North of Fruitville Road, the paved path runs up the east side of Circus Boulevard and through Circus Nature Trail Park. A few hundred yards short of the Bobby Jones Golf Club entrance, it crosses the boulevard to the west, passes the Gillespie par-3 course, and crosses back to the east. From there it continues to the Bobby Jones complex. Your Observer described it this way in May: you can ride it today, but first you have to make that crossing twice and handle a mix of surfaces and cracked pavement that isn't built for heavy use.
That half mile is now the Legacy Trail's rough edge, and in 2026 it got much easier to reach. Sarasota County finished the connector from the trail's South Beneva Road crossing, across Fruitville Road, to Circus Trail. Just south of that, the county opened the trail's first separate walking path. The north end got its most polished stretch and its most direct link to the least polished one in the same year, and Fruitville Road is where the two meet.
How Far North the Trail Goes Now
The Legacy Trail is longer than many people's picture of it. When it opened in 2008, it ran 10 miles north from the Venice Train Depot into Palmer Ranch. Your Observer reported in April that it now reaches just north of Payne Park in downtown Sarasota, and the long-term goal is Sarasota-Bradenton International Airport.
Two pieces of older construction are also finished. FDOT lists the Clark Road and Bee Ridge Road overpasses as complete, with an estimated cost of $13.2 million. Riders who planned around those crossings for years can use the bridges now.
Riding north from the Fairgrounds area, the trail now goes like this:
- Pompano Trailhead, 601 S. Pompano Ave. It sits just south of the Sarasota County Fairgrounds and is where the county held the March ribbon cutting.
- Shade Avenue to Beneva Road. This is the new split section, with a walking strip alongside the main trail.
- South Beneva Road crossing north to Fruitville Road. This is the county's connector, finished this year.
- Circus Trail, Fruitville Road to Bobby Jones. The City's older path with the double crossing of Circus Boulevard, ending near the Bobby Jones entrance.
Stops one through three are the newest construction on the north end. Stop four is the oldest pavement on the route and has had the least work.
South of Fruitville, Walkers Have Their Own Lane
On March 31, the county opened a 1.5-mile walking path that runs alongside the trail between Shade Avenue and Beneva Road. It is six feet of asphalt, with a strip of sod between it and the main trail. Bikes, scooters, and inline skaters stay on the main trail. Walkers and runners use the new strip. As of an April 30 update, the county's project page lists construction as complete.
The split went in here because of crowding. The trail gets more than 600,000 users a year, according to Shawn Yeager, the county's interim parks director, as reported by Your Observer. The same report says the county designed the sections between downtown and Palmer Ranch extra wide so its busiest stretches could be split later. Commissioners approved that widening plan in 2023.
"The trail is the gift that just gets bigger, it's better, it's safer; it just continues to be an amazing amenity for Sarasota County."
That was County Commission Chair Ron Cutsinger at the ribbon cutting, quoted by Your Observer.
The 1.5 miles is only the first phase of a 4.18-mile widening project. Here is how Your Observer breaks down the funding:
| Funding source | Amount |
|---|---|
| Grants | $400,000 |
| Grant-matching money | $497,000 |
| Private donations | $320,000 |
| Impact fee revenue | $117,000 |
The grant came from the Florida Department of Environmental Protection's Recreational Trails Program. Friends of the Legacy Trail and the Sarasota-Manatee Bicycle Club put up matching money. The county says it designed the whole project first and is building it in phases. It has not published dates for the phases after this one. Today, the split covers Shade Avenue to Beneva Road only. Past Beneva, everyone shares one trail again.
North of Fruitville, the Plan Runs to 2029
The City's plan to rebuild Circus Trail is still in design, and construction is targeted for 2028 to 2029.
On May 4, the Sarasota City Commission voted unanimously to sign a design agreement with the Florida Department of Transportation for Circus Trail. FDOT and the Sarasota-Manatee Metropolitan Planning Organization have granted $1.1 million for the project, which covers design of just over half a mile of trail. The main change is that the whole route would stay on the east side of Circus Boulevard, so trail users would no longer cross it.
Alvimarie Corales, the City's capital projects manager, gave commissioners the timeline, according to Your Observer. The City has funded design through the 30% stage, and that stage is expected to finish this fall. Final design would follow and take about one to one and a half years. Construction would come in FDOT's 2028-2029 fiscal year. As of this fall, the City's own project page lists 30% design as underway and says construction timing will be set once design is done.
Once it's built, the trail would enter Bobby Jones at the main entrance off Circus Boulevard. It would pass the clubhouse and practice area, then run through the nature park. It would stop just short of Sarasota County's 17th Street Regional Park on purpose. Corales explained why:
"It would end before the 17th Street Park, because the idea is that once it's built, we can partner with Sarasota County. Then Sarasota County can help us determine where they want the crossing."
The City's larger goal is a continuous route from the Legacy Trail at Beneva Road to Bobby Jones, then 17th Street Regional Park, and eventually Nathan Benderson Park. The City is also building toward downtown. Its Payne Park and Alderman multi-use trail project, which its project page lists as under construction, would connect the Legacy Trail toward downtown neighborhoods. From there, the Ringling Trail would continue toward the bayfront, St. Armands, and Lido Key.
Until that work is done, the stretch from Fruitville to Bobby Jones is a ride for patient people. Expect the double crossing at Circus Boulevard and uneven pavement before the complex entrance.
This Fall's Events Use Both Ends of the Trail
The fall calendar from Friends of the Legacy Trail spreads out along the whole corridor, from Nokomis to Payne Park.
Taco Tuesday, Nokomis Community Park, 234 Nippino Trail E. The first one of the season is tomorrow, October 13, from 5 to 8 p.m. The next is November 10, same hours and same place. The Friends group describes it as an evening of local taco food trucks, held the second Tuesday of every month from October through March.
The 50th CycleFest, November 15, 8100 Main St., Lakewood Ranch. The Sarasota-Manatee Bicycle Club organizes it. The Friends listing says the routes support local bicycle charities. The ride doesn't use the trail, but it is on the Friends calendar.
The 5th Annual Legacy Trail Ultra, November 22, Payne Park. It's a free 60K out-and-back sponsored by the Manasota Track Club. Runners head south to Legacy Park in Venice and come back. The race starts near the trail's downtown end and turns around in Venice.
If you want to start somewhere other than downtown, the county's trail brochure lists Culverhouse Nature Park, 7301 McIntosh Road, as one of the official trailheads.
The Rules for a Trail That's Only Split in One Place
The split only runs between Shade Avenue and Beneva Road, so the rest of the trail is still shared. That's where the county's rules matter most. The current trail brochure, dated September 2026, lists these:
- The speed limit is 15 mph.
- Warn people before you pass them.
- Pass on the left, in single file, leaving three feet of room.
- If you're on a bike, yield to other trail users.
- Don't stop where you block the trail.
- E-bikes are allowed if they have working pedals. Other motorized vehicles are not.
Those rules apply on the cracked, narrower path north of Fruitville too. The Circus Boulevard crossings call for the same care, especially on fall event weekends when more people are out.
Kelly Rosenberg has watched Sarasota change for more than 30 years, and the trail now reaches a long list of mainland neighborhoods. If you'd like to know how close a home is to a Legacy Trail entrance, or what the Circus Trail work could mean for streets near Bobby Jones, Kelly Rosenberg is glad to talk it through. Request a personalized home valuation or call Kelly for a market consultation.
