Towards the north of Greater Orlando, Longwood is a mostly residential city with a growing population. For me, the historic district sums up Longwood neatly.
Rather than a bustling downtown, this is a peaceful grid of streets with ornate 19th-century residences and beautiful live oaks with streams of Spanish moss.
On the wooded theme, Big Tree Park is a hydric hammock with some of the tallest and oldest bald cypresses in the world.
You can get there along the Cross Seminole Trail, one of two long multi-use trails passing through Longwood.
Despite its understated atmosphere, there’s a lot to do in this city. There’s a weekly farmers’ market, regular concerts, picturesque parks, and a high-ranking art fair in November.
1. Cross Seminole Trail
Longwood has two trailheads for this 23-trail that works its way from Winter Park to Lake Mary.
You can begin your journey at Soldiers Creek Park or Big Tree Park, both within the beautiful green corridor where Soldiers Creek flows into Lake Jesup.
The Cross Seminole Trail has gradually joined up over 20+ years since the first segment opened in 2002. Eventually this route will become part of the Florida Coast-to-Coast Trail, connecting the Gulf and Atlantic coasts.
For now I think it’s a fine way to explore Orlando’s northern suburbs, which are much more natural than you might expect. In Lake Mary the trail links with the Seminole Wekiva Trail, while in Winter Park you can get onto the Cady Way Trail.
2. Spring Hammock Preserve
On Longwood’s northeastern edge there’s a large mosaic of habitats extending to the western shore of Lake Jesup.
The Cross Seminole Trail passes through the 1,100-acre Spring Hammock Preserve. For me, it’s a wonderful way to see what Central Florida looked like before it was developed.
Along several watercourses, including Soldier Creek, the preserve is made up of hydric hammock, floodplain forest, pine flatwoods, and upland mixed hardwoods.
Boardwalks streak through the property, and continue to the shore of Lake Jesup. When I was here, some of these walkways were in need of renovation.
Spring Hammock Preserve also comprises Big Tree Park, which I’ll come to later in this list.
3. Longwood Historic District
One of my favorite things to do in any town is take to the streets on foot and see what I can find. The best place to do that in Longwood is the historic district, a few square blocks east of Milwee St and west of CR 427.
On sleepy streets, under stately live oaks and palms are some 40 contributing buildings. One of these is the Bradlee-McIntyre House (c. 1885), maintained as a museum by the Longwood Historical Society.
Also look out for the Longwood Hotel (1885), the Inside-Outside House (1873), and the Historic Civic Center (c. 1880). The latter is the oldest original building in situ in Longwood.
The Inside-Outside House was originally in Altamonte Springs, and is an early example of a prefab residence. The current occupant is the Cottage Gift Shop, one of a clutch of little specialty stores in the district.
4. Longwood Arts and Crafts Festival
Every November Longwood’s historic downtown springs to life for this two-day arts and crafts fair. First held in the 1970s, the festival welcomes more than 200 and hand craft exhibitors.
Something special about this event is that vendors are selected according to their uniqueness.
So, If you want to get hold of something truly one-off, I don’t think you can do much better. You’ll find jewelry, sculpture, photography, ceramics, art glass, painting, hats, a trove of home decor, and tons more.
When I was in town the festival had just ranked as a top 50 Best Contemporary/Classic Craft Fair in Sunshine Artists’ annual list.
5. Big Tree Park
The Cross Seminole Trail leads you right into this unforgettable environment on the west side of Spring Hammock Preserve.
The hydric hammock swamp here features some of the oldest and largest bald cypresses on the planet. One was The Senator, which was sadly destroyed in a fire in 2012.
At that time it was 3,500 years old and stood 125 tall. When I came through, the remnants were marked with a fence and a plaque.
On the lighter side, there are a lot of other awesome specimens around. Close by is Lady Liberty. This tree is believed to be well over 2,000 years old and reaches close to 90 feet in height.
6. Bradlee-Mcintyre House
The only surviving building of its kind in Seminole and Orange counties, this Victorian house was built around 1885.
Built for wealthy New England vacationers, the Bradlee-Mcintyre House was originally located in Altamonte Springs, but was moved to its current spot in 1973.
It is an example of Victorian Cottage and Queen Anne style architecture, and abounds with the rich ornamentation associated with the late 19th century.
At that time the building was almost derelict, but was carefully restored by the Longwood Historical Society.
With an unusual octagonal tower, and 13 different rooms to explore, the house serves as the historical society’s museum.
Not long before I visited something really interesting had happened, as the society had managed to locate an original washstand from this residence in Athens, Georgia. This item was returned to the house in 2021, and is remarkable as it dates back to the building’s earliest days.
7. Reiter Park
Abutting the historic district, Reiter Park is the natural setting for community events in Longwood.
Once a month on select Saturdays, the amphitheater here hosts the Concerts in the Park series. All you have to do is bring a lawn chair or picnic blanket and enjoy the show as the sun goes down.
