4.4
(15)
292
riders
40
rides
Road cycling around Highland features a diverse landscape, characterized by a mix of flat greenways, lake-side paths, and moderate elevation changes. The region offers routes that traverse former railway lines, providing accessible and generally low-gradient cycling experiences. Riders can expect to encounter varied terrain, from urban park connectors to longer loops around natural features. The network of routes caters to different skill levels, with options for both easy and moderate rides.
Last updated: November 7, 2026
3.0
(1)
16
riders
41.9km
01:53
80m
80m
Embark on an easy road cycling journey through northwest Indiana and eastern Illinois with the Erie Lackawanna and Pennsy Greenway Loop. This 26.0-mile (41.9 km) route, featuring a gentle 249-foot…
2
riders
63.3km
02:44
60m
60m

75.6km
03:16
190m
190m
59.2km
02:31
170m
170m
23
riders
71.3km
02:53
120m
120m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Popular around Highland
The Oak Savannah Trail climbs in an elegant arch as the truss bridge spans Main Street. The bridge is enclosed on all sides and is open only to trail users.
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Pennsy Greenway is a 14.5-mile rails-to-trails paved path following the former Penn Central Railway. It currently connects Munster, Indiana, to Lansing, Illinois.
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Whihala Beach County Park boasts over a mile of sandy Lake Michigan shoreline.
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Cedar Lake is a peaceful, 760-acre lake surrounded by forests and wetlands.
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Escape into serene wilderness at Ivan Gatlin Nature Preserve, overlooking the winding Kankakee River in Illinois.
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This trail runs 17.7 miles (28.5 km) from Hammond to Crown Point. It follows the former Erie Lackawanna Railway which closed was abandoned in 1986. You cycle through green countryside and several towns. It's paved and smooth – a great place to ride!
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This trail leads 17.8 miles (28.6 km) through lovely nature. The paved trail traces the former Port Branch of the Elgin, Joliet and Eastern Railway. Highlights en route include the Indiana Dunes, oak savanna ecosystems and Oak Ridge Prairie Park. In Griffith, the trail joins the Erie Lackawanna Trail.
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Road cycling around Highland offers a diverse landscape, primarily characterized by flat greenways, lake-side paths, and moderate elevation changes. Many routes utilize former railway lines, providing accessible and generally low-gradient cycling experiences. You'll encounter varied terrain, from urban park connectors to longer loops around natural features.
There are over 35 road cycling routes available in Highland, catering to various skill levels. This includes 16 easy routes and 20 moderate routes, ensuring options for both casual riders and those seeking a bit more challenge.
Yes, Highland offers several easy road cycling routes perfect for beginners. A popular choice is the Erie Lackawanna and Pennsy Greenway Loop, a 26.0-mile (41.9 km) trail that primarily follows paved greenways, offering a smooth and enjoyable ride.
For those seeking a moderate challenge, the Cedar Lake and Erie Lackawanna Trail Loop is a great option. This 47.0-mile (75.6 km) path combines trail sections with scenic views around Cedar Lake. Another excellent choice is the Whihala Beach County Park loop, a 39.3-mile (63.3 km) trail leading through park areas and along the waterfront.
The road cycling routes in Highland are highly rated by the komoot community, with an average score of 4.6 stars from over 12 reviews. Cyclists often praise the well-maintained greenway paths, the scenic lake-side trails, and the variety of park loops available.
Yes, many of the routes in Highland are designed as loops, offering convenient circular rides. Examples include the Erie Lackawanna and Pennsy Greenway Loop and the Cedar Lake and Erie Lackawanna Trail Loop, allowing you to start and finish at the same point.
While cycling in Highland, you can explore various natural and man-made features. Highlights include the Erie-Lackawanna Rail-Trail, the Oak Savannah Trail, and the Illinois Pennsy Greenway. You might also cross the Calumet Avenue Pedestrian Bridge or ride near the Chase Street Conservation Area.
The duration of road cycling routes in Highland varies depending on the route and your pace. For example, the easy Erie Lackawanna and Pennsy Greenway Loop typically takes about 1 hour 53 minutes, while the moderate Cedar Lake and Erie Lackawanna Trail Loop can take around 3 hours 16 minutes.
Yes, many routes are designed to offer varied scenery. The Erie Lackawanna Trail and Cedar Lake Loop is a great example, combining sections of the Erie Lackawanna Trail with picturesque views around Cedar Lake, offering a 36.8-mile (59.2 km) ride.
Road biking in Highland is generally characterized by well-maintained greenway paths and lake-side trails. The routes are typically low-gradient, making for smooth rides. Conditions are usually favorable for cycling, especially during pleasant weather, allowing for an enjoyable experience across the varied terrain.
For a shorter, easy ride, consider the Pennsy Greenway – Pennsy Greenway loop from Dyer. This route is about 15.2 miles (24.5 km) and offers a straightforward, enjoyable experience on the Pennsy Greenway, ideal for a quick outing.


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