Westport, IN Walking Trails and Maps

114 Reviews

Looking for the best Walking trails around Westport?

Find the top rated walking trails in Westport, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
22 Results
Activities
Length
Surfaces
Type

Blue River Trail (Shelbyville)

3.5 mi
State: IN
Asphalt, Concrete

Franciscan Trail

2.2 mi
State: IN
Asphalt

Franklin Greenway Trail

3.4 mi
State: IN
Asphalt

Heritage Trail of Madison

2 mi
State: IN
Asphalt, Dirt, Grass, Gravel

Indianapolis Cultural Trail

10.5 mi
State: IN
Asphalt

Landersdale Trail

1.5 mi
State: IN
Asphalt

Pennsy Trail (IN)

14.5 mi
State: IN
Asphalt

Shaker Trace Trail

7.8 mi
State: OH
Asphalt

Tracy Trail

1.5 mi
State: IN
Asphalt

Whitewater Canal Trail

11 mi
State: IN
Crushed Stone, Gravel

Columbus People Trail

15.7 mi
State: IN
Asphalt, Concrete

National Road Heritage Trail (Henry County)

8.2 mi
State: IN
Crushed Stone

Progress Parkway Trail

4 mi
State: IN
Asphalt

Pleasant Run Trail

6.9 mi
State: IN
Asphalt

Shirley Heritage Trail

1.1 mi
State: IN
Asphalt

Woolly Bear Parkway Trail

1.4 mi
State: IN
Grass, Gravel

Amos Road Trail

1 mi
State: IN
Asphalt

Aero Parkway Bicycle Trail

2.3 mi
State: KY
Asphalt
Accordion

Nickel Plate Trail (Connersville)

0.75 mi
State: IN
Asphalt

Polly Grimshaw Trail

0.65 mi
State: IN
Concrete
Trail Image Trail Name States Length Surface Rating
Crossing from one end of Shelbyville to the other, the Blue River Trail provides a safe way for residents to walk or bike to a number of parks whilst enjoying the proximity to the city's beloved...
IN 3.5 mi Asphalt, Concrete
The Greendale segment runs 1 mile between Walnut Street and Hollywood Boulevard at Eads Parkway, paralleling Eads Parkway/US 50 on the east side. There's a short gap (0.6 mile) in the trail between...
IN 5.4 mi Asphalt
The Franciscan Trail provides over 2 miles of walking and biking routes through Beech Grove, part of the Indianapolis metro area. The 12-foot wide, two-lane asphalt path allows residents to connect...
IN 2.2 mi Asphalt
The Franklin Greenway Trail (also known as the Franklin Historic Trail) is 3.4 miles of paths threading through Franklin’s parks while connecting community amenities such as schools, community centers...
IN 3.4 mi Asphalt
The Heritage Trail of Madison connects the downtown of Madison, Indiana, with its steep hilltop section. Begin your journey at the intersection of Vaughn Drive and Vernon Street along the Ohio River....
IN 2 mi Asphalt, Dirt, Grass, Gravel
Located in the heart of vibrant downtown Indianapolis, the Indianapolis Cultural Trail is an ideal way to experience all the city has to offer. The trail links five cultural districts flush with...
IN 10.5 mi Asphalt
The Landersdale Trail is a 10-foot-wide, paved asphalt path that runs adjacent to and parallel to Landersdale Road in northern Morgan County. The western end of the path connects the fringe of the...
IN 1.5 mi Asphalt
Overview The Pennsy Trail is currently open in two main segments. About the Route The western segment leaves off from the eastern side of Indianapolis, linking the Irvington neighborhood with...
IN 14.5 mi Asphalt
The Shaker Trace Trail forms a loop around Miami Whitewater Forest, the largest county-run park in Hamilton County. The fully-accessible, paved trail runs for nearly 8 miles through the park’s...
OH 7.8 mi Asphalt
The Tracy Trail is a short suburban greenway in the town of Greenwood. The trail runs north–south between Summerfield Park and just north of Woodman Park near Southwest Elementary School. The open...
IN 1.5 mi Asphalt
The White River Greenway brings residents of Martinsville to the river, for rest, for relaxation and for education. The asphalt trail begins at Old Town Waverly Park, and follows the river's course...
IN 2 mi Asphalt
Running along a former rail bed, the Whitewater Canal Trail parallels the Whitewater Canal as it takes hikers and cyclists through the heart of the Whitewater River Valley in Franklin County.  The...
IN 11 mi Crushed Stone, Gravel
The Columbus People Trail offers an easy and convenient way for residents in this small Indiana city to get around by bike or on foot. The network comprises more than 15 miles of sidewalks, on-road...
IN 15.7 mi Asphalt, Concrete
The Henry County segment of the National Road Heritage Trail runs for 8 miles over two segments. One runs from Big Blue River in Raysville east to SR 3 west of Dunreith (4 miles); the other between S...
IN 8.2 mi Crushed Stone
The Progress Parkway Trail is a flat, hardtop shared-use path running along the east edge of Shelbyville, Indiana. Despite its name, the trail actually starts along Lee Boulevard, on the east edge of...
IN 4 mi Asphalt
The Pleasant Run Trail travels along both the creek and road of the same name as it courses through eastern Indianapolis, although the trail is located on sidewalks in certain areas. In the north, the...
IN 6.9 mi Asphalt
The Shirley Heritage Trail provides easy access to recreational opportunities while celebrating the history of the Town of Shirley.  At about a mile long, the trail runs east along South Railroad...
IN 1.1 mi Asphalt
The Woolly Bear Parkway Trail is on the former Pennsylvania rail corridor that starts in Kennard and extends west for 1.4 miles. The rustic trail is mostly grass with a gravel base, and lined with...
IN 1.4 mi Grass, Gravel
The Amos Road Trail contributes a mile to Shelbyville's growing trail network. The trail is located in the southern reaches of the city. It is a flat shared-use path on the side of Amos Road, taking...
IN 1 mi Asphalt
This shared use path may only be 2.3 miles long, but it is appreciated by residents in Florence as a place to exercise. It travels alongside Aero Parkway, which borders the Cincinnati/ Northern...
KY 2.3 mi Asphalt
Accordion
Connersville's Nickel Plate Trail is situated in rural eastern Indiana, not far from the state's border with Ohio. Its trailhead is located at the intersection of 32nd Street and Park Road and, from...
IN 0.75 mi Asphalt
Bloomington’s Polly Grimshaw Trail is a short rail-with-trail that provides a crucial link from the city’s east side to State Route 45, close to Indiana University. The trail runs between apartments...
IN 0.65 mi Concrete