Every Saturday, 9:00 am to 1:00 pm, the City of Longwood Farmers’ Market takes place at the amphitheater in Reiter Park. I love how this coincides with seasonal events, like 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
Another multi-use trail serving Longwood is the Seminole-Wekiva Trail, which continues for 14 miles down to Altamonte Springs.
If you’re a frustrated historian like me, you might be interested to know that the trail is on a piece of the old Orange Belt Railway (1888-1893).
This was one of the longest narrow gauge railroads ever built in the United States, running for more than 150 miles from Sanford to St. Petersburg.
On that topic, the driving force behind the project was Russian exile Peter Demens (1850-1919). He owned a sawmill right here in Longwood.
Back on the trail, there’s a very scenic part northeast of Longwood where the path touches the east bank of the Wekiva River. For a detour you can also pedal off into Markham Woods, which has miles of mountain biking trails.
9. Paint the Trail
On the Seminole-Wekiva Trail, there is a panel of fences that brightens up your ride. A string of Pop Art-style portraits of famous personalities adorn the panels. So what’s it all about?
Artist Jeff Sonksen was made redundant during the recent global financial crisis and decided to do something about it. His backyard fence bordered the trail, so he started painting his own artwork on it.
Three years later, he has asked homeowners all along the trail to volunteer their fences to his artwork in the hope of creating a series of portraits that stretches for miles.
Several years later, this is still my favorite part of the trail, running for hundreds of feet north and south of Dixon Rd.
10. Orlando Glass Blowing Center
Since changing hands in 2020, this glassblowing studio in Longwood has been opened up to the public.
The Orlando Glass Blowing Center is an intimate space where you can learn the joy of crafting art glass through a variety of workshops and classes.
The studio is filled with high-quality glass-making equipment, and is staffed by professional instructors.
There are classes for all standards, whether you want one-on-one instruction, or would prefer to join a group. If you’re just curious you can always just drop by to watch a demonstration.
11. Hourglass Brewing
This independent craft brewery was founded in 2012 and has a lot to love about it. Rooted in Central Florida, Hourglass Brewing partners with a host of local businesses, and helps put local bands in the spotlight.
The taproom in Longwood is massive, with pinball machines, and walls plastered with quirky pop culture art and memorabilia, from TMNT to Star Trek. There’s also a clear view on the brewhouse and its fermentation tanks.
There were more than 20 beers on tap when I paid a visit. These cover the whole spectrum of flavor profiles, from light to rich and malty. As a fan of darker beers, I loved Get Dunked On, a malty Dunkelweizen.
Instead of food trucks, this brewery shares a building with two eateries, Wako Taco and Papa Bees (chicken wings).
12. Aiguille Rock Climbing Center
This indoor rock climbing gym in Longwood offers bouldering, top roping and auto-belay climbing.
For first-time visitors who are experienced climbers, the process is quick and easy. After filling out a waiver and taking a brief tour, you’ll be free to use the facilities with a day pass.
If you’re in need of more instruction, there are classes every day of the week, although the exact times differ, so you’ll need to check the website.
The gym has something for everyone, from beginners to experienced climbers. There’s 10,000 square feet of climbing, with six auto-belays and five top rope walls.
Added to that is an extensive bouldering area, and a proshop where you can pick up climbing shoes, chalk bags, and other gear.
13. Candyland Park
Longwood’s community park covers almost 18 acres in the northeastern corner of the city. Couched in one of Longwood’s older residential areas, Candyland Park is absolutely packed with amenities.
I’ll do my best to list them here. So, you’ve got tennis courts, a skate park, pump track, four baseball/softball fields, practice fields, basketball courts, a futsal court, a playground, and pickleball courts, to name just a few.
The playground is impressive, and is fenced, with benches and bleachers. Finally, there’s also a concession stand, which is normally open during baseball games.
14. Secret Lake Park
I think I’ve shown that there’s an astonishing abundance of great parks around Longwood. If you have time for another, Secret Lake Park is barely five minutes away in Casselberry.
This is yet another stellar spot for a walk. For my part, I’ll never get tired of the sheer amount of wildlife visible at places like this. In the space of an hour I saw a wood stork, an owl, ibises, and a number of snakes and alligators.
The park is on the shores of three lakes, and is a prime place to launch a kayak. There’s also a boardwalk, tennis courts, several picnic pavilions, and the Casselberry Recreation Center.
15. Planet Obstacle
This indoor fun center is a great day out for the kids, allowing them to blow off a lot of steam. Planet Obstacle is massive, with 50,000 square feet of attractions. In fact, it calls itself the World’s Largest Indoor Obstacle Park, and I don’t think it’s hyperbole.
There’s an extreme zip-line, aerial ropes course, a giant rock-climbing adventure, and an adult ninja course. You’ve also got bungees, trampolines, bumper cars, a ball pit, and a safe zone for wee ones up to two.
Planet Obstacle includes a Sky Cafe, for a pit stop after all the high-energy fun. There’s a lot of classic American comfort food, with veggie options included.