Highland Trails and Maps

47 Reviews

Looking for the best trails around Highland?

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

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  • Length
Activities
Length
Surfaces
Type
16 Results
Activities
Length
Surfaces
Type

Big 4 Trail (Lebanon to Thorntown)

9.5 mi
State: IN
Asphalt, Crushed Stone

Brown Boulevard Trail

2.2 mi
State: IN
Asphalt

Collett Park Pathway

1.4 mi
State: IN
Concrete

Covington Circle Trail

4.4 mi
State: IN
Asphalt

Dobbs Trail

0.8 mi
State: IN
Asphalt

Fairbanks Park Trail

0.6 mi
State: IN
Concrete

Hulman Street Trail

3.7 mi
State: IN
Concrete

Indiana Veterans Memorial Mile

1 mi
State: IN
Asphalt

Kickapoo Rail Trail

6.7 mi
State: IL
Gravel

Lafayette Linear Park

1.1 mi
State: IN
Asphalt

Lincoln Prairie Grass Trail

12.9 mi
State: IL
Asphalt, Crushed Stone

Rosedale South Trail

0.6 mi
State: IN
Asphalt

Sugar Creek Trail

3.7 mi
State: IN
Asphalt, Crushed Stone

Vandalia Trail

16 mi
State: IN
Asphalt, Crushed Stone, Dirt, Grass, Gravel

Wabashiki Trail

7 mi
State: IN
Asphalt, Crushed Stone, Dirt
Trail Image Trail Name States Length Surface Rating
The Big 4 Rail Trail is a developing trail route across Boone County that will one day span 50 miles. Currently, two disconnected segments of the rail-trail are open. The name is a reference to the...
IN 9.5 mi Asphalt, Crushed Stone
The Brown Boulevard Trail offers students from Terre Haute North Vigo High School a safe route to the Indiana State University Stadium to catch a game. The 2-mile trail also connects to the National...
IN 2.2 mi Asphalt
The Collett Park Pathway begins on the northern edge of the Indiana State University campus, where it connects to the National Road Heritage Trail, a proposed border-to-border route stretching between...
IN 1.4 mi Concrete
Covington Circle Trail provides a partial loop around Covington in northwestern Indiana, offering views of farmland, wetlands, and small wooded creeks. Future plans call for completing the circle...
IN 4.4 mi Asphalt
Although less than 1 mile long, the Dobbs Trail offers an important connection between two of Terre Haute's most popular parks, Deming and Dobbs. It follows Poplar Drive, a tree-lined residential...
IN 0.8 mi Asphalt
Although less than 1 mile long, there are plenty of reasons to hit the Fairbanks Park Trail in western Indiana's Terre Haute. The tree-lined pathway winds along the banks of the Wabash River through...
IN 0.6 mi Concrete
The Hulman Street Trail follows its namesake roadway through residential and commercial areas of Terre Haute, passing Farrington Grove Elementary School along the way. At its western end, the trail...
IN 3.7 mi Concrete
The unique Indiana Veterans Memorial Mile circles Indiana State University's football stadium in the shape of the state. Along the way, fitness stations add to your walking or biking routine. At...
IN 1 mi Asphalt
The first 6.7-mile section of the Kickapoo Rail Trail in eastern Illinois opened in August 2017. Paralleling U.S. 150, the Champaign County rail-trail runs from Urbana east to St. Joseph along the...
IL 6.7 mi Gravel
The Lafayette Linear Park is a paved trail on the southern side of Lafayette, Indiana. The trail occupies a rail corridor once used by the Cleveland, Cincinnati, Chicago and St. Louis Railway...
IN 1.1 mi Asphalt
The Lincoln Prairie Grass Trail runs 12 miles, much of the way along an old railroad right-of-way between County Highway 2 east of Charleston and the ball fields at 10th Street in Mattoon; an...
IL 12.9 mi Asphalt, Crushed Stone
The Terre Haute segment of the National Road Heritage Trail runs for nearly 7 miles between the west end of Indiana State University campus downtown and Chamberlain Road behind Mewhinney Cemetery just...
IN 7 mi Asphalt
The Rosedale South Trail offers a paved, tree-lined route along the former Pennsy Railroad in the western Indiana community of Rosedale. It begins on the south side of town and travels just over a...
IN 0.6 mi Asphalt
The Sugar Creek Trail meanders on the southwestern outskirts of Crawfordsville through suburban back yards, wooded parks and cultivated fields. It follows part of an old Cleveland, Cincinnati, Chicago...
IN 3.7 mi Asphalt, Crushed Stone
The Vandalia Trail is the longest open component of the National Road Heritage Trail, a proposed border-to-border trail stretching between Terre Haute and Richmond, Indiana, a span of more than 150...
IN 16 mi Asphalt, Crushed Stone, Dirt, Grass, Gravel
The Wabashiki Trail sits on the traces the perimeter of theĀ  Wabashiki Fish and Wildlife Area, leaving travelers with the dual experience of nature and suburbia on either side. Great for wildlife...
IN 7 mi Asphalt, Crushed Stone, Dirt

