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 on my own or with UCVC/Hyde Park Cycling.

Find me on Strava.

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: May 2022.

Destination Distance Tips
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 cream @ 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!).
    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.
  • 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!
  • 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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