Explore the best rated trails in Hilton Head Island, SC, whether you're looking for an easy walking trail or a bike trail like the Hilton Head Island Pathways and JF Gregory Park Trail . With more than 11 trails covering 84 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
My wife and I took a three week bike trip in late Feb 2025, and happy we started with Spanish Moss. Nice flat, wide trail with different views of the area including neighborhoods, moss covered woods, water views and some commercial areas. There were a few busy road crossings, but nothing to worry about. Lot’s of historic sites along the route including the train station. And of course, lot’s of Spanish moss along the way, which for us northerners is quite the treat. Add this one to your list.
This trail is one of the best. Entire trail was concrete and very smooth. Passed by Marine base with Great timing seeing 2 launches and one return trip of military jets.
Fantastic trail system. Excellent maps and sign on trail, easy riding for the whole family
Rode it from the entrance gate at Fort Pulaski. First three miles were in great condition. It is hard packed what looks like crushed gravel. Great views on one side of the river, but it runs parallel to the highway a few yards away. The heavy traffic noise detracted some from the experience. After 3 miles it separates from the trail, but in this section it is poorly maintained. There are some parts where it is down to single track. Large sections that are covered in washed over reeds. The tires on our tandem bike sunk in making it like pedaling through loos sand.
Really nice trail to ride. We did have some trouble finding the trailhead but other than that, we enjoyed the ride.
Good flat trail that is well maintained. Many cyclists and folks walking pets in the later afternoon. Enjoyed my ride time but giving only a 4 star due to many road crossings that can be dicey depending on time of day even with cross signals.
Fairly flat concrete path. Well maintained. Had some things to stop and read about historic buildings that surrounded the path. Great scenery along the way
Fairly flat concrete path. Well maintained. Had some things to stop and read about historic buildings that surrounded the path. Great scenery along the way
Horseflies were hungry this morning. Trail was very nice
First time running the loop. For the most part trail was well shaded and nice scenery. Three miles of a nice walk or bike ride. Will definitely be making this my running trial for training.
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