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 Pennsy Trail (IN) and White River Greenway (Carmel) . With more than 59 trails covering 280 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

Big 4 Trail (Lebanon to Colfax)

Thorntown to the Sugar Creek Bridge

October, 2025 by tayers1

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.

Parke Community Rail Trail

starting in Rosedale Indiana

October, 2025 by w972dps96t

Covered bridge Gateway Trail in Rosedale, Indiana keep you updated

B&O Trail

trail completion

September, 2025 by eileen.gasper

Grand opening 9/29 It was very well done

Accordion

Riley Spur Trail

Newly Paved Trail

September, 2025 by neumann_tl

Had a wonderful bike ride with the family. It was a hot day, but the shaded trail made for a delightful time. We parked at S Llama St where there is a small gravel parking lot, unloaded the bikes and rode the 1.6 miles to the bridge just East of S Canal St. that crosses a creek. The scenery in summer was great and the newly updated bridge was well done. An added bonus was all the trail crossings over the streets were stamped concrete that resembled the rail crossings that used to be there.

Monon Trail

very nice trail

September, 2025 by ltlarrow

loved riding this trail (except for the crowds on the trail for Carmel Days). My only complaint was the poorly placed trail marker where the trail made a hard right turn north of Carmel near Rt 32. The bathroom facility at 96th Street was outstanding.

Big 4 Trail (Lebanon to Colfax)

trail is great in sections

September, 2025 by jtkoehler2

Colfax to Sugar Creek nice and smooth, from Suram Plant rd to Lebanon nice and smooth! The section maintained by Thorntown has trees over growing the trail and many many bumps . The trail needs a repaving. Thorntown section runs from Sugar Creek to Suram plant rd. I called the Thorntown,s clerks office (only open Tuesday) and reported the problem. They said trees removal will be next week Issue back by September

Monon Trail

We parked at the 69th Street Trailhead. We went north & it was a shady and a scenic ride. Carmel had restaurants next to the trail. Lots of walkers, cycles, & dogs. Very nice trail.

September, 2025 by sicnj2al

We parked at the 69th Street Trailhead. We went north & it was a shady and a scenic ride. Carmel had restaurants next to the trail. Lots of walkers, cycles, & dogs. Very nice trail.

Covington Circle Trail

update on length

September, 2025 by stonebraker1985

The final section of this trail along the wabash river on the west side was officially completed first week of August…the trail is now a complete “circle” and just under 7 miles in length.

Big 4 Trail (Lebanon to Colfax)

Enjoyable Ride

August, 2025 by goldfussjennifer

My husband and I rode this trail on 8-22-25. We thoroughly enjoyed ourselves and thought the trail was relatively well maintained. Some have complained about branches and rough surfaces but we did not find it bad at all. We are used to riding country roads in much worse conditions. We rode to Colfax and stopped to enjoy a meal at Pizza King. I highly recommend this stop! It had a small town friendliness and great service. We enjoyed a sub sandwich, salad, breadsticks, and milkshake. The breadsticks were outstanding as well as the handcrafted shakes- so many flavors from which to choose. We split the buckeye shake and it was delicious!

Monon Trail

LOVED IT!

August, 2025 by zap26

On my way from PA to WI I decided to stop in Indianapolis, IN. I decided to ride the Monon Trail to the Cultural Trail in downtown, to the Canal Walk and reverse. I absolutely loved the ride, enjoyed riding through the city, and really liked all the murals and art as I was riding. As I was riding south and getting closer to downtown Indianapolis, there were a lot of road crossings, however I will say this was one of the most courteous places to bike, almost every car stopped to let bikers cross. If I ever come back to Indianapolis I would definitely ride this trail again. It is in one of my top 5 trails. Definitely worth doing if you are in Indianapolis.

Wabashiki Trail

Noisy traffic but enjoyable

July, 2025 by sacrawf

Noisy traffic but nice views from the boardwalk. Extend your walking buy going south through Fairbanks park on the east side of the Wabash bridge.

Montezuma B&O Walking Bridge

Montezuma Wabash Bridge

July, 2025 by sacrawf

I’ve walked this multiple times, both alone and with grandkids. Parking is excellent and there are picnic table and benches at the site and on the Wabash bridge itself. The high sides of the first portion of the former railroad bridge obstructs views but it opens up to steel trestle for scenic river views. Beyond the bridge the trail is enjoyable with tributory on the left and woods/fields on the right. Unfortunately the trail ends at the active railroad tracks and a picnic table. Plans to extend are apparently underway. Train watching is fun at the terminus. Make it a real walk by walking through the nearby parks, downtown, and stopping at the Tasty Freeze for great ice cream.

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