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Trails by activity

Fairbanks Park Trail

IN - 0.6 miles

Although less than 1 mile long, there are plenty of reasons to hit the Fairbanks Park Trail in western Indiana's Terre Haute. The tree-lined pathway winds along the banks of the Wabash River through...

Vandalia Trail

IN - 16 miles

The Vandalia Trail is the longest open component of the National Road Heritage Trail, a proposed border-to-border trail stretching between Terre Haute and Richmond, Indiana, a span of more than 150...

Lincoln Prairie Grass Trail

IL - 12.9 miles

The Lincoln Prairie Grass Trail runs 12 miles, much of the way along an old railroad right-of-way between County Highway 2 east of Charleston and the ball fields at 10th Street in Mattoon; an...

Wabashiki Trail

IN - 7 miles

The Wabashiki Trail sits on the traces the perimeter of the  Wabashiki Fish and Wildlife Area, leaving travelers with the dual experience of nature and suburbia on either side. Great for wildlife...

Accordion

Sugar Creek Trail

IN - 3.7 miles

The Sugar Creek Trail meanders on the southwestern outskirts of Crawfordsville through suburban back yards, wooded parks and cultivated fields. It follows part of an old Cleveland, Cincinnati, Chicago...

Hulman Street Trail

IN - 3.7 miles

The Hulman Street Trail follows its namesake roadway through residential and commercial areas of Terre Haute, passing Farrington Grove Elementary School along the way. At its western end, the trail...

Collett Park Pathway

IN - 1.4 miles

The Collett Park Pathway begins on the northern edge of the Indiana State University campus, where it connects to the National Road Heritage Trail, a proposed border-to-border route stretching between...

Covington Circle Trail

IN - 4.4 miles

Covington Circle Trail provides a partial loop around Covington in northwestern Indiana, offering views of farmland, wetlands, and small wooded creeks. Future plans call for completing the circle...

Brown Boulevard Trail

IN - 2.2 miles

The Brown Boulevard Trail offers students from Terre Haute North Vigo High School a safe route to the Indiana State University Stadium to catch a game. The 2-mile trail also connects to the National...

Big 4 Trail (Lebanon to Thorntown)

IN - 9.5 miles

The Big 4 Rail Trail is a developing trail route across Boone County that will one day span 50 miles. Currently, two disconnected segments of the rail-trail are open. The name is a reference to the...

Kickapoo Rail Trail

IL - 6.7 miles

The first 6.7-mile section of the Kickapoo Rail Trail in eastern Illinois opened in August 2017. Paralleling U.S. 150, the Champaign County rail-trail runs from Urbana east to St. Joseph along the...

Lafayette Linear Park

IN - 1.1 miles

The Lafayette Linear Park is a paved trail on the southern side of Lafayette, Indiana. The trail occupies a rail corridor once used by the Cleveland, Cincinnati, Chicago and St. Louis Railway...

National Road Heritage Trail (Terre Haute)

IN - 7 miles

The Terre Haute segment of the National Road Heritage Trail runs for nearly 7 miles between the west end of Indiana State University campus downtown and Chamberlain Road behind Mewhinney Cemetery just...

Dobbs Trail

IN - 0.8 miles

Although less than 1 mile long, the Dobbs Trail offers an important connection between two of Terre Haute's most popular parks, Deming and Dobbs. It follows Poplar Drive, a tree-lined residential...

Indiana Veterans Memorial Mile

IN - 1 miles

The unique Indiana Veterans Memorial Mile circles Indiana State University's football stadium in the shape of the state. Along the way, fitness stations add to your walking or biking routine. At...

Rosedale South Trail

IN - 0.6 miles

The Rosedale South Trail offers a paved, tree-lined route along the former Pennsy Railroad in the western Indiana community of Rosedale. It begins on the south side of town and travels just over a...

