Looking for the best trails around Darien?

Explore the best rated trails in Darien, WI, whether you're looking for an easy walking trail or a bike trail like the Four Sisters Bike Path and Peace Trail . With more than 120 trails covering 1199 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

Millennium Trail (IL)

Review of Northern Section

June, 2026 by tandemlovers

We rode the entire northern section this spring. 10 miles one way. Best place to park if you want to start in Round Lake Beach is the Round Lake Beach Elementary School parking lot. It's about a block and a half off the trail near the west terminus.
Most of the trail is well manicured fine limestone. Very good condition throughout. Scenery is excellent.
The signage is ok. Some intersections are well marked and others not marked at all.
There are several spur loops and many neighborhood access spurs. Use a map, these can get very confusing.
It loses a star for the signage and some rather intimidating grade crossings near the west end.

White River State Trail

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

May, 2026 by fredklausegger

Between Spring Valley road trailhead and Lyon the trail was closed due to 2 bridges being washed out

Muskego Recreation Trail

Beautiful trail with varying gravel conditions

May, 2026 by nkanute

great gravel cycling! Everyone complaining must be riding some skinny tires or should stick to the oak leaf- this was a very fun ride (I run 40mm semi slick tires and had no issues)

Accordion

Moraine Hills State Park Trail

My wife and I just purchased two e-Bikes and decided to use this place for our maiden voyage. This was also our first time at this state park. We really enjoyed the tails and the nature. We will be returning with cameras and fishing poles.

May, 2026 by garyboutte

My wife and I just purchased two e-Bikes and decided to use this place for our maiden voyage. This was also our first time at this state park. We really enjoyed the tails and the nature. We will be returning with cameras and fishing poles.

Kenosha County Bike Trail

Lots of shade and well maintained

April, 2026 by gypsycyn

A short but pleasant ride, with lots of shade, smaller wildlife, rest benches, even a couple pet stops with water dishes for the fur babies.

H.U.M. Trail

My honey had not.rode a bike in many years and didn't want to ride around a lot of people. So when we found this trail it became a favorite, very few people, flat, nice flowers and views. The parking is really easy at both ends.

April, 2026 by dambrisco

My honey had not.rode a bike in many years and didn't want to ride around a lot of people. So when we found this trail it became a favorite, very few people, flat, nice flowers and views. The parking is really easy at both ends.

Muskego Recreation Trail

If you continue on this trail west of 164 you will reach the Fox River and there is no bridge

March, 2026 by fredklausegger

If you continue on this trail west of 164 you will reach the Fox River and there is no bridge

Poplar Creek Trail

You need to cross several major roads, but the ride is beautiful!

March, 2026 by judy.meigel

You need to cross several major roads, but the ride is beautiful!

Cheese Country Recreation Trail

Beautiful multi-use trail. It is the only trail open to ATV/UTV’s in Southern WI

March, 2026 by dougmayer11

Beautiful multi-use trail. It is the only trail open to ATV/UTV’s in Southern WI

Prairie Trail (IL)

2026 ride in early March very rough

March, 2026 by w5q7jv7kc9

The trail from rusty nail north to Richmond was very rough and I lost the screws to my kick stand with all the bumps in the trail is there any plans to help smooth them out — I understand the horses share the trail but if they could help by staying to one side so us bikers have a chance on using the trail with out so many bumps dug into the paths¿

Great Western Trail (DeKalb, Kane)

jaro1311

November, 2025 by roachjames771

This trail starts behind my home in sycamore. I’ve ridden it dozens of times. I like to stop at the winners circle at the speedway and grab lunch. Flat and well maintained.

DeKalb Nature Trail

DeKalb Nature Trail

October, 2025 by idailey

This is a short path off the north end of the Kishwaukee-Kiwanis Trail. It was freshly repaved for a smooth ride with nice greenery on each side and a bridge over the river near the northwest end. The path is handicapped accessible and there was no traffic on the neighborhood cross streets. I didn't linger, but based on the number of squirrels crossing the path, I could imagine seeing a fair amount of wildlife at the right time of day.

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