The Airport Just Extended the Trail Outside Bear's Paw's Gate. Here's Where It Goes Now.

Anyone who has lived at Bear's Paw for more than a season knows the gravel pull-off just past the gatehouse isn't there for visitors. It's where neighbors leave their cars before a walk, where the dog gets its evening loop, where a bike ride starts before the heat sets in. The trail that begins at that pull-off is the Gordon River Greenway, and for years it has done exactly one thing well: it went out, and it came back. You walked toward the airport fence, the pavement ran out, and you turned around.

That changed earlier this year. The Naples Airport Authority's Board of Commissioners funded an extension that connects the Greenway's old terminus, near the Collier Mosquito Control District building, to two places it never reached before: the airport's public Observation Deck and the City of Naples' Baker Park. The same project paid for removing invasive vegetation, restoring worn sections of pathway, and rejuvenating a stagnant pond near North Road. None of it came from a county parks bond or a city tax line. It came out of an airport's own operating budget, the same one funded by fuel sales and hangar rentals rather than property taxes, because the land the new connector crosses belongs to the airport, and the airport has been a partner in this stretch of trail since 1989.

That funding detail matters more than it sounds like it should. Most public trail improvements in Naples move on a parks department calendar, tied to bond cycles and capital budgets that get discussed at commission meetings months in advance. This one moved on the airport's own schedule, because the airport already maintains close to two miles of trail, boardwalk, and bridge on its own property at no cost to city or county residents. When the airport decides a stretch of its own land needs work, it doesn't wait for a countywide vote. That's why this extension showed up with less fanfare than a project this size usually gets, and why a resident who hasn't walked past the old dead end in a while might not know the loop out of Bear's Paw's gate now goes somewhere new.

Where the New Endpoints Actually Lead

The Observation Deck sits at 1825 North Road, a raised, wheelchair-accessible platform built in 2012 where you can watch aircraft on approach to Runway 5 while speakers pipe in live chatter from the control tower. It's a strange, oddly peaceful place to end a walk, and it just got its own refresh. Work completed in March 2026 included pressure washing, minor structural repairs, restroom improvements, and a fresh stain on the deck surfaces, handled by St. Lazarus Painting. That's the modest version. Later this year the airport expects to finalize designs for a larger rebuild at the same site, one that would add permanent ADA-compliant covered seating, a playground, a fitness area, restrooms, and static model aircraft on display. Permitting and construction are expected in 2027, so this year's refresh is the placeholder before the real project breaks ground.

The other new endpoint, Baker Park, is a fifteen-acre park at 100 Riverside Circle, reached across the Gordon River by the Blair Foundation pedestrian bridge. It opened in October 2019, named for donors Jay and Patty Baker, and it packs in more than most fifteen-acre parks manage: a thirty-four-foot landscaped knoll with a spiral path to the top, a kayak launch onto the Gordon River for anyone with a city permit, a splash pad, a café building, and an outdoor performance space. If you've driven past it on Goodlette-Frank Road without ever walking in from the Greenway side, the bridge is the part you were missing. Before this year's extension, getting from the Bear's Paw trailhead to Baker Park meant leaving the trail and driving around. Now it's one continuous walk.

What You'll Actually Pass Along the Way

The stretch between the two new endpoints runs through six native plant communities, threading boardwalk over mangrove and open pavement past pine flatwoods. Regulars report alligators, bobcats, otters, herons, egrets, anhingas, woodpeckers, ibis, and the occasional bald eagle, which is a wider range of wildlife than most trails inside city limits can claim. The bridge crossings have wide bump-outs built specifically for fishing or for stopping to watch the water, and the Gordon River itself is the same waterway that runs along Bear's Paw's own southern boundary. Members with dock or lift space at the community marina are already looking at this river every time they take a boat out. The Greenway just gives you a way to see more of it on foot.

A few practical notes worth knowing before you go:

• The trail is open daily from 6:30 a.m. to 10 p.m., free to enter, and lit along its length for evening walks.
• Leashed dogs are welcome the entire route, including on the Baker Park side.
• Kayak or canoe launch access at Baker Park requires a city permit if you plan to leave your boat there, though a same-day launch doesn't.
• The Observation Deck side dead-ends at Port Avenue if you keep walking past the deck itself, which is worth knowing before you commit to a round trip in the heat.

The Season to Actually Use It

September in Naples is not walking weather for most people, and that's fine. The extension isn't going anywhere, and neither is the bigger Observation Deck rebuild, which won't break ground until 2027 at the earliest. What's worth doing now, before the first cool front of the season, is scouting the new connector on a bike so you know the route before the trail gets busy with snowbirds in December. The gravel pull-off outside the gate hasn't changed. What's on the other end of that walk has.

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