym caters to climbers of all levels, offering 10,000 square feet of climbing space, with six auto-belays and five top rope walls.

Additionally, there is a comprehensive bouldering area and a pro shop where climbing gear such as shoes and chalk bags can be purchased.

13. Candyland Park

Candyland Park is a community park spanning nearly 18 acres in the northeastern part of Longwood. Nestled in one of Longwood’s older residential neighborhoods, it is replete with amenities.

Notable features include tennis courts, a skate park, a pump track, four baseball/softball fields, practice fields, basketball courts, a futsal court, a playground, and pickleball courts, among others.

The playground is particularly impressive, enclosed, and equipped with benches and bleachers. Furthermore, a concession stand typically operates during baseball games.

14. Secret Lake Park

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It is evident that Longwood boasts an impressive array of parks. If time permits, Secret Lake Park is located just five minutes away in Casselberry.

This park offers another fantastic opportunity for a stroll. Personally, I never tire of the diverse wildlife present in such locations. During my visit, I observed a wood stork, an owl, various ibises, and several snakes and alligators.

The park is situated along the shores of three lakes, making it an excellent launching point for kayaking. Additionally, there are boardwalks, tennis courts, multiple picnic pavilions, and the Casselberry Recreation Center.

15. Planet Obstacle

Source: Planet Obstacle / Facebook

This indoor entertainment center provides an engaging experience for children to expend energy. Spanning 50,000 square feet, Planet Obstacle is touted as the World’s Largest Indoor Obstacle Park, a claim that appears credible.

The facility includes an extreme zip-line, an aerial ropes course, a colossal rock-climbing adventure, and a dedicated adult ninja course. Additional attractions include trampolines, bumper cars, a ball pit, and a secure area for toddlers up to two years old.

Furthermore, Planet Obstacle features a Sky Cafe, perfect for a break after all the active fun. The menu offers an array of classic American comfort food, including vegetarian options.