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Routes
Running Trails
United States
Florida
Pinellas County

Oldsmar

The best running trails around Oldsmar

4.0

(1)

560

runners

56

runs

Jogging around Oldsmar offers a variety of routes through parklands and along multi-use trails. The region is characterized by its relatively flat terrain, often featuring paved paths and green spaces suitable for running. Many routes traverse local parks, providing access to natural settings and waterfront views. These running trails offer options for different distances and experiences within the Oldsmar area.

Best jogging routes around Oldsmar

  • The most popular jogging route is John Chestnut Senior Park loop, a 3.8 miles (6.2 km) trail that takes about 40 minutes to complete. This route offers a scenic loop through parkland.
  • Another top favourite among local runners is Oldsmar Trail, a moderate 8.9 miles (14.3 km) path. This trail provides a longer running experience along a multi-use pathway.
  • Local runners also love the Running loop from Phillippe Parkway & Pinellas Avenue, a 4.6 miles (7.4 km) trail leading through residential areas and green spaces, often completed in about 45 minutes.
  • Jogging around Oldsmar is defined by park loops, multi-use paths, and urban greenways. The network offers options for different ability levels, from shorter park runs to longer trail segments.
  • The routes in Oldsmar are highly rated by the komoot community with an average score of 4.0 stars from over 1 review. More than 500 runners have used komoot to explore Oldsmar's varied terrain.

Last updated: April 25, 2026

5

runners

#1.

John Chestnut Senior Park loop

6.16km

00:38

0m

0m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

14.3km

01:28

0m

0m

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Oldsmar

Hiking around Oldsmar

Cycling around Oldsmar

Road Cycling Routes around Oldsmar

Tips from the Community

Joseph
March 22, 2025, Safety Harbor Marina Pier

safe - bike lanes or greenways

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Philippe Park has all of the usual park amenities such as picnic area, a playground, and trails. However, this park also has a lot of history discover. Not only is it the oldest park in the county it is also home to the Tocobaga Temple Mound, which is the largest remaining Native American mound remaining in the Tampa area.

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mtm05005
December 9, 2024, Philippe Park

Philippe Park is a 92-acre park and is the oldest park in Pinellas County. The park is named after Odet Philippe, who is responsible for bringing the grapefruit to Florida. Within the park is a Tocobaga Indian mound, as well as several other Tocobaga remnants.

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The Oldsmar Trail is a wide paved trail that doesn't have a ton of trail markers but is still pretty easy to follow. This section of trail follows the canal way and is one of the quieter sections of trail, but be careful at the road crossings (especially the highway crossing with a stoplight). If you are just looking for a trail to cruise on next to the water, this is a good one to try out.

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Safety Harbor Marina includes two parks: Veterans Memorial Marina Park & Safety Harbor Waterfront Park. Veterans Park has a pier that juts into the bay, and Safety Harbor Park features a series of bridges and boardwalks that look out onto the water and city from a different perspective.

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Safety Harbor Marina includes two parks: Veterans Memorial Marina Park & Safety Harbor Waterfront Park. Veterans Park has a pier that juts into the bay, and Safety Harbor Park features a series of bridges and boardwalks that look out onto the water and city from a different perspective.

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The Oldsmar Trail is a wide paved trail that doesn't have a ton of trail markers but is still pretty easy to follow. This section of trail follows the canal way and is one of the quieter sections of trail, but be careful at the road crossings (especially the highway crossing with a stoplight). If you are just looking for a trail to stroll on next to the water, this is a good one to try out.

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The Oldsmar Trail's southern end is at Bicentennial Park, which includes a handful of interconnecting boggy lakes and reservoirs. There are a few different paths and picnic areas in this park, and there is parking so that you can start your hike from this end as well.

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Frequently Asked Questions

Are there easy running routes suitable for beginners in Oldsmar?

Yes, Oldsmar offers several easy running routes perfect for beginners. Many of the trails are relatively flat and paved, making them accessible. While specific beginner routes aren't detailed, the region has 9 easy tours out of 50 total, indicating good options for those starting out. Look for routes within local parks for a gentler experience.

