The Lakefront Trail is a highlight of Chicago’s cycling network, but some miles are certainly better than others.

Every spring, as Chicagoans pull their bikes out of the garage, the Lakefront Trail is filled with cyclists, pedestrians & beach-goers alike. If you’re visiting for a couple days, it may be hard to know which parts of this must-visit trail are actually worth visiting, and which should be skipped. Below, I’ve reviewed each of the ten segments (as divided by the Chicago Park District)so that you can plot out your bike trip better.

1: Ardmore to Montrose

The north trailhead is tucked away from traffic and the roads by there are mostly quiet which makes navigating onto the trail at this point fairly easy. If you love the beach, Montrose Beach is hard to beat in Chicago since it has plenty of space to spread out and doesn’t too crowded, even in the height of summer. However, this also means that there’s lots of families here with small children who are NOT paying attention to cyclists, which is an unfortunate trend that continues throughout the whole trail, so get used to slowing down and being alert when there’s a beach nearby (although it’s always good practice to be alert).

2: Montrose to Fullerton

This section goes along the Sydney R. Marovitz Public Golf Course as well as the Belmont & Diversey Harbor, which are very scenic. If you’re looking for a mid-ride snack, Two Wheel Tacos is definitely worth checking out. As far as north side segments of the trail go, this one remains relatively quiet, which makes it a favorite for myself.

3: Fullerton to North

North Avenue Beach is one of Chicago’s busiest beaches during our beautiful summer months, but the trail separates and runs closer to the iconic Lake Shore Drive than the busy beaches. This means that this segment is not overrun by clueless beach-goers at the expense of not having as nice scenery – unless you like looking at the nearby traffic.

4: North to Oak

While Oak Street Beach is smaller and not quite as busy as North Avenue Beach, there is not much separation between the walking and cycling paths here. This means that all the clueless pedestrians that were avoided one section to the north, are now funneled right onto the same trail. Be VERY alert here. I love that folks from all over the place come to visit our beautiful lakefront, but it does mean that cyclists need to be very careful of people who do not necessarily know to look out for bikes.

5: Oak to Ohio

While this section doesn’t get as crowded as the stretch a couple miles north, there are some other factors that make this segment quite difficult to traverse. First, the trail has a sideways slope to it that can make it difficult to pedal in a straight line. Second, when the waves are even a little bit choppy, the water can splash onto the path making it quite slippery. If you’re interested in any open water swimming at all, this is the best place to do it in my opinion – Ohio Beach is always filled with triathletes training for their swim leg as soon as the water gets warm enough.

6: Chicago River to Roosevelt Rd.

Once you pass over the Chicago River and start going along the loop, things start to get mostly quiet and there are some fun attractions along this stretch. The Bean & The Art Institute of Chicago are not too far from the trail, and it runs right along Grant Park, Buckingham Fountain and Monroe Harbor. In terms of sights to see per mile, this segment certainly packs it all in.

7: Roosevelt to 35th St.

This is really where things really start to calming down. Personally, I feel like the south side of the Lakefront Trail is totally underutilized, which makes it a great way to get some fast & fun training miles in. In this segment, the trail hugs the outside of the Shedd Aquarium and skirts by the rest of the museum campus.

8: 35th to 41st St.

Burnham Park has one of the most picturesque shots of the Chicago Skyline from the southside. Not to mention the protected prairie grassland that the trail meanders through for a couple miles in this segment. The beautiful natural views here are some of the best along the trail and they’re made all the better for having our iconic skyline popping up behind all of it.

9: 41st to 55th St.

There’s not a whole lot of features along this stretch, which makes it nice & quiet for any cyclist looking to get some sprint intervals in without worrying about running into any wayward pedestrians. For those who like to keep things chill, this segment has some nice, serene views of Lake Michigan and the surrounding wildlife. Promontory Point is also an ideal spot to stop for a mid-ride, lake-side picnic – there’s lots of shady spots in the grass to rest comfortably for a little bit.

10: 55th to 71st.

As you reach the south trailhead of the Lakefront Trail, things get a little bit busier again as you pass by the Museum of Science & Industry, two different golf courses and more beaches. Chicago history enthusiasts might also be interested in checking out where the grounds of the 1893 World’s Fair stood by biking through Jackson park. South Shore Brew on Yates Boulevard is a great spot to stop for a post or pre-ride coffee.