In 1916, Oldsmobile founder Ransom Eli Olds bought up this land at the north end of Tampa Bay to build a planned city.
Despite a huge marketing push, this was a financial disaster for Olds. His oil well never yielded any oil, and the proposed city of 100,000 had only attracted 200 people when he left town in the 1920s.
Every spring Oldsmar pays tribute to its curious heritage with the Oldsmar Days & Nights. Over three days there’s live music, a parade, a carnival, and a car show with Oldsmobiles.
I’m smitten with Oldsmar’s spectacular bayfront setting. At the likes of R.E. Olds Park you’ll be spellbound by the views over the bay and the light at sunset.
1. R. E. Olds Park
Along the city’s bayfront, R. E. Olds Park is dedicated to Oldsmar’s founder. I can’t get enough of this charming waterfront space, with its waterside trails and long pier jutting out 400 feet into the bay.
This structure is ADA accessible, and may be the best place to enjoy the sunset in Oldsmar. The remaining park gets pleasant breezes off the bay, and you can find a playground for kids, picnic shelters, and an area for dogs.
Throughout the year, different community events are held at the amphitheater here, including Oldsmar Days and Nights, which I’ll come to later in this article.
2. Empower Adventures
If you’re in need of some exhilaration, call in at Empower Adventures in Oldsmar. People from all over the Tampa area visit this spot for the longest and most exciting zip lines in the area.
I took the two-hour zip-line tour, and my feet literally did not touch solid ground the whole time. Along with 3,000+ feet of zip lines, there’s a 200-foot suspension bridge across the water, an aerial obstacle course, and rappelling to finish off.
At this height there are wonderful panoramas of the Oldsmar, Tampa Bay, and the Mobbly Bayou Wilderness Preserve.
3. Oldsmar Days & Nights
The top annual event in Oldsmar is also the oldest. Bringing three days of festivities every March, Oldsmar Days & Nights goes back more than 60 years.
As I mentioned, the base is R.E. Olds Park, and the unofficial motto is ‘Classic Cars, Classic Rock, Classic Florida’, which just about sums it up.
There’s live rock music throughout, as well as great food, a carnival, arts & crafts fair on the Friday, and a parade on the Saturday.
The latter exceeds 100 entries each year, and is followed by a car show featuring classic Oldsmobiles.
4. Oldsmar Historical Society
Wanting to know a bit more about Oldsmar’s past, I paid a visit to the Oldsmar Historical Society. This is in the historic Oldsmar Bank Building, dating to 1918.
Clad with white Italian glazed brick and Italian tiles, it’s the only original commercial building in situ in Oldsmar.
This was one of the first buildings erected by Ransom E. Olds, and has pride of place, right by City Hall.
Free to visit, the museum has exhibits about Mr. Olds, detailing his automobile empire, and why he chose to develop Oldsmar.
You can pore over archive photographs and artifacts, telling the story of Oldsmar from its founding through the present day.
5. Mobbly Bayou Wilderness Preserve
The Mobbly Bayou Wilderness Preserve is where you’ll find the adrenaline-inducing thrills of Empower Adventures.
But if you aren’t looking for a vertical thrill, the preserve has plenty of ground-based scenery to explore on foot.
This 400-acre preserve protects the kind of tidal creek system that has suffered due to development in this part of Florida.
Linking with Bicentennial Park you’ll find a paved walking trail, leading to a canoe/kayak launch, fishing dock, and lookout towers. For me, this is the best place to begin a paddling adventure on Tampa Bay.
And if you don’t have your own vessel, Empower Adventures offers private paddleboarding tour.
6. Mobbly Beach Park
On the west side of the Mobbly Bay peninsula I came across this little slice of paradise, looking west across the water to Safety Harbor.
Served by the Oldsmar Trail, Mobbly Beach Park is a small but exquisite piece of bayfront. This far south the peninsula has no development to speak of, apart from the road, Shore Drive. Behind that is the Mobbly Bayou Wilderness Preserve.
As for Mobbly Beach Park, there’s a lovely stand of live oaks, with a trio of picnic shelters and a series of workout stations under the canopy.
On the water, the beach is little more than a sliver of white sand. All the same, this is a heavenly place to hang out when the sun is setting.
7. Upper Tampa Bay Park
A couple of minutes out of Oldsmar, you can find the scenic grounds of Upper Tampa Bay Park.
On the Double Branch Peninsula, this 600-acre conservation park is both beautiful and historic. Along those lines, this area was occupied by the Tocobaga Native Americans up to the 16th century.
The undulations in the landscape are caused by middens composed of discarded shells and other refuse.
Named trails beckon you into a variety of habitats, from magnificent hardwood hammocks to mangroves, salt marsh and slash pine. Wildlife abounds here, and I appreciated the interpretive booths pointing out the main species.
