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United States
Indiana
Lake County

Highland

The best cycling routes around Highland

4.9

(24)

112

riders

24

rides

Touring cycling around Highland features a network of accessible routes, primarily characterized by flat terrain and minimal elevation changes. The region offers a variety of trails suitable for relaxed rides, often following former railway lines or river paths. These routes provide smooth surfaces, making them ideal for touring cyclists seeking straightforward navigation and consistent gradients. The landscape is generally open, with some sections passing through developed areas or alongside waterways.

Best touring cycling routes around Highland

  • The most popular touring…

Last updated: August 18, 2026

5

riders

#1.

Monon Trail loop

54.1km

03:04

60m

60m

The Monon Trail loop offers a diverse touring cycling experience, taking you through varied scenery from quiet farmlands to lively urban districts. This moderate 33.6-mile (54.1 km) route, with a…

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Moderate

This easy touring cycling loop offers a delightful blend of natural and urban scenery, perfect for a quick outing. You'll pedal along the paved Erie Lackawanna Trail, a former railroad…

Easy
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This easy 19.1-mile touring cycling loop combines the Pennsy Greenway and Erie Lackawanna Trail, offering diverse scenery and gentle terrain

Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Highland

Hiking around Highland

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Running Trails around Highland

Tips from the Community

maniboyflex
June 30, 2025, Chase Street Conservation Area

This quiet nature reserve in Indiana features dirt and gravel paths surrounded by wetlands and trees. Be prepared for uneven surfaces and a few puddles after rain. It's a gem for those who like cycling surrounded by forest.

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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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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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The Monon Trail is a 4.4-mile rails-to-trails path that follows the route of the former Monon Railroad. This section connects the suburbs of Hammond and Munster. This trail is not to be confused with the trail of the same name in Indianapolis.

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This pedestrian bridge sits above the intersection of Calumet Avenue and River Drive and helps increase safety at the busy intersection off I-94.

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The Erie Lackawanna Trail is an almost 18-mile rails-to-trails path that runs along the former Erie Lackawanna Railway.

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The Little Calumet River starts in Gary and flows northwest. With significant stretches in both Indiana and Illinois, the Little Calumet River is known for linking cities and towns throughout the Chicago region.

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Frequently Asked Questions

What kind of terrain can I expect on touring cycling routes in Highland?

The touring cycling routes in Highland are primarily characterized by flat terrain and minimal elevation changes. You'll find smooth surfaces, often following former railway lines or river paths, making them ideal for relaxed rides. The region features extensive greenway networks, providing straightforward navigation and consistent gradients.

Are there many easy or beginner-friendly touring cycling routes in Highland?

Yes, Highland is well-suited for easy and beginner-friendly touring cycling. Out of the 17 available routes, 11 are classified as easy, focusing on flat paved paths and accessible greenways. These routes are perfect for those seeking a relaxed cycling experience.

What are some popular routes for touring cyclists in Highland?

Local touring cyclists frequently enjoy the Monon Trail loop, a moderate 33.6-mile route with gentle undulations. Another favorite is the Pennsy Greenway and Erie Lackawanna Trail Loop, an easy 19.1-mile path offering a smooth ride through varied scenery.

How long do touring cycling routes in Highland typically take to complete?

The duration varies by route and your pace. For example, the Monon Trail loop, which is 33.6 miles, typically takes about 3 hours and 4 minutes. Shorter routes like the Erie Lackawanna and Little Calumet River Trail Loop (5.3 miles) can be completed in around 30 minutes.

Are there any family-friendly touring cycling options in Highland?

Absolutely. The region's extensive greenway networks, flat paved paths, and minimal elevation changes make it ideal for family cycling. Many routes are classified as easy, providing a safe and enjoyable experience for all ages. The Maynard Lake – Pennsy Greenway loop from Munster is a great option, leading through suburban areas and alongside natural features.

What can I see along the touring cycling routes in Highland?

Many routes pass through or near natural features and developed areas. You can explore highlights such as the Erie-Lackawanna Rail-Trail, the Oak Savannah Trail, and the Illinois Pennsy Greenway. The Chase Street Conservation Area also offers a chance to experience local nature.

Are most touring cycling routes in Highland circular or point-to-point?

Most of the touring cycling routes in Highland are designed as loops, offering convenient circular journeys. This allows you to start and end your ride at the same location without needing to arrange transport back. Examples include the Monon Trail loop and the Pennsy Greenway – Pennsy Greenway loop from Dyer.

What do other touring cyclists enjoy most about cycling in Highland?

The area is highly rated by the komoot community, with an average score of 4.8 stars from over 11 reviews. Reviewers often praise the well-maintained paths, the flat and accessible terrain, and the variety of greenway networks that make for enjoyable and relaxed rides.

When is the best time of year to go touring cycling in Highland?

Given the flat terrain and greenway focus, spring, summer, and autumn generally offer the most pleasant conditions for touring cycling in Highland. These seasons provide comfortable temperatures and less chance of icy conditions, ensuring a smooth ride. Always check local weather forecasts before heading out.

Are there any cafes or amenities along the touring cycling routes?

Many routes in Highland pass through or are close to suburban areas, which means you'll often find opportunities for cafes, restaurants, and other amenities nearby. While specific facilities vary by route, the urban and suburban integration of the greenways generally provides convenient access to services.

Are there options for longer, multi-day touring cycling trips in Highland?

While individual routes in Highland are typically shorter, ranging from 5 to 33 miles, the extensive network of interconnected greenways and trails offers the potential to link multiple routes for a longer, multi-day touring experience. You can combine paths like the Pennsy Greenway and Erie Lackawanna Trail to extend your journey.

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