Route Options • Route
Description • Century
Our route parallels Lake Michigan through Chicago
and the north shore Chicago suburbs and is almost
entirely flat, following fully paved and signed bike
paths and trails about 75% of the way. When it does
not follow paths, the route primarily follows low traveled
residential and secondary roads.
Participants from the Chicago area will be able to
get a great day of cycling close to home!
Here for more information about
the types of roads and bike paths the route will
Here for more information about our
riding policies and procedures.
There are four possible route options that
you can ride.
Hammond to Kenosha
This route is the basis for the event. You will
start your ride right over the Illinois/Indiana border in Hammond
and finish your ride in Kenosha, riding through 3 states
in one day.
Hammond to Kenosha Century
In order to complete a century, you will ride a loop out
of the ending location in Kenosha to add on enough miles
in order to ride over 100 miles. It will not matter which specific
route segments or options you ride from Hammond to Kenosha
in order to complete the century.
Hammond to Waukegan
For this route, you will start the ride in Hammond
but end in Waukegan, IL.
After you arrive in Waukegan
you can then take the Metra train back with your bike to Chicago
or any Metra station in between. This ride is perfect for riders
who do not want to ride the full
from Hammond to
Kenosha or for riders who want to depart the ride early.
Here for more information about taking the Metra train
Hammond to Waukegan Century
If you want to complete a century ride but do not want
to wait at the end in Kenosha for our return transportation
service, this route is the one for you! After you arrive at
the end in Kenosha, you will turn around and ride the route
back to rest stop 4 in Waukegan.
From Hammond to Rest Stop 1 in Downtown Chicago
The event will start at Wolf Lake Memorial
Park in Hammond. The park is in Indiana on
shore of Wolf Lake, which the
border passes directly
The route begins by following a brand new bike path on the
shores of Wolf Lake immediately out of the starting location
and part of the path includes a brand new bridge over Wolf
From there, you will ride directly along the Illinois/Indiana
state line for about 3/4 of a mile to the Indiana state sign
- make sure to stop and get a picture!
After you head west from the Illinois/Indiana state line
you will enter the city of Chicago and ride along the Burnham
Greenway Trail which is a rails to trails bike path that
up through quite a bit of Chicago's south side. From there
you will ride through Calumet Park and onto the bike path
along the brand new "New
Lake Shore Drive" which
goes through 600 acres that are currently being redeveloped
that once housed
U.S. Steel's South Works plant. You will then continue to bike
through Chicago's south side passing by
At 71st Street, Chicago's world famous
Lakefront Path begins and you will bike on the Lakefront
One of the most amazing things you will ever see is when
you catch your first view of the Chicago's awe inspiring
skyscrapers and beautiful lakefront as you're coming up the
Rest Stop 1 in Downtown Chicago to Rest Stop 2 in Skokie
Our first rest stop will be at DuSable Harbor
in downtown Chicago located directly off the Lakefront
Bike Path. Located in the heart of downtown at the foot of
Randolph Street, the harbor is surrounded by Chicago's
end of the lakefront path we will travel along very low
traveled residential streets through Chicago's north side,
riding past many of Chicago's famous "bungalow" style
houses. Then you will then bike to
our next rest stop in Skokie on the North Shore Channel
Trail, which follows the North Shore Channel canal. Running
almost the entire length
Northshore Sculpture Park which contains over sixty
large scale contemporary sculptures on exhibit.
Rest Stop 2 in Skokie to Rest Stop 3 in Lake Forest
From rest stop 2 in Skokie you will bike to the start of
the Green Bay Trail in Wilmette. The Green
Bay Trail parallels the current Metra North
Line and is directly on the track bed that once used
was for the Chicago
North Shore and Milwaukee Railroad, a train
running more than 50 years ago.
Make sure to keep
for the remnants of the concrete bases of the old stations,
especially in Winnetka and Glencoe!
From the Green Bay trail, you will bike to
the start of the Robert
which you will follow is almost
route to rest stop 3 in Lake Forest. Along the way
you will bike through the
famous Ravinia festival in Highland Park and directly
Sheridan in Highwood, a former major United States
Army post officially closed by the Army in 1993.
Metra Train Options into downtown Chicago
In case you are unable to finish the ride, you can easily
take a Metra Train back into downtown Chicago from rest
stops 3 and 4. Bicycles are allowed on the train, subject
Here for more information about Return
Metra Train Service.
Rest Stop 3 in Lake Forest to Rest
Stop 4 in Waukegan
Out of rest stop 3, you will continue following the Robert
immediately past the Great
Lakes Naval Station, home
of the United States Navy's only boot camp and the largest
training station in the Navy.
Rest stop 4 is directly at Waukegan Harbor. Going
into and coming out of rest stop 4 there are some very
steep hills so get
climbing them! Our rest stop
is in a perfect scenic location and we know the cool breeze
off the lake will feel great! In addition,
there is also an ice cream stand, hot dog stand, and deli
directly at the rest stop so make sure to bring some cash
and enjoy an ice cold ice cream cone on a hot summer day!
The Waukegan Metra station is only two blocks from
rest stop 4 and you can either choose to end your ride
there and take the Metra train back into Chicago or ride
Kenosha and back to rest stop 4 if you don't
want to take our return transportation service. Fully assembled
bicycles are allowed on the train, subject to restrictions.
Here for more information
about taking the Metra train from Waukegan.
Rest Stop 4 in Waukegan to the Ending Location in
About three miles
after rest stop 4, the Robert
McClory Trail continues with a crushed
surface through the remainder of Illinois. You will
have the option of either following this
path for over eight straight miles across
the state line into Wisconsin or continuing on a fully
paved on road option primarily following residential
At the Illinois/Wisconsin state line the path becomes
paved and all participants cyclists will
follow it again.
After you cross into Wisconsin the route will turn east
two miles then turn back north. Here you will be able
to ride directly along the shores of Lake Michigan as
the route makes its way to our ending location through
Our ending location in Kenosha will be near the heart
of downtown Kenosha at Eichelman Park right to Lake Michigan!
There is a beach is right at our ending location
into the lake to cool off and refresh
ride that day! Our ending location is also very close
to downtown Kenosha and there will be TONS of places
for you to get some food or drinks at local establishments
while you are waiting for our return transportation service
Both century options will begin at the ending location
in Kenosha. After you arrive at the ending location, you
can replenish yourself
departing to ride either
Kenosha Century Loop Option
If you want to get in a century ride and will
ultimately be departing from Kenosha, our century
be a counterclockwise
loop route that begins and
ends at the ending location. You will head
north for just over two miles directly along the Lake Michigan
shoreline, then head west and back south to the end of
the bike path from Illinois. From there you will head
east again and ride the same route you already
rode, back up directly along the Lake Michigan shore back
into the ending location. It's like getting a Lake Michigan
two for one
Kenosha to Waukegan Century Option
If you want to get in a century ride and will
be departing from Waukegan, you will turn around from the
ending location and ride the exact same route back to rest
stop 4 in order to catch the Metra train back from there.