Greencastle Trails and Maps

329 Reviews



Looking for the best trails around Greencastle?

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 57 trails covering 260 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.

Recent Trail Reviews

Sugar Creek Trail (IN)

Excellent Venue

October, 2024 by jwelch4

On a business trip I was able to ride two evenings. Beautiful early fall foliage along the way. Asphalt pavement is smooth and a short gravel run along the old railway. Beautiful crossing of Sugar creek on a wooden bridge structure is a sure place to stop and enjoy the view. Well maintained. Multiple sightings of deer, squirrels, and geese. I will definitely return and bring a road bike or mountain bike.

Big 4 Trail (Lebanon to Colfax)

Colfax to Lebanon

October, 2024 by q4prh9v7k7

What a great trail. Mostly wooded. All hard surface. Extremely enjoyable!

B&O Trail

Michigan St. End

September, 2024 by currykimberly395

I rode the shorter portion and found it very different from the west end. The maintenance was absent with bushes growing onto the trail. Trash was also on, and right next to trail. It was a bit disappointing to see the difference in how each section is cared for.

Accordion

Indianapolis Cultural Trail

An energizing experience

August, 2024 by tarheeltim76

I hit the Indianapolis Cultural Trail around dusk, dog tired after a long drive from North Carolina. What a delight! The trail is broad, flat and easy to follow thanks to the colored pavers. The sections flanking the canal were stunning at nightfall and well lit after dark. Parks, restaurants, monuments, museums and the zoo are all easily accessible. It was an energizing experience to bike this trail. Highly recommended.

Monon Trail

Round trip 54 miles

July, 2024 by tjmodd

Rode the full length of this trail round trip. It’s well maintained and used by many people. Great surface for road bikes. Lots of places along the trail to stop and eat. Nice bridges. Lots of road crossings but many people were courteous and would stop for bike crossing, runners, and walkers. Equal mix of shade and sun. This is a great trail.

Big 4 Trail (Whitestown)

July 5 Whitestown to Zionsville

July, 2024 by kevin.gruneisen

Rode the trail from Whitestown to Zionsville today. Got a little wet but it’s great that the trail has been extended to connect the two cities. The round trip was about 14 miles with very little elevation change. I would say about 75% is covered with shade. The complete path is asphalt. There is no parking at the Whitestown trail head. See parking info in the trail details for the parking area, which is right on the trail. There is a good brewery in Whitestown, Moontown Brewery for a post ride beverage. We skipped that part today as we were pretty soaked from the afternoon rain. Enjoy.

Big 4 Trail (Lebanon to Colfax)

June 30 - Thorntown to Colfax

July, 2024 by kevin.gruneisen

Rode the Big 4, parking at Thorntown, riding to Colfax and back. The ride was roughly 6 miles one way with limited elevation. The asphalt path is good, a little bumpy out of Thorntown but smooths out for a nice ride. The path was cluttered with vegetation following the storms the day before. This part of the path is well covered providing good shade and wind block. Be sure to notice the birdhouses tucked into the trees as you near Colfax. Enjoy.

White River Wapahani Trail

Beautiful, but …

June, 2024 by dmarkwillis

This would-be beautiful trail is ideally situated and features lovely vistas of Indianapolis, views of the White River and a curvy paved path through a shady, wooded landscape. Sadly, a good portion of it is marred by countless homeless encampments and the resulting undisposed of trash. A sad reflection on our city and its leadership. The trail was also dangerously scattered with river debris and thick loose sand in several low spots. Ride for curiosity’s sake, but with caution.

Big 4 Trail (Lebanon to Colfax)

Nice Solitary Ride!

June, 2024 by gregmclochlin

I’m an EBiker, and LOVE the solitude! Smooth, paved trail with very short paths invaded by fairly low tree roots. I stopped for lunch at STOOKLEYS which I HIGHLY recommend! Yum! I started in Colfax, at the trail end, and went almost to Lebanon, then turned back, (out and back.) BEAUTIFUL DAY!!

Pennsy Trail (IN)

After the monon and nickel plate trail this is the 3rd best in the region

June, 2024 by soluschristus01

After the monon and nickel plate trail this is the 3rd best in the region

B&O Trail

B&O Trail

June, 2024 by kevin.gruneisen

2024 - we live 1 mile from the trail and can get to it pretty easy. The ride is great. All asphalt and in great shape. Several main roads have to be crossed but all have signal lights to help. Tilden is no longer the end of the trail. There is another ~ 3 miles of new asphalt west of Tilden. A new parking lot was added at 300/900. Enjoy. It’s or go to for weekly rides.

Vandalia Trail

Vandalia

June, 2024 by kevin.gruneisen

June 10, 2024 Starting @ Amo, Indiana is a nice trail head with water and clean bathrooms. Heading West in Hendricks County is a well maintained asphalt path. I do t remember any breaks or bad spots like other trails where tree roots have caused the asphalt to buckle. The ride west takes you out of Hendricks County and into Putnam County. The ride (about 4 miles) is tree lined and well protected. When you cross the county line the path switches to crushed rock, maybe limestone. Regardless, it is easy to navigate. I’ve ridden a lot of trails outside of Chicago and am used to this type of path. In 3.5 miles is Filmore and turned to head back. Great ride. Highly recommended.

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