Collett Park Pathway

IN - 1.4 miles

The Collett Park Pathway begins on the northern edge of the Indiana State University campus, where it connects to the National Road Heritage Trail, a proposed border-to-border route stretching between...

Dobbs Trail

IN - 0.8 miles

Although less than 1 mile long, the Dobbs Trail offers an important connection between two of Terre Haute's most popular parks, Deming and Dobbs. It follows Poplar Drive, a tree-lined residential...

Hulman Street Trail

IN - 3.7 miles

The Hulman Street Trail follows its namesake roadway through residential and commercial areas of Terre Haute, passing Farrington Grove Elementary School along the way. At its western end, the trail...

Brown Boulevard Trail

IN - 2.2 miles

The Brown Boulevard Trail offers students from Terre Haute North Vigo High School a safe route to the Indiana State University Stadium to catch a game. The 2-mile trail also connects to the National...

Accordion

Indiana Veterans Memorial Mile

IN - 1 miles

The unique Indiana Veterans Memorial Mile circles Indiana State University's football stadium in the shape of the state. Along the way, fitness stations add to your walking or biking routine. At...

Lafayette Linear Park

IN - 1.1 miles

The Lafayette Linear Park is a paved trail on the southern side of Lafayette, Indiana. The trail occupies a rail corridor once used by the Cleveland, Cincinnati, Chicago and St. Louis Railway...

Kickapoo Rail Trail

IL - 6.7 miles

The first 6.7-mile section of the Kickapoo Rail Trail in eastern Illinois opened in August 2017. Paralleling U.S. 150, the Champaign County rail-trail runs from Urbana east to St. Joseph along the...

Covington Circle Trail

IN - 4.4 miles

Covington Circle Trail provides a partial loop around Covington in northwestern Indiana, offering views of farmland, wetlands, and small wooded creeks. Future plans call for completing the circle...

National Road Heritage Trail (Terre Haute)

IN - 7 miles

The Terre Haute segment of the National Road Heritage Trail runs for nearly 7 miles between the west end of Indiana State University campus downtown and Chamberlain Road behind Mewhinney Cemetery just...

Wabashiki Trail

IN - 7 miles

The Wabashiki Trail sits on the traces the perimeter of the  Wabashiki Fish and Wildlife Area, leaving travelers with the dual experience of nature and suburbia on either side. Great for wildlife...

Fairbanks Park Trail

IN - 0.6 miles

Although less than 1 mile long, there are plenty of reasons to hit the Fairbanks Park Trail in western Indiana's Terre Haute. The tree-lined pathway winds along the banks of the Wabash River through...

Lincoln Prairie Grass Trail

IL - 12.9 miles

The Lincoln Prairie Grass Trail runs 12 miles, much of the way along an old railroad right-of-way between County Highway 2 east of Charleston and the ball fields at 10th Street in Mattoon; an...

Sugar Creek Trail

IN - 3.7 miles

The Sugar Creek Trail meanders on the southwestern outskirts of Crawfordsville through suburban back yards, wooded parks and cultivated fields. It follows part of an old Cleveland, Cincinnati, Chicago...

Rosedale South Trail

IN - 0.6 miles

The Rosedale South Trail offers a paved, tree-lined route along the former Pennsy Railroad in the western Indiana community of Rosedale. It begins on the south side of town and travels just over a...

Vandalia Trail

IN - 16 miles

The Vandalia Trail is the longest open component of the National Road Heritage Trail, a proposed border-to-border trail stretching between Terre Haute and Richmond, Indiana, a span of more than 150...

Big 4 Trail (Lebanon to Thorntown)

IN - 9.5 miles

The Big 4 Rail Trail is a developing trail route across Boone County that will one day span 50 miles. Currently, two disconnected segments of the rail-trail are open. The name is a reference to the...

Kickapoo Rail Trail

IL - 6.7 miles

The first 6.7-mile section of the Kickapoo Rail Trail in eastern Illinois opened in August 2017. Paralleling U.S. 150, the Champaign County rail-trail runs from Urbana east to St. Joseph along the...

Wabashiki Trail

IN - 7 miles

The Wabashiki Trail sits on the traces the perimeter of the  Wabashiki Fish and Wildlife Area, leaving travelers with the dual experience of nature and suburbia on either side. Great for wildlife...

Fairbanks Park Trail

IN - 0.6 miles

Although less than 1 mile long, there are plenty of reasons to hit the Fairbanks Park Trail in western Indiana's Terre Haute. The tree-lined pathway winds along the banks of the Wabash River through...

