Cannondale CAAD10 4 (2012)

Ever since I picked up a road bike from Craiglist in June 2019, I have come to love cycling. If I'm not working, then I'm usually cycling around...


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Favourite routes

Click on the destination name to get the relevant Garmin route that starts in Hyde Park. I've only included routes I've done myself. I'll keep adding more as I try new routes!

All routes are on Garmin Connect.


Last updated: 1 June 2021.

Destination Distance Tips
NORTH
Lakeshore Front 62km/39miles
  • 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).
  • Best view of the city from the south is just by the Adler Platarium (here).
  • You can go around the Northerly Island Park from Adler Platarium (route)!
  • 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 ream @ FRIO Gelato. Try the "SAMBAYƓN" flavour.
  • A few cafe stops in Evanston (e.g., Pete's 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.
  • 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 routes avoids the northern part of Lakeshore Front (but of course you can take that back!).
  • SOUTH
    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.
  • McCormick-South Chicago 41km/25miles
  • Great for early morning rides when there's usually little traffic on S MLK Dr. and S Chicago Av.
  • 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.
  • Combination routes
  • Big Marsh & Wolf Lake: 64km/40miles.
  • McCormick-South Chicago & Wolf Lake: 64km/40miles.
  • McCormick-South Chicago, Big Marsh & Wolf Lake: 82km/51miles.
  • 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.
  • Griffith 89km/55miles
  • 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, an amazing Donut shop with an old bank vault full of comic things (now CLOSED :(). 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.
  • EAST
    Hobart 115km/72miles
  • 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.
  • Indiana Dunes 195km/121miles
  • 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.
  • WEST
    Rubio Woods 91km/57miles
  • 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.
  • Cal Sag & Willow Springs 90km/56 miles
  • 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...
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