There’s a reason that the Chicago Lakefront Trail makes an appearance in just about every movie or show set here: it’s a totally unique, instantly recognizable, defining feature of the city. Take a minute to think about it, as you’re riding north over the bridge at Diversey Harbor, the waves of Lake Michigan rising and falling just a few meters from your tires: this is the third largest metro area in the country, and boasts a continuous 20 miles of public lakefront, winding through expansive parks and beaches. While other Great Lakes cities were busy industrializing their shorelines at the turn of the century, urban engineer Daniel Burnham’s 1909 Plan of Chicago preserved almost the entirety of Chicago’s lakefront for public use, echoing the public parks of European cities.
If you need something else to chew on, let’s get brunch! Exit the Lakefront Trail at Lawrence Avenue, hanging a right on Sheridan Road to pedal up to Tweet, one of the coziest spots on the city’s north side for great, vegetarian-friendly comfort food, with local artists’ work covering the walls. Tweet’s Bloody Mary is consistently voted one of the best in the city, and if you’re wondering—yes, you’ve earned it.
Take nearby Winona Street west through a few peaceful apartment-lined blocks to Clark Street, and you’ll find yourself in the heart of Andersonville; a bustling, historically Swedish neighborhood now home to loads of independent shops, bookstores, and cafes. In Andersonville, we recommend George’s Ice Cream & Sweets, Women & Children First bookstore, the Swedish American Museum, Kopi Travelers Cafe and, of course, a bike shop: Johnny Sprocket’s.
Continue west to Ravenswood Avenue, an almost car-free street nested between the grassy slope of Metra regional rail tracks and industrial lofts. Heading south to Wilson Street, make a right toward Lincoln Square. Take your time on this stretch—there are some really beautiful single-family homes and gardens between Damen Avenue and Lincoln Avenue, and cars generally avoid this side street.
Once you hit Lincoln Avenue, you might want to find a spot to lock up your ride for a while—there’s a lot to do in Lincoln Square! Peruse the lovingly curated record collection at Laurie’s Planet of Sound, have an amazing Indian meal at Essence of India, strum a guitar or banjo at The Different Strummer music store at the Old Town School of Folk Music, or sample some authentic European food and beer at Gene’s Delicatessen or Huettenbar. Sound overwhelming? Chill out and catch a flick at the recently renovated Davis Theater, a hundred-year-old moviehouse at the center of the neighborhood. Even late into the night, the streets of Lincoln Square are buzzing and well lit, so your ride home is sure to be safe, and entertaining!
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Housed in a small art-deco building just off the Lakefront Trail in Uptown, Tweet's cozy atmosphere is perfect for getting some writing done on a rainy morning, or sharing one of their award-winning...
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Built in 1918, the Davis Theater is probably best known as a weathered and loved community movie theater in Lincoln Square. Recently renovated after a year of construction, the Davis has embraced its...
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Since 1957, the Old Town School of Folk Music has brought some of the most vital and influential performers through Chicago, as well as offering private and group classes.
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Consistently one of the best-curated and most progressive bookstores in Chicago, hosting readings, book groups, and kids' storytime.
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A mainstay of the Chicago cycling scene, Johnny Sprockets has a few locations throughout the city's north side, all offering personable, professional sales and service.
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A proudly employee-owned shop in West Town, Comrade Cycles stocks some of the best commuter gear in town, and is ready to tackle any kind of project, from brake pad replacements to tuning your ride...
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Heritage General Store, on north Lincoln Ave., offers a bright, quiet place to get some work done over a cup of coffee, while checking-out some beautiful handbuilt frames.
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One of Chicago's oldest and best-known bike shops, Village Cycle Center consistently provides solid bike-fitting services, and can have a new bike ready to ride in less than an hour.
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This cozy storefront at the center of Logan Square is one of the few shops in Chicago that offers used bikes, as well as a great selection of commuter bikes and gear.
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Formerly the Hotel Burnham, this National Historic Landmark offers access to the Loop's nightlife and business centers, as well as quick access to the Lakefront Trail and Museum Campus.
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Offering complimentary bicycles and yoga mats to guests, this classy hotel is located in Chicago's bustling River North neighborhood.
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Luxury hotel with available bike rentals, overlooking Millennium Park and the Lakefront Trail
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Beautiful, refined bed & breakfast in Chicago's historic Old Town neighborhood, with easy access to downtown and the city's north side.
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This bed & breakfast nestled in the heart of Chicago's Wicker Park, offers affordable and comfortable rooms in one of Chicago's most vibrant neighborhoods.
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Note: Erosion caused by surging waves off Lake Michigan has caused the trail to collapse in sections. The eastern half of the trail along Lake...
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The northern section of the Tinley Creek Trail is a series of color-coded connected loops and spurs that weave through several forest preserves in...
Overview The Cal-Sag Trail (also known as the Calumet-Sag Trail) runs for 16.2 miles and connects several communities and additional trails, as...
Overview The Chicago Lakefront Trail is aptly named; it spans 19 miles along the shore of Lake Michigan, going right through downtown Chicago to...
Overview The North Branch Trail follows the North Branch of the Chicago River for 25.5 miles through Cook County. The trail was originally a dirt...
Overview The Illinois Prairie Path (IPP) was one of the nation’s first rail-trail conversions. The 58-mile trail consists of five connected trail...
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Overview The Bloomingdale Trail, part of “The 606” park system, is a 3-mile, elevated rail trail on Chicago’s northwest side. Built on a former...
Overview The Illinois and Michigan Canal State Trail follows the eponymous waterway alongside the Illinois River. It traverses the I&M Canal...