Where can I find longer running trails in Oldsmar?

For a longer running experience, the Oldsmar Trail is an excellent choice, stretching about 8.9 miles (14.3 km). Another option for a more challenging, longer run is the Philippe Park – Safety Harbor Marina Pier loop from Enterprise Road East & Harbor Woods Drive, which covers nearly 10 miles (15.8 km).

Are there family-friendly running paths in Oldsmar?

Many of Oldsmar's running paths are suitable for families, especially those within parks. The relatively flat terrain and multi-use trails make them safe and enjoyable for all ages. Routes like the John Chestnut Senior Park loop are popular for their scenic parkland setting, offering a pleasant environment for a family jog or walk.

Can I bring my dog on the running trails in Oldsmar?

Most parks and multi-use trails in Oldsmar are dog-friendly, provided your pet is on a leash and you clean up after them. It's always a good idea to check specific park regulations before heading out. Trails through green spaces and parklands are generally welcoming to leashed dogs.

Are there circular running routes available in Oldsmar?

Yes, Oldsmar features several excellent circular running routes. The John Chestnut Senior Park loop is a popular example, offering a scenic 3.8-mile (6.2 km) circuit. Another well-liked option is the Running loop from Phillippe Parkway & Pinellas Avenue, which is about 4.6 miles (7.4 km) long.

Is parking available at the trailheads in Oldsmar?

Parking is generally available at the main access points for Oldsmar's running trails, especially at local parks. For instance, parks like John Chestnut Senior Park and Philippe Park typically offer dedicated parking facilities for visitors. It's advisable to check specific park websites for detailed parking information.

What kind of scenery can I expect on Oldsmar's running routes?

Oldsmar's running routes offer a mix of scenery, primarily featuring parklands, green spaces, and multi-use paths. You can expect waterfront views along some sections, especially near Tampa Bay, and routes that traverse through natural settings. The region's flat terrain often means pleasant, open vistas.

Are there any interesting landmarks or attractions near the running trails?

Yes, several running routes pass by or are close to interesting landmarks. For example, the area around Philippe Park features the Tocobaga Temple Mound at Philippe Park, a significant historical site. You might also encounter the Safety Harbor Marina Pier on longer routes, offering scenic bay views. The Lake Tarpon at John Chestnut Park is another beautiful spot to see.

What do other runners enjoy most about jogging in Oldsmar?

The running routes in Oldsmar are highly rated by the komoot community, with an average score of 4.0 stars. Runners often praise the well-maintained multi-use paths, the scenic parkland settings, and the variety of distances available. The relatively flat terrain is also frequently mentioned as a positive for enjoyable runs.

What is the best time of year for running in Oldsmar?

The best time of year for running in Oldsmar is typically during the cooler, drier months from late fall through spring (roughly November to April). During this period, temperatures are more moderate, and humidity is lower, making for more comfortable runs. Summers can be very hot and humid, with frequent afternoon thunderstorms.

Are there options for running on rainy days in Oldsmar?

While most running in Oldsmar is outdoors, the paved multi-use trails can still be used on lighter rainy days, though caution is advised for slippery surfaces. For heavier rain or thunderstorms, indoor alternatives would be necessary, as there are no covered outdoor running tracks in the area. Always check weather forecasts, especially during the summer rainy season.

How many running routes are available in Oldsmar?

Komoot currently lists over 50 running routes around Oldsmar, offering a wide variety of options for different preferences and fitness levels. These include routes through parklands, along multi-use trails, and urban greenways.

Can I find routes that offer views of lakes or water bodies?

Absolutely. Several routes in and around Oldsmar provide beautiful views of lakes and other water bodies. For instance, the Lake Tarpon at John Chestnut Park is a prominent feature along some trails. You can also find scenic spots like the R.E. Olds Park Waterfront, offering pleasant views during your run.

Are there any shorter running loops for a quick workout?

Yes, Oldsmar has several shorter running loops ideal for a quick workout. The Pond at Cooper's Bayou Park loop from Safety Harbor is a moderate 3.1-mile (5.1 km) route that can be completed in under 30 minutes, offering a refreshing run through park scenery.

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