Takuma Habu

• A full lap of the Lakeshore Front Trail – can get busy (and dangerous!) north of downtown.
• Try the Lollypop segment—lovely tarmac there!
• You can get to the Montrose Harbor Beach Beacon by going on the path to the south of W Montrose Harbor Dr (route).
• The best view of the city from the south is just by the Adler Planetarium (here).
  You can go around the Northerly Island Park from Adler Planetarium (route)!
• The best view of the city from the north is here.

Evanston (CW, CCW)
(68km/42miles)

• CW: North through downtown and coming back via the Lakeshore Front (avoiding the busy northern part).
• CCW: All the way up Lakeshore Front first and coming back through downtown (better for early morning rides when fewer people are on the Lakeshore Front).
• Argentinian ice cream @ FRIO Gelato. Try the “SAMBAYÓN” flavour.
• Newport Coffee is a good spot for coffee.

Glencoe
(95km/59miles)

• Sheridan Rd after Evanston is a great road to cycle (and you’ll see lots of cyclists).
• Don’t forget to take a photo of Baha’i.
• The route ends at Hometown Cafe in Glencoe.
• Slightly off route but another great ice cream place: Graeter’s in Hubbard Woods.
• If you’ve time, visit the Chicago Botanic Garden. Bike racks at the entrance.

Skokie Lagoons
(108km/67miles)

• This is a long way to get to somewhere close to Glencoe using the North Trail. Here’s a shorter version.
• See the stops mentioned above.

Highland Park
109km/68miles

• Ends at Once Upon a Bagel for some great… Bagels!
• Alternatively, a nice cafe is ArrivaDolce if Bagel isn’t your thing or you prefer coffee.
• This route avoids the northern part of Lakeshore Front (but of course you can take that back!).

Calumet Park
(32km/20miles)

• Circle around the park for interval training.
• Don’t forget to check out the pristine tarmac just south of Calumet Park.

Big Marsh
(48km/30miles)

• Fast route.
• Can smell a bit on S. Stony Island Av due to the landfill nearby but totally worth it!

Wolf Lake
(56km/35miles)

• State Line Road runs right over the IL/IN state border!
• Stop off at Grindhouse Cofee in Whiting.
• If you get stuck at the rail crossing by the Mascot Museum (I want to visit this!), use this route.
• If you like a (short, punchy) climb, check out the Casino climb.

Wicker Park (Indiana)
(80km/50miles)

• If you get stuck at the rail crossing just south of Calumet River, you can always use the over-bridge.
• If need to stop half way, there’s 18th Street Brewery. Has nice outdoor seating!
• The route turns loops back at Sip Coffee House, a great lunch/coffee stop.
• If you want (self-pour) beers instead, go check out Brewfest (a couple of blocks north of Kennedy Av from Sip Coffee).The owner (Evan) is amazing!
• Munster Donut (turn off South onto Calumet Av) has amazing donuts.

• You can find the other Grindhouse Cafe in Griffith. Two breweries: Wildrose and New Oberpfalz. Griffith town holds market/events.

Crown Point
(115km/72miles)

• Once you’re in Crown Point, you can find the other Sip Coffee House.
• You can also get amazing Latino food at Provincho.

Chicago Heights
(106km/66miles)

• Not really any food stops until you’re into Wolf Lake area so take some food!
• Here’s a nice loop around Sauk Trail.

• Check out the funky Librarium Cafe—a combination coffee shop/bakery and game store.
• Grab some beers and lunch at Cafe 339.
• You can also rest at Lakefront Park.

• The route takes you past the dunes to Beverly Shores, which is a beautiful road along the lake.
• Petrol station at Town Pines to get supplies (and it has a water tap you can use to fill up your water bottle).
• I heard you can grab nice(r) food at Chesterton but I’ve not tried anything myself.
• Here’s a shorter route (149km/93miles) that goes via Gary and main roads—I suggest only in groups and on holidays when there’s less traffic on the road.

• I don’t know of a good place stop so make sure take enough food.
• Can definitely have a picnic in Rubio Woods!
• If you want longer, try going down south to Old Plank Trail (131km/81miles).

Willow Springs
(60km/37miles)

• This is the shortest/quickest way of getting to Willow Springs from Hyde Park.
• Stop at Ashbary Coffe House (be sure to check the opening times if you’re riding in the morning) or at Imperial Oak Brewry.
• The fun actually begins from Willow Springs—see the routes below.

Willow Springs extensions

• Lots of climbs (for Chicago standards). The routes are set up for climbing but reversing makes it a little easier.
• Around Willow Springs: 20km/12miles.
• Palisades: 20km/12miles.
• Waterfall Glen & Black Patridge Woods: 54km/36miles.

• Takes Major Taylor trail and Cal Sag trail to get to Willow Springs.
• The route around Blue Island isn’t on Google/Garmin maps yet but don’t worry, the road exists!
• The bit after Blue Island (131st) is a little bumpy with lots of holes on the road…

Tour of the South Side Trails
(186km/116miles)

• Hits: Lake Front -> Erie Lackawanna -> Old Plank -> Centennial -> Cal Sag -> Major Taylor Trails.
• Frankfort on Old Plank Trail has Grounded Coffee that’s really nice!