Covington Circle Trail

IN - 4.4 miles

Covington Circle Trail provides a partial loop around Covington in northwestern Indiana, offering views of farmland, wetlands, and small wooded creeks. Future plans call for completing the circle...

Accordion

Indiana Veterans Memorial Mile

IN - 1 miles

The unique Indiana Veterans Memorial Mile circles Indiana State University's football stadium in the shape of the state. Along the way, fitness stations add to your walking or biking routine. At...

Lafayette Linear Park

IN - 1.1 miles

The Lafayette Linear Park is a paved trail on the southern side of Lafayette, Indiana. The trail occupies a rail corridor once used by the Cleveland, Cincinnati, Chicago and St. Louis Railway...

Rosedale South Trail

IN - 0.6 miles

The Rosedale South Trail offers a paved, tree-lined route along the former Pennsy Railroad in the western Indiana community of Rosedale. It begins on the south side of town and travels just over a...

Vandalia Trail

IN - 16 miles

The Vandalia Trail is the longest open component of the National Road Heritage Trail, a proposed border-to-border trail stretching between Terre Haute and Richmond, Indiana, a span of more than 150...

Collett Park Pathway

IN - 1.4 miles

The Collett Park Pathway begins on the northern edge of the Indiana State University campus, where it connects to the National Road Heritage Trail, a proposed border-to-border route stretching between...

Big 4 Trail (Lebanon to Thorntown)

IN - 9.5 miles

The Big 4 Rail Trail is a developing trail route across Boone County that will one day span 50 miles. Currently, two disconnected segments of the rail-trail are open. The name is a reference to the...

Hulman Street Trail

IN - 3.7 miles

The Hulman Street Trail follows its namesake roadway through residential and commercial areas of Terre Haute, passing Farrington Grove Elementary School along the way. At its western end, the trail...

Lincoln Prairie Grass Trail

IL - 12.9 miles

The Lincoln Prairie Grass Trail runs 12 miles, much of the way along an old railroad right-of-way between County Highway 2 east of Charleston and the ball fields at 10th Street in Mattoon; an...

Dobbs Trail

IN - 0.8 miles

Although less than 1 mile long, the Dobbs Trail offers an important connection between two of Terre Haute's most popular parks, Deming and Dobbs. It follows Poplar Drive, a tree-lined residential...

Brown Boulevard Trail

IN - 2.2 miles

The Brown Boulevard Trail offers students from Terre Haute North Vigo High School a safe route to the Indiana State University Stadium to catch a game. The 2-mile trail also connects to the National...

Sugar Creek Trail

IN - 3.7 miles

The Sugar Creek Trail meanders on the southwestern outskirts of Crawfordsville through suburban back yards, wooded parks and cultivated fields. It follows part of an old Cleveland, Cincinnati, Chicago...

National Road Heritage Trail (Terre Haute)

IN - 7 miles

The Terre Haute segment of the National Road Heritage Trail runs for nearly 7 miles between the west end of Indiana State University campus downtown and Chamberlain Road behind Mewhinney Cemetery just...

Recent Trail Reviews

Big 4 Trail (Lebanon to Thorntown)

nice trail

September, 2017 by jtkoehler2

couldn't get to the trail head in thorntown the road was closed. So we got on off pearl st and franklin south of SR 47. the trail to start was paved. As soon as we got out of thorntown, the pavement was a little rough. As we headed south east it varied from a little rough to some lose gravel. The lose gravel ended about a 1/2 mile north of Hazelrigg rd. 300 n. it was new smooth pavement. We rode south about another mile and turned around. We ran across another rider who said the new pavement goes for a way the it was back to what was north of Hazelrigg. ( not as rough) He said when you get nearer to Lebanon it goes back to smooth pavement. We are working up the 20 mile round trip Thorntown to Lebanon. We did half today ( hazelrigg). (10 miles) We are both in our 60's and having ridden much over the past 15 years.

Vandalia Trail

Excellent!

August, 2017 by drreneeke

What a beautiful trail! Newly paved from Amo for a few miles before hitting the gravel path. We did the full 16 and was hoping there would be a restaurant to stop at once we hit Coatsville but there was nothing convenient at the end of the trail. Be sure to bring plenty of water and snacks. Beautiful scenery. We saw butterflies and hummingbirds throughout most of the trail. Very peaceful.

