Explore the best rated trails in Greencastle, IN, whether you're looking for an easy walking trail or a bike trail like the Bicentennial Trail and 106th Street Path . With more than 59 trails covering 274 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.
As of July 2025, the path is not yet connected past 465. You can ride approximately six miles from the Monon near the State Fair Grounds (right turn, North of the grounds), and take it. It’s heavily shaded, very flat, and newly paved. It’s one of the most delightful trails in Indianapolis. There’s no really good option to get around 465 right now, but the area has been cleared for paving, so it’s just a matter of time before this connects. Until then, enjoy the out-and-back from the Monon, it’s an absolute delight!
Beautiful scenery and if you’re lucky you’ll see cows roaming the pastures! Nice trail with a good uphill climb in the middle. Ample parking at all trailheads along the route.
Road this today from trailhead in Colfax to Lebanon and most of the trail is enjoyable, but there’s parts where they really need to trim some of the branches and MOW along the sides of the trail!
We rode the whole length of the B&O today and we were glad to see that the two sections of the B&O are nearly connected. The trail is totally impassable at Country Club Road, and a couple of blocks in either direction of that intersection still need to be blacktopped, but otherwise the trail is pretty much done. For those unfamiliar with the B&O, it is a rail trail that varies from the very urban at the eastern terminus to very rural by the time you reach the western end. The trail runs right through the town of Speedway where you can find a couple of good breweries, a few other restaurants, ...and one enormous racetrack. The trail is in great shape, and connects to the rest of Indy's trail network.
Really love this trail, hometown trail and ride it 3-4 times a week. Only thing I wish is they would improve some of the paved trail that needs fixing (cracks/etc)
This trail was a very enjoyable ride. It was flat, pretty much straight and had many little spurs to get off to different parts of the area. I connects to the 3 mile long Buck Creek Trail and a very close connection to the Pleasant Run Trail (8 miles approx) so you can get a good amount of miles in with these trail connectors. They have a solar System Kiosk system with information about the Sun and the 8 closest planets (Mercury to Neptune). The trail itself looks new, especially in certain parts of it. It is well maintained and has good signage, although these have some gang signs on them. Some parts have absolutely no wind protection and other parts have solid trees on both sides of the trail. There is a little music area that you can play musical instruments and benches are plentiful.
Wow! This could be the worst trail I have ridden in years or ever. The trail rides from Ellenberger Park to Garfield Park. It was filthy with dirt on the trails, signage, while mostly helpful, was faded and/or had gang signs on them. I was ducking overhanging branches and pot holes/bumps for much of it along with riding through homeless tent city. There were a couple of intersections where it would've helped to have signage but as a first time rider, I was able to stick to the trail the whole time. This trail, in all honesty, has a lot of potential but it feels very neglected to say the least. Come on Indy, lets do better with this. It was so poor that I instead used roads instead of the trail to get back to my car.
This trail was top notch. It is a connection from Hornet Park to Bolton Park. Winding around a creek for much of the way, very new looking, clean with good signage. Parking on both ends of the trail. Probably best for running or walking due to the short distance but I must experience for trail lovers. It does not connect or have any near connections to any other trails.
This is one of the best trails in the central Indiana region but is in need of significant maintenance where pavement is buckling. For at least 2 miles from the trailhead in Lebanon toward Thorntown, the bumps are severe. Also, either side of Thorntown for about a mile each direction is just as bad. At the very least, the areas should be highlighted with paint. It has been this way for a couple of years now...does Boone County not care about the upkeep of this trail?
This trail runs right by our house, we use it daily for walking our dog, and getting to/from Main Street.
This trail goes along the beautiful White Lick creek and goes under the haunted train bridge. A must if you are biking!
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