Looking for the best trails around Paoli?

Explore the best rated trails in Paoli, 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 19 trails covering 124 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

Patoka Lake Bike Trails

Great trails!

June, 2026 by sarakreilein

We biked every one of these trails and some of the adjoining campgrounds too! We had an awesome time — the highlight was taking in the amazing views of Patoka Lake on the trail leading down to the beach area. The trails are well-paved and offer plenty of forest shade mixed with sunshine. Road crossings are well-marked and minimal. All of these trails are out-and-back (not loops) which helps you get even more mileage in. Of course with it being southern Indiana - it is HILLY, which helps the trails stay interesting! We biked these in the Summer but would love to come back in the Fall as it will be even more beautiful. 10/10 highly recommend! recommend!

Jasper Riverwalk

Peaceful and Varied

June, 2026 by sarakreilein

A beautiful and well maintained path winding through thick forest to the north and aside farmland to the south. Riding over the steel bridge at the Old City Mill and seeing the railroad/old industrial district to the north are highlights. There are restrooms at Dave Buehler Plaza and many benches and picnic tables along the path. Easy access to restaurants and downtown Jasper. Jasper Riverwalk connects with the greater Jasper trail system at its north end and can be taken all the way around to the Jasper Parklands, about 9 miles in total paved path (not including the Parklands paths).

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.

Accordion

Louisville Loop

Floyd’s Fork section

March, 2026 by westrichdave

My wife and I rode the Floyd’s Fork section today. The weather was beautiful and the trail was pretty and fun! Some parts are in the trees and bushes and you feel like you’ve gotten away from the world. The trail itself is well maintained. We came across many people who were walking, jogging and biking. If you are a biker and moving a little too fast, you will need to be careful on the bends so you don’t get in a “tight spot” with other people! we truly enjoyed riding on this section of the loop.

Monon South Trail

Love the Trail

November, 2025 by lphillipsblack

Hi I run and Bike. Water fountains open at Pekin trail head. Partial crushed rock and paved. Awesome 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

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.

Ohio River Greenway

Great ride!

July, 2025 by edjanetravel

Indiana has done a beautiful job with this trail. Could use real restrooms on New Albany end but the port a pots were fairly clean.

Karst Farm Greenway

Great Trail

June, 2025 by cameronscott343

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.

Monon South Trail

Good start to the Monon South

May, 2025 by gwczpykkxp

As of May 2025 you can ride about 10 miles uninterrupted from Deam Lake to Pekin. The trail is paved through 5 towns (Borden, Pekin, Salem, Orleans, Mitchell). Restroom facilities are being built in a couple of those towns. It’s crushed lime except in the towns. Very enjoyable trail.

Louisville Loop

Riverwalk section is awful

April, 2025 by tod.hanson

We rode the Riverwalk section and the Big Four Bridge. The bridge was great, the Riverwalk was not. It is true they had major flooding about 3 weeks ago and, understandably, this was not yet fully remediated. But even in unaffected areas the majority of the trail goes through dilapidated inner city and industrial sections with only minimal and unmaintained landscaping, hardscaping, or other park amenities. If you want a much better southern Riverwalk trail experience, go to Chattanooga TN or Columbus GA.

Big Four Bridge

Salvaged the Louisville Loop experience

April, 2025 by tod.hanson

We crossed the Big Four Bridge while riding the River Walk portion of the Louisville Loop trail. The bridge was way better than the trail.

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