Find the top rated horseback riding trails in Greencastle, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
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Rode this trail from the courthouse in Lebanon out almost to Colfax on April 12, 2026. As others have mentioned, there are some bumpy spots (roots upheaving the trail) near Thorntown, so just slow down there. And there's a half-mile stretch where it's a bit overgrown, but still easily passable. Overall, it a great trail and bit of a hidden gem. Very wide in some places; more-so than the B&O trail. Rode a total of 25 miles and just saw a handful of people. There are only a few road crossings and most of those are out in the country, with no traffic. We stopped at Klooz Brewz afterward for some nourishment. It was great!
The trail has a few spots where it’s kind of smooth but otherwise the concrete is severely heaved. Might be OK for someone to walk on, but not really suitable for biking. If you live in the area fine but don’t take a trip for this. Disappointing. There’s one nice stretch right before the bridge but that’s about it.
We ride this trail a lot but always dread the section passing through Thorntown. The bumps in the trail are one thing as not cheap to repave but the overhanging honeysuckle is easily remedied. We often start on the south side of Thorntown and ride to Lebanon just to avoid this bone rattling stretch.
The newest addition to the trail nearly makes it a full circle. The CCT is one of the state’s best biking trails. It weaves it around the country side through some wooded parts of the area. The terrain can be a challenge as it is a fairly steep grade to tackle on a hot and humid day. All I all, it’s a great trail to ride.
Visited Indianapolis the week before Thanksgiving 2025 for a conference and rode the trail from Carmel to Sheridan and back. It was a warm and sunny November day, which brought out lots of trail users. Downtown Carmel is a delightful place to stop and walk around - show respect for other users and ride slowly through town. Further north the trail opens up with longer distances between road crossings, and far fewer groups walking or jogging. I turned around just before the end of the trail in Sheridan. I see opportunity to some enterprising business owners to develop more options for trail users in Sheridan, but during my ride I stopped at the Speedway just off the trail at Main Street to refuel and take a break. I'm looking forward to some day riding the length of the trail into downtown Indy.
Beautiful trail ride on 11/15/25! It runs along beside a horse trail. You will see lots of farms, cows, chickens and horses and cornfields, loved it, from Amo to Greencastle .Would have give it a 5 star if there would have been bathrooms at the end of the trail.
I love this trail. It’s maintained very well, and I feel generally safe as a woman going through the wooded areas alone
The Thorntown parks and recreation dept needs to step it up a notch on this section of the trail. The bumps are so significant it jars my teeth and nearly throws me off the bike. Most of the rest of the trail from Lebanon to Colfax is just fine.
There was some work done on the 1 1/2 mile section just out of Lebanon, which is now relatively smooth. Thorntown needs to fix that one or two sections. The one just after the street cross-over bridge coming into Thorntown and then the most horrible section from Thorntown to the bridge crossing over the river. That section is bone jarring.
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