Top 15 Attractions and Activities in Oldsmar, Florida

In 1916, automotive pioneer Ransom Eli Olds acquired this property at the northern end of Tampa Bay with the intention of establishing a planned community.

Despite extensive promotional efforts, this endeavor turned out to be economically unviable for Olds. His oil drilling efforts were fruitless, and the envisioned city of 100,000 residents attracted a mere 200 occupants when he departed in the 1920s.

Every spring, Oldsmar honors its intriguing heritage with the Oldsmar Days & Nights festival. Over the course of three days, this event features live music, a parade, a carnival, and a car exhibition showcasing Oldsmobiles.

Oldsmar’s stunning bayfront environment captivates visitors. At R.E. Olds Park, one can be mesmerized by breathtaking views across the bay, particularly during sunset.

1. R. E. Olds Park

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Situated along the city’s bayfront, R. E. Olds Park is a tribute to Oldsmar’s founder. This delightful waterfront space offers scenic paths and a lengthy pier extending 400 feet into the bay.

This location is fully accessible and might be the premier spot for watching sunsets in Oldsmar. The park enjoys lovely breezes from the bay and features a playground, picnic pavilions, and designated areas for dogs.

Throughout the year, various community functions take place at the amphitheater, including the aforementioned Oldsmar Days and Nights festival.

2. Empower Adventures

Source: zipontampabay.com

For those seeking adventure, Empower Adventures in Oldsmar provides thrilling experiences. Individuals from across the Tampa area flock to this location for the region’s most extensive and exhilarating zip lines.

On my two-hour zip line tour, I barely touched solid ground the entire time. Along with over 3,000 feet of zip lines, participants traverse a 200-foot suspension bridge, navigate an aerial obstacle course, and conclude their adventure with rappelling.

At these heights, one can enjoy stunning vistas of Oldsmar, Tampa Bay, and the Mobbly Bayou Wilderness Preserve.

3. Oldsmar Days & Nights

The most notable annual event in Oldsmar is also its longest-running. Hosted for three days every March, Oldsmar Days & Nights has been celebrated for over 60 years.

The base for the event is R.E. Olds Park, and the unofficial motto is ‘Classic Cars, Classic Rock, Classic Florida,’ which encapsulates the festival’s essence.

This event features live rock music, delectable food, a carnival, an arts and crafts fair on Friday, and a parade on Saturday.

The parade consistently exceeds 100 entries each year and is followed by a car exhibition featuring classic Oldsmobiles.

4. Oldsmar Historical Society

Source: City of Oldsmar, FL – Government / Facebook

To gain insights into Oldsmar’s history, I visited the Oldsmar Historical Society, located in the historic Oldsmar Bank Building dating back to 1918.

This building, adorned with white Italian glazed brick and tiles, is the only original commercial structure still standing in Oldsmar.

It was one of the first buildings erected by Ransom E. Olds and holds a prominent position near City Hall.

Visitors can explore the museum free of charge, which features exhibits about Mr. Olds, highlighting his automotive legacy and his decision to develop Oldsmar.

Artifacts and archival photographs narrate Oldsmar’s story from its inception to the present day.

5. Mobbly Bayou Wilderness Preserve

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The Mobbly Bayou Wilderness Preserve is home to the exhilarating adventures provided by Empower Adventures.

If zip-lining isn’t your preference, the preserve offers ample ground-level scenery to explore on foot.

This 400-acre preserve safeguards a tidal creek ecosystem that has faced challenges due to urban development in this region of Florida.

The preserve connects with Bicentennial Park and features a paved walking trail that leads to a canoe/kayak launch, fishing dock, and elevated observation towers. This area is ideal for initiating a paddling excursion on Tampa Bay.

If you lack personal equipment, Empower Adventures provides private paddleboarding excursions.

6. Mobbly Beach Park

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On the western side of the Mobbly Bay peninsula, I discovered this serene oasis, looking westward across the water toward Safety Harbor.

Accessed via the Oldsmar Trail, Mobbly Beach Park is a modest yet stunning piece of bayfront. In this southern area of the peninsula, there is minimal development, aside from Shore Drive. Behind this road lies the Mobbly Bayou Wilderness Preserve.

Mobbly Beach Park features a charming stand of live oaks, complemented by three picnic shelters and fitness stations nestled under the canopy.

In terms of beachfront, it offers a slender strip of white sand. Nonetheless, this location provides a pristine atmosphere, particularly during sunset.

7. Upper Tampa Bay Park

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Just a few minutes outside of Oldsmar, one can explore the beautiful grounds of Upper Tampa Bay Park.

Located on the Double Branch Peninsula, this conservation park spans 600 acres and is also rich in history. This area was once inhabited by the Tocobaga Native Americans until the 16th century.

The varied topography results from middens formed by discarded shells and other refuse.

