Looking for the best trails around Sullivan?

Explore the best rated trails in Sullivan, IN, whether you're looking for an easy walking trail or a bike trail like the Bloomington Rail Trail and Clear Creek Trail (IN) . With more than 22 trails covering 94 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

Milwaukee Road Transportation Trailway

Decent trail

June, 2026 by rhenry21

Rode on a very hot muggy June morning, so as others have stated bring plenty of your own water. I did the whole trail, started at Williams Dam, felt the return trip back from Bedford was just slightly easier. Note that the trail goes under the 16th St., a major thoroughfare in Bedford, and that the many amenities visible on Google maps are not accessable from the trail. I would rate the scenery as just okay, not a destination trail but entirely worthwhile if in the area. And as always, many kudos to the local (I assume) volunteers for keeping up the trail. The end near Williams was a bit rough, possibly exacerbated by recent heavy rains, but the majority is very smooth.

Milwaukee Road Transportation Trailway

Decent trail

June, 2026 by rhenry21

Rode on a very hot muggy June morning, so as others have stated bring plenty of your own water. I did the whole trail, started at Williams Dam, felt the return trip back from Bedford was just slightly easier. Note that the trail goes under the 16th St., a major thoroughfare in Bedford, and that the many amenities visible on Google maps are not accessable from the trail. I would rate the scenery as just okay, not a destination trail but entirely worthwhile if in the area. And as always, many kudos to the local (I assume) volunteers for keeping up the trail. The end near Williams was a bit rough, possibly exacerbated by recent heavy rains, but the majority is very smooth.

National Road Heritage Trail (Terre Haute)

Great Trail

June, 2026 by maryjane711

I recently moved from a rural area in Parke County to Terre Haute.. I had no idea that the Parks and Recreation dept of Terre Haute had so many well kept trails and areas. The Heritage Trail is a phenomenal trail to bike. Mostly shaded and surrounded by nature this is truly a gem!!! The ride is very pleasant and enjoyable. From Blakey trailhead to Jones trailhead it is entirely paved. Much wildlife to be observed. It is approximately 7 miles round trip with numerous places to stop, rest and sit on a bench. To me this is HEAVEN!!!

Accordion

Milwaukee Road Transportation Trailway

nice trail

May, 2026 by cwilhoit51

It was a pleasant ride but bring your bug spray. Lots of standing water. Very few people on the trail.

Vandalia Trail

Rural Route

November, 2025 by cmrogers_tl

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.

Milwaukee Road Transportation Trailway

fun ride, but a few parts of the trail were. bit rough

October, 2025 by rmcfarland1535

We started at the dam and it was hard to find the start as there was no markings to say this was the start of the trail we found as we were about to leave over to the right. From there the trail was great for about 9 miles but then the gravel became so big we were having a bit of trouble riding. But all in all a fun little trail with some cool bluffs and neat bridges

Parke Community Rail Trail

starting in Rosedale Indiana

October, 2025 by w972dps96t

Covered bridge Gateway Trail in Rosedale, Indiana keep you updated

Lincoln Prairie Grass Trail

The segment east of Charleston is not paved. It's only a mile but if you are a trail completionist, be prepared for a rough ride for that mile or and back. Closer to a field road than a trail.Rest of the trail was perfect.

October, 2025 by scottthomasmartin

The segment east of Charleston is not paved. It's only a mile but if you are a trail completionist, be prepared for a rough ride for that mile or and back. Closer to a field road than a trail.Rest of the trail was perfect.

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.

Lincoln Prairie Grass Trail

TRAIL EXTENDED

September, 2025 by 56sugarcreek

The Lincoln Prairie Grass Trail pavement has been extended 6 blocks further west to the YMCA parking lot and a beautiful new park on 16th Street.

Milwaukee Road Transportation Trailway

Nice Milwaukee ride

August, 2025 by mike1318

First time on this gravel trail. Nice easy parking in Bedford. After leaving town there were a few areas getting work on after a washout. Once past those couple areas it was very beautiful shaded ride. Being a heavy user of Indianapolis trails, it is such a nice change to have peaceful country side to go through. Saw a couple of deer and a couple of bikers on, so I wasn’t worried about any stray cougars. Just kidding. Super enjoyable ride.

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.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.