National Road Heritage Trail (Terre Haute)

sorry

July, 2017 by liechtyvix

I wanted to say east side is best

Accordion

National Road Heritage Trail (Terre Haute)

great asset to terre haute

July, 2017 by liechtyvix

grandson and I ride it often, little creek park is a good place for a picnic break. rose hulman is like a post card. access to cemetery for some hills and history, access to hawthorn park adds some miles. go west is best.

Big 4 Trail (Lebanon to Thorntown)

Lovely on big tires

October, 2016 by fintone

The canopy of hardwoods, the beauty of farmland and the peace of solitude all await you here. Probably need something bigger than 23mm tires though.

I rode this trail end to end on a fat tire bike and it was a little slice of heaven.

Lincoln Prairie Grass Trail

Much improved

August, 2016 by bristol1031

I first rode this trail several years ago and was not impressed: the surface was full of washouts and 4 wheeler ruts. However it now seems to be better maintained. The easternmost section is the best, a narrow corridor with lots of wildflowers and birds. As you get closer to Mattoon the trail opens up and there is no protection from the sun and wind. For a nice bit of shade take the spur into the Douglas Hart Nature Center.

Big 4 Trail (Lebanon to Thorntown)

Big 4

August, 2016 by ericcriswell

Overall a nice peaceful trail
Went for a 10 mile ride (5 out and back) starting at Lebanon trail head behind Menards. First 2.5 miles are newly paved and we'll maintained, after that I would recommend off road bike. My remaining 2.5 miles traveling north were a mix of old grumbles of asphalt,fine limestone, and grass. One small section about a city block long was deep small stone, the kind that doesn't compact and you just sink in. That all being said it was a nice ride with typical Indiana flat land views of fields.

Vandalia Trail

First Time Trail Cyclist

July, 2016 by jmcnabb_tl

I live within five miles of the Amo trailhead but until this week I have never been on the trail. What a pleasant change in perspective. I know the roads and communities along the trail in western Hendricks county but never at such a delightful pace. Coming back soon!

Big 4 Trail (Lebanon to Thorntown)

Rough pavement south of Thorntown

June, 2016 by doug526

I would not recommend this trail for road bikes. With a mountain bike or all-terrain tires you might be fine. If you start at Thorntown and head south, just after you pass the bridge the trail turns into very rough pavement and gravel, not crushed stone. The trail is in definite need of rehabilitation for road bike use. I have not attempted starting at the Lebanon end of the trail, so I don't know how conditions are closer to that town.

National Road Heritage Trail (Terre Haute)

Bataan Death March

May, 2016 by halls26

We used this trail for our Bataan Death March and it was perfect. There were plenty of access points for water/medic stations. One of the best trails I have been on.

Sugar Creek Trail

Beautiful ride/run through the Indiana country!

November, 2015 by jbat770

I live 10 minutes from this trail and love to use it! it's very scenic and mostly paved. Many indigenous trees, wildlife, and of course beautiful sugar creek. Come visit!

Vandalia Trail

Hidden Jewel

October, 2015 by indyivy

I rode the portion of the trail from Amo to Fillmore and back on Sunday, October 18, 2015. Very surprised to find that in two and a half hours of pedaling, I encountered only one other cyclist, along with two pedestrians and two women on horseback. This was a picture perfect October day with temperatures in the low seventies! I have to agree with the other reviewer who remarked that the unpaved surface seems to scare riders away. It shouldn't, it's a very firm-packed surface for most of the way. Obviously, it takes more effort and a bit longer to ride than a paved surface, but that only adds to its charm.

Of special interest to me as a railroad buff was the Interurban Depot in Amo, built by the T.H.I. & E. (Terre Haute, Indianapolis and Eastern Traction Company) in 1907, and now on the National Register of Historic Places. It is basically located at the trail head in Amo, and is a well restored gem that is now used as the Amo Reading Room. Unfortunately it's only open from 6:00-8:00 p.m. Tuesdays and Thursdays, and for two hours on the first Saturday of each month. The T.H.I. & E. only operated from 1907 to 1931, and apparently shared the roadbed with the Vandalia Railroad. The town of Amo, pop. Approx. 420, is a dlight and has more of an old west feel than you would expect to find in a town only about 20 miles west of Indianapolis. The ancient Amo General Store is open, and doubles as a pizza parlor.

The ride itself is mostly rural, but every grain elevator and silo I passed was bustling with activity, as the cornfields were being harvested, taking full advantage of the dry, sunny weather.

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