Looking for the best trails around Hartford?

Explore the best rated trails in Hartford, WI. Whether you're looking for an easy walking trail or a bike trail like the Peebles Trail and Brooke Street Trail. With more than 53 trails covering 649 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

Wiouwash State Trail

Meh..

October, 2022 by the_masseuse

Did the whole Southern segment. Was a decent trail..the usual trail trail..nothing spectacular. The part of the trail running along the water is pretty. Low rating is for the all the horse **** up n down the entire trail. The leaves this time of year really hide the piles.

Lake to Lake Bike Trail (WI)

A very well maintained Trail with services and many parking lots. We experienced a lot of foot and bike traffic especially as we got close to the campgrounds.

October, 2022 by hardenmedia

A very well maintained Trail with services and many parking lots. We experienced a lot of foot and bike traffic especially as we got close to the campgrounds.

Glacial Drumlin State Trail

East to West starting in Glendale and ending in Madison

October, 2022 by martinaxe

I started out my ride from my home about 9 miles north of downtown Milwaukee where I caught "the Hank" and made my way west to the Glacial Drumlin Trail. I started out at 3:00 am, so it didn't really get light out until I got to about Wales. After that, I was on non-paved trail (my personal fav) for the rest of the ride to Madison. The trail is really very nice and mostly flat with a lot of varying landscapes. Since it's October, there were a ton of migrating birds and pretty good fall colors all along the trail, and I didn't see another human riding until I was about 5 hours into my trip near Lake Mills. The only thing keeping me from giving this trail 5 stars are the bridges, which are mostly bad. They do have a rubber strip running down the middle of them which helps, but they are still mostly bouncy and you have to deal with a 3-6" rise at the start of each of them. The west end of the trail was closed near Cottage Grove, and I had to take a detour on streets, which was fine. This is a highly recommended ride, especially during fall.

Accordion

Old Plank Road Trail (WI)

Nice trail but meh

October, 2022 by mylovelyparasite_tl

I started in Greenbush and went to Sheboygan. It came out to 17.2 miles, one way. Overall the surface is smooth with only a few places that were just a little rough. Lots of hills, which are normally great, because no matter how much it hurts going up, you can always coast down. Except that at the bottom of most of the hills, you have to stop at a road crossing. The views of the Kettle Moraine Forest from the hilltops were nice as the Fall colors are starting to come in. Yes, being right next to Hwy 23 was noisy and smelly from the exhaust. Overall though, I enjoyed the ride. Plenty of spots to stop and rest. A river. Wide open farmland. I guess this trail could suck or be fantastic, depending on one's expectations and perspective.

Oak Leaf Trail

Extension to Bender Park Open but not yet ready for Use

September, 2022 by buehler868

The Milwaukee County Parks, Oak Leaf Trail webpage says the extension of the South Shore Line segment is open to Bender Park. It is not yet show on the TrailLink map. On my September 2022 trip up to the Oak Leaf Trail, to do the original South Shore Line and the Oak Creek Line, I decided to see what the new extension was like. Yes, it is open with routing signs in place and a creek bridge constructed. But the surface is made up of 1-inch sized crushed stone which is typically used as a base layer under asphalt pavement. Even though I have a gravel bike, from Drexel Ave I only made it down to Pennsylvania Ave and gave up the going further. It’s just too rough. I made the trip back using highways. I searched on the internet, and it seems that the funding grants describe a 2023 completion. I hope what is the case is the asphalt paving will be done in 2023.

Oak Leaf Trail

Riding the Southeast Quadrant

September, 2022 by buehler868

On my third trip up to the Oak Leaf Trail I did what I call the Southeast Quadrant. I parked at Greenlawn Park and did the trail and spurs down to the Racine County line and up to Cupertino Park near the Lake Michigan Ferry. What I liked about this trip was the variety in the trail. Segments consisted of rails to trails (with powerlines), trail in parks, separate trails on arterial streets, the parkway roads, and rural highways. The long, southerly segment in the forest on the bluffs along Lake Michigan was the prettiest segment of my three trips on the Oak Leaf Trail. The north segment along Lake Michigan was closer to the water and gave a nice view of downtown Milwaukee.
One concern is the trail is being extended to Bender Park, which is popular but what about funding of maintenance of the trail that already exists? This section had some of the asphalt showing its age with the periodic shrinkage cracks giving that frequent bothersome bump. One hidden path bridge at the bottom of a hill had plywood covering over rotted deck boards, which at speed was very rough. But none of these maintenance issues should stop any one from coming to use the Oak Leaf Trail. I do recommend stopping at the coffee/ice cream store the trail parkway passes at Chicago Ave.
I am sure the rail to trail segment from Greenlawn Park was the former North Shore Interurban Line (to Chicago) that my folks took on their honeymoon to Milwaukee in 1944.

Ozaukee Interurban Trail (Route of the Badger)

Great trail; all paved. Lots of things to do along the way; many different stopping places available!

September, 2022 by jmglz

Great trail; all paved. Lots of things to do along the way; many different stopping places available!

Eisenbahn State Trail (Route of the Badger)

Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!

September, 2022 by jmglz

Love this trail! Can find several restaurants to eat at, play miniature golf, get a great cup of coffee all on the trail! Great trail!

Lake to Lake Bike Trail (WI)

Love this trail! Beautiful ride; worth the trip to ride.

September, 2022 by jmglz

Love this trail! Beautiful ride; worth the trip to ride.

Old Plank Road Trail (WI)

Extends beyond the old wade house now. Started there and ended in Sheboygan. First long ride on the new eBikes. 360 mapped it and loaded to street view.

September, 2022 by hardenmedia

Extends beyond the old wade house now. Started there and ended in Sheboygan. First long ride on the new eBikes. 360 mapped it and loaded to street view.

Lake Michigan Pathway

A very pleasant ride

September, 2022 by yospiff1

I started from a local community center near the south end, (asking permission to park my car there first). Also gave them a small donation when I returned. Most of this trail hugs the coastline, though the last few miles is along city streets. At the northwestern end of the trail, I found it joined up with a local rail trail, which runs from 3 Mile Road to Layard Ave. paralleling Douglas Ave., though it is not on Traillink. So I took that a few miles south and rode some city streets until I rejoined the Lake Michigan Pathway. In several places, the trail is not obvious or well marked, so keep your traillink app open to see where you are if you aren't sure. I recall one spot that looked like an alley past an industrial area, but it went down to the marina and the trail. Once past that, there are signs periodically to point you the right way.

Oak Leaf Trail

Riding the Northeast Quadrant

September, 2022 by buehler868

Starting at the Brown Deer Village Park and heading south, I did what I call the NE Quadrant of the Oak Leaf Trail, consisting of the trail north of downtown Milwaukee. If you look at the trail map, there are some loop segments and some spurs that can be done. I did them all. Some segments are on old railroad beds and some on subdivision roads or separated bike lanes. Some sections were newly paved. You head back north after reaching downtown Milwaukee, but I stopped for lunch at the brat/beer garden along the trail at the art museum. Especially useful is having the downloaded TrailLink map as the connection to the parts of the Oak Leaf Trail south of downtown are not that well marked at the ongoing highway construction. There were good trail signs at other periodic locations.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Your account has been deleted.