A note on these rides: You’ll want a good map. The Chicagoland Bike Map is available for $10 at most local bike shops; the City of Chicago’s bike map is free and good but doesn’t cover the suburbs. Distances are approximate because everyone’s starting and ending points will be different. For beginners, the ride north is better because you can take either the Metra or CTA back.
Three Floyds Brewpub and Flossmoor Station
Approximately 40 miles starting from Buckingham Fountain and ending at Ogilvie
→ Start: Get yourself to the Lakefront Trail. Bike south on the trail until you get to the end, at the Jackson Park Golf Course, and then take South Shore Drive (it has a bike lane) to the end. This is probably a good time to consult your map, because you’re going to zigzag a little bit as you head south to South Chicago Avenue. Take a left there and just after the road turns into 95th, you’ll see Calumet Fisheries on your right.
→ Calumet Fisheries (3259 E. 95th): Enough has been written about the wonders of this unassuming seafood shack that I shouldn’t have to convince you that you’re going to want fried fish for breakfast (or smoked fish—or fried shrimp, oysters, or frog legs). There’s no seating inside, but if you head toward the river you can sit on the bank and enjoy your meal in an industrial wonderland.
→ Eggers Grove Forest Preserve: Continuing along 95th Street, you’ll take a turn around Calumet Park, exiting on 100th and passing under the Chicago Skyway to pick up the Burnham Greenway, a rails-to-trails conversion that takes you through residential backyards and under crackling power lines before depositing you next to the forest preserve. It’s a scenic place for a rest next to Wolf Lake—and a former Nike missile site.
→ Three Floyds Brewpub (9750 Indiana Pkwy., Munster, Indiana): This is the trickiest part of the ride to navigate; getting to the brewpub on bike-friendly streets requires quite a bit of twisting and turning, and having a good map is key. From the forest preserve I usually take neighborhood streets south to 134th Street and follow that east across the Indiana state line, where I turn right on Sheffield Avenue. After that it’s pretty difficult to describe what to do, but the Chainlink has some good routes—or you can always use Google Maps. Calumet Avenue takes you to the industrial park where the brewery is located, but it’s so busy that I avoid it for all but the last mile or so (and for most of that mile, there’s a bike path that runs parallel to the road). Once you get there, you know what to do: Eat. Drink. Be merry. But not too merry, or you won’t want to get back on your bike afterward. Anyway, your next beer is only an hour away.
→ Flossmoor Station (1035 Sterling, Flossmoor): About ten miles west of Three Floyds, Flossmoor Station is an easy and relatively direct bike ride, mostly along Glenwood Lansing Road. The brewpub isn’t as hip or famous as its neighbor, but the beer is good, there’s rarely a wait for a table, and it’s so close to the Flossmoor Metra station that if you time things right you can catch a train back to the city ten minutes after finishing your drink (and bring along a bomber for the ride if you’re so inclined).
Lake Bluff Brewing Company
Approximately 20-50 miles from Evanston, depending on whether you take the Metra back (35-75 miles round-trip from downtown)
→ Start: The Edzo’s in Evanston (1571 Sherman). It opens at 10:30 AM, which is an excellent time for a burger and fries. If you live close to downtown you’ve already ridden a good ten miles to get here; if you’re a north-sider you’re still going to need some energy for the ride ahead. Get the char burger, which isn’t available at the new Lincoln Park location.
→ Baha’i House of Worship (100 Linden, Wilmette): A couple miles north of Evanston along Sheridan Road, this intricately carved nine-sided building is one of just seven Baha’i temples in the world. It was built in the first half of the 20th century amid various bizarre rumors: that it was a rocket ship, housed a white whale, was a fueling station for captured German submarines. The temple and surrounding gardens are open to the public daily.
→ Maria’s Bakery (410 Sheridan Rd., Highwood): Continue along Sheridan Road—you could also take the Green Bay Trail, but the mansions on Sheridan are pretty spectacular and the road is easy to bike on. Maria’s is a small Italian bakery with a friendly staff and excellent cookies (judging from the Yelp reviews all the food is good, but you may still be too full of burgers to try anything else).
→ Fort Sheridan: Just north of Highwood is Fort Sheridan, a former U.S. Army post that’s now a residential community, its buildings converted to condos and townhomes. On the outside, though, the pale-yellow brick—made with clay from the nearby bluffs—looks much like it must have 50 years ago, making it easy to imagine you’ve stepped back in time. The most striking landmark is the water tower, though it’s not what it used to be: because of structural instabilities, in 1940 it was shortened by about 60 feet (it’s now 167 feet tall).
→ Lake Bluff Brewing Company (16 E. Scranton, Lake Bluff): From Fort Sheridan, take the Robert McClory Trail right up to Lake Bluff, about a five-mile ride along the shady path. Stop at the brewpub for a Honey Badger golden ale or Skull and Bones double pale ale; from there you can either catch the Metra back to Chicago or take the North Shore Bike Path west to the Skokie Valley Bikeway and head south all the way to where it ends at Lake Cook Road. I’d recommend the latter, since the bike trail is probably the nicest of the ride, smooth and nearly empty, protected by trees from the highway nearby. If it’s not too late in the day you can stop at the Botanic Garden and take the North Branch Trail through the woods down to Edgebrook (to get back to Evanston, take Church Street east from the trail). The trail ends near another Metra line, but if you’ve still got some energy you can follow Elston’s bike lane back into the city. By now you may have worked up an appetite again; Superdawg (6363 N. Milwaukee) is right near the south end of the North Branch Trail.