Recent Trail Reviews

Whitewater Canal Trail

Very pleasant trail

March, 2025 by gsdavidson

The trail was in great shape, especially for early Spring . The only issue was some gravel wash out from the tracks near Metamora; wider tires are helpful. Lots to look at on the canal. Pleased to see restrooms which are always welcome. Lots of food available when open.

Indianapolis Cultural Trail

It’s been extended

January, 2025 by slcurts

The northwest corner of the trail shown on this map now extends along Indiana Avenue and along 10th Street, and also there’s a new stretch along South Street.

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.

Accordion

Shaker Trace Trail

One of my absolute favorite trails to skate!

August, 2024 by rgombosch

I find it can be really hard to find a good trail for inline skating, but this one is one of my absolute favorites! If I want to push myself for a workout, I could usually finish the loop in an hour. Of course there are some tricky spots like when crossing the roads or the giant hills at the beginning and end, but this still remains as one of my top trails for roller blading. It’s a great workout, is nice and long, and has beautiful changing scenery throughout the entire trail.

National Road Heritage Trail (Henry County)

finding the trailhead

July, 2024 by prr7443

Lovely trail, once I found it. Phone was a little confused. Could use better signage in the area to direct people to the parking area, which was well hidden. And very few locals seemed to have ever even heard of it. Perhaps TrailLink could provide more detailed directions/location?

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

Woolly Bear Parkway Trail

mosquito heaven

May, 2024 by branden86401

Trail was all grass and tall at some points. Me and my 2 kids got bit up super bad though by mosquitoes. Spiders webs and mosquitoes are horrible.

Franklin Greenway Trail

Great!

May, 2024 by jasonahyer

Great little well-maintained bike/walk path!

Pennsy Trail (IN)

Awesome trail

April, 2024 by leanneklamb

Way less traffic than the Monon trail, had a great time riding my ride here.

Pennsy Trail (IN)

quad or roller skating - perfect

March, 2024 by keepingthepiece

I thoroughly entire skating this trail. There are multiple sports to park and enter the trail. The trail has some uneven places, but is mostly an easy and relatively flat trail. I entered at mile marker 1, skated to the end, turned around and started to the other end, then back to my car. My total was 5.16 miles.

Shirley Heritage Trail

short and sweet

March, 2024 by luv_mlb25

I ran this trail back in September 2023. I planned a trip to Indianapolis but knew I needed to fit in a short run along the way. This was easily accessible off I70 and was just long enough to get a quick mile or two in for the day. Nice pit stop after sitting in a car. The trail was decent, flat, and wide open. No shade, but honestly it's not long enough to really worry about being in the shade for a lengthy period of time. The trail runs along a main road and then circles around the city park. There are benches and plenty of parking. I am not sure of the amenities around town, but there was a gas station. Small town trail but another one marked off the list.

Tracy Trail

skating trail for the win

February, 2024 by keepingthepiece

The trail isn’t smooth, and you have to cross multiple roads, but it’s nice having this trail in town along a little winding creek with a couple playgrounds along the way. It starts at Summerfield Park where there’s plenty of parking.

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