Well-marked trails lead visitors through diverse habitats, including magnificent hardwood hammocks, mangroves, salt marshes, and slash pine forests. Wildlife is abundant in this area, and interpretive kiosks highlight the primary species found here.

Allocate some time to visit the nature center, which features live exhibits including snakes, fish, and turtles.

8. HorsePower For Kids & Animal Sanctuary

This nonprofit venture provides an opportunity for children to interact with various farm animals. Most programs cater to children aged nine and under.

Activities include pony rides, hay rides, and the chance to observe and interact with a wide array of barnyard and exotic animals.

Among the residents are pigs, sloths, goats, capybaras, peacocks, camels, horses, cockatiels, parrots, tortoises, and alpacas. Visitors can purchase cups of feed to interact with many of these animals.

Another appealing feature is the picturesque playground, complete with tire swings and zip lines.

9. Veterans Memorial Park

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Situated along the waterfront near R.E. Olds Park, this park, although smaller, is equally scenic.

For those seeking tranquility, Veterans Memorial Park is an excellent retreat. Nestled in a secluded area that overlooks Tampa Bay, the park features benches where visitors can relax and admire sunset views.

A gazebo is positioned at the highest vantage point, and given its picturesque location, it has become a popular choice for wedding photography.

Established in 2006, the park honors all veterans of the armed services and features a poignant memorial near the parking area.

10. Oldsmar Flea Market

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For avid bargain seekers, the Oldsmar Flea Market is an outstanding destination within the city. Initiated in 1980 with self-storage sales, this expansive market is one of the largest along Florida’s Gulf Coast.

Visitors can find an array of goods, from fresh produce to furniture, apparel, used video games, tools, sporting equipment, plants, musical instruments, pet supplies, jewelry, and much more.

After experiencing a brief decline, the market underwent revitalization in 2018 when acquired by a St. Petersburg entrepreneur. Although a few booths remain vacant, the market was teeming with unique finds during my visit.

11. Tampa Bay Downs

From late November to early May, enjoy international-standard horse racing just minutes away at Tampa Bay Downs. This racetrack has been operational since 1926 and continues to host a variety of prestigious graded races.

Among the significant events are the Tampa Bay Derby and the Hillsborough Stakes, both taking place in March.

Similar to many racecourses in Florida, Tampa Bay Downs has introduced new gaming facilities including a 25-table poker room, ensuring vibrant year-round excitement.

I also appreciate the golf practice facility that opened here approximately twenty years ago, featuring a 40-station driving range, full-size putting green, dual chipping greens, PGA instructors, and a pro shop.

12. Oldsmar Trail

Oldsmar boasts a remarkable array of public parks, particularly along Tampa Bay. One way to access these parks is via the 10-mile paved Oldsmar Trail, which weaves through the city.

The trail commences at R.E. Olds Park and branches out in three directions: south toward Mobbly Bayou Beach Park, north to Cypress Forest Park, and northwest along the Lake Tarpon Canal to the Oldsmar Sports Complex.

This connected network comprises ten parks, providing an excellent opportunity for exploration via bicycle. The scenic views encompass the bay, the canal, and picturesque stands of bald cypress, live oaks, pines, and palms.

13. Tampa Bay Skating Academy

Source: Tampa Bay Skating Academy / Facebook

Ice skating may not be the first activity one associates with Florida’s Gulf Coast, but considering the region’s sunny and warm climate, the chill of a skating rink is often a welcome reprieve.

Tampa Bay Skating Academy features two ice surfaces and is part of a broader network of public rinks in the Tampa Bay area. Public skating sessions are offered daily at this facility.

The academy also hosts casual skates, pick-up hockey games, and freestyle sessions, alongside various programs primarily focused on teaching children to skate and training hockey players.

A multitude of youth and adult hockey teams utilize this facility, and spectators can enjoy games throughout the season.

14. Bicentennial Park

Source: City of Oldsmar, FL – Government / Facebook

This park is connected via a trail to Empower Adventures and the Mobbly Bayou Wilderness Preserve.

Bicentennial Park features a range of recreational amenities, including basketball, tennis, pickleball, and shuffleboard. Additionally, various exercise stations are available along the walking trail for those seeking physical activity.

The primary dog park in Oldsmar is also situated here, offering an area for fishing in the expansive reservoir located to the south. Notably, the playground looks newly built and boasts a wood chip surface.

15. AMC Woodlands Square 20

The AMC multiplex at Woodlands Square shopping center provides a premium cinematic experience, serving as a complete entertainment destination.

This venue prominently features an IMAX screen, which is undoubtedly the optimal choice for viewing major film releases. Another auditorium showcases a Dolby Cinema, presenting an ultra-vivid screen along with immersive Dolby Atmos audio.

All screens at AMC Woodlands Square 20 come equipped with reclining Lazyboy-style seating. I highly recommend selecting something captivating to watch, as these comfortable seats can easily lead to an unintended nap.