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Gulfport Spur is a fun short addition to the Pinellas Trail, and amazingly is one of 30 side trails off of the main trail. You can see the list and locations on the Pinellas Country Trails Network map. The Gulfport Spur heads South from the Pinellas Trail just before Mile Marker 5 if you are traveling from downtown St Petersburg. The beginning of the trail is well marked with one of the large railroad-style signs used throughout the Pinellas Trail.

The Spur heads South around Boca Ciega High School and quickly ends after about a 1/2 mile. The Spur ends at 55th Street South, which is a great quiet side street to continue South on. After another 1/2 mile or so you’ll pass Tomlinson Park on the left. Tomlinson has a couple of baseball diamonds, and a small pond with a water feature and lots of wildlife.

Continue South until 55th Street South dead ends into Gulfport Boulevard South, and you’ll see the Northern edge of Jay P. Clymer Park right across the street. Directly across the street you’ll see a sign pointing towards the Gulfport waterfront. You can enter and ride through the park on the sidewalk, or ride down Beach Boulevard South which starts on the Northwest corner of the park.

Gulfport Waterfront Sign

Gulfport Waterfront Sign

Jay P. Clymer Park is worth a look. It’s roughly four blocks long and one block wide, but has 10 or 15 cool statues and art pieces throughout the park.

Jay P. Clymer Park Sign

Jay P. Clymer Park Sign

One of the statues is a giant rainbow wind chime. It’s cool looking, but not super musical.

Rainbow Wind Chime

Rainbow Wind Chime

After you leave the park, continue down Beach Boulevard South for a great selection of bars and restaurants. Gulfport also has some of the most interestingly decorated and painted small bungalows you’ll see in all of the Tampa Bay Area if you ride around a little on the side streets in the area.

At the very end of Beach Boulevard South you’ll see the Gulfport Casino building. The Casino has been repurposed into a 10,000 square foot ballroom and entertainment venue that is rented out for various events. As the name implies, it’s also the location of dance lessons and dance parties. Check out Gulfport Casino Weekly Dance Schedule for more information.

If you follow the sidewalk around the Casino to the back, there’s a large deck that overlooks Gulfport Harbor. Gulfport is a friendly anchoring spot and usually has dozens of large sailboats tied up across the harbor. There’s also a small statue of Morris the Casino Cat, who apparently was a famous resident of the casino from 1970 to 1985. Since our visit was in 2020, Morris was also featuring a cat-sized Corona mask.

Morris the Casino Cat

Morris the Casino Cat

The Gulfport Spur is definitely a worthwhile addition to a ride on the Pinellas Trail. It’s even better if you take time to eat at one of the excellent restaurants along Beach Boulevard South or Shore Boulevard South. We recommend Stella’s, especially if you’re on a breakfast ride.