Also make time for the nature center, which has live exhibits, with snakes, fish, and turtles.
8. HorsePower For Kids & Animal Sanctuary
Run by a nonprofit organization, this attraction is a place for kids to interact with farm animals. Most of the experiences here are aimed at children aged nine and under.
These include pony rides, hayrides, and seeing, meeting or interacting with a wide assortment of barnyard and exotic species.
These might be pigs, sloths, goats, capybaras, peacocks, camels, horses, cockatiels, parrots, tortoises, and alpacas. You can purchase cups of feed for many of these residents.
Another feature I found really neat is the playground, sitting in a picture-perfect grove, complete with tire swings and zip lines.
9. Veterans Memorial Park
Along the waterfront near R.E. Olds Park, this park is smaller, but no less scenic than its neighbor.
If you’re looking to escape it all, Veterans Memorial Park is a go-to. Set in a secluded area overlooking Tampa Bay, the park has benches by the water where you can watch the sun go down.
There’s a gazebo at the highest point, and, given the backdrop, I don’t think it’s a mystery why this is a cherished setting for wedding photos.
The park was opened in 2006, in honor of all veterans of the armed services, and has a stirring memorial by the parking lot.
10. Oldsmar Flea Market
For a bargain hunter like me, the Oldsmar Flea Market is one of the best places to visit in the city. Originating in 1980 with self-storage sales in 1980, this immense market is one of the largest on Florida’s Gulf Coast.
Head here for anything from fresh produce to furniture, fashion accessories, books, used video games, tools, sporting goods, plants, musical instruments, pet supplies, jewelry, and a lot more.
After a brief period of decline, a new era arrived in 2018 when it was purchased by a St. Petersburg entrepreneur. Even though there are still a few empty booths, the market was full of treasures when I came.
11. Tampa Bay Downs
Late November through early May there’s international-standard horse racing a couple of minutes away at Tampa Bay Downs. This track first opened in 1926 and continues to host a long list of graded stakes races.
A couple of important events are the Tampa Bay Derby in March, and the Hillsborough Stakes, in the same month.
As with all race tracks in Florida, Tampa Bay Downs has added new gaming facilities since the 2000s. So, you’ve got a 25-table poker room, and simulcast horse racing to keep things buzzing all year.
I’m also a big fan of the golf practice facility that opened here about 20 years ago. There’s a 40-station driving range, a full-size putting green, two chipping greens, PGA instructors, and a proshop.
12. Oldsmar Trail
I think I’ve shown that Oldsmar has a wonderful roster of public parks, especially on Tampa Bay. One way to reach them is on this 10-mile paved trail system, working its way through the city.
The nexus point is R.E. Olds Park, and from there the Oldsmar Trail branches out in three directions. You can head south to Mobbly Bayou Beach Park, north to Cypress Forest Park, or northwest along the Lake Tarpon Canal to the Oldsmar Sports Complex.
A total of ten parks are connected by the trail. So, if you have a pair of wheels you could spend some time getting acquainted with Oldsmar in a new way. The views, from the bay to the canal, to stands of bald cypress, live oak, pines, and palms, are often sublime.
13. Tampa Bay Skating Academy
Ice skating might not seem like the first activity that comes to mind on Florida’s gulf coast. Yet, given the notoriously hot and sunny days for much of the year, you might just welcome the cold interior of a skating rink.
With two sheets of ice Tampa Bay Skating Academy is part of a network of public rinks in the Tampa Bay area. You can take part in public skate sessions every day of the week at this facility.
There’s also casual skate & shoot, pick-up hockey games and freestyle slots, as well as a host of programs, mainly aimed at teaching kids to skate, or coaching hockey skills.
A variety of youth and adult hockey teams use this facility, and you can come to watch games throughout the season.
14. Bicentennial Park
This little park is linked by a trail to Empower Adventures and the Mobbly Bayou Wilderness Preserve.
Bicentennial Park is a range of active amenities, for basketball, tennis, pickleball, and shuffleboard. There’s a variety of exercise equipment along the trail, if you want to get a workout.
Oldsmar’s main dog park is also at this spot, while you can fish in the large reservoir on the south side. Most impressive was the playground, which looked brand new when I came by, and has a wood chip surface.
15. AMC Woodlands Square 20
There’s a high-end AMC multiplex at the Woodlands Square shopping center in Oldsmar. More than just another theater, this is a true entertainment destination.
That’s got a lot to do with the IMAX screen, which is easily the best way to see a major release. Another of the auditoriums here is a Dolby Cinema, with an ultra-vivid screen, and immersive Dolby Atmos sound.
Every screen at AMC Woodlands Square 20 has reclining, Lazyboy-style seats. Honestly, I’d urge you to pick something exciting to watch, because I’ve been known to fall asleep in these seats.