September 2016 Cycling Races, Rides & Events

North Shore Century 2013 Joy Sherrick Higher GearPhew! It’s hard to believe that summer is wrapping up, the kids are back in school and that, soon, the leaves will be changing and days will be getting shorter.

But no need to rush into hibernation! There is plenty of cycling to be enjoyed yet. September brings us some of our favorite local century rides. It’s also the perfect time to test the local triathlon waters (or to at least to go out and support our local triathletes).

Don’t hang your bike in your garage just yet! Check out these local cycling events for September and October…


2014 North Shore Century Evanston Bike Club Specialized Higher Gear


September 2016 Cycling Races, Rides & Events


11 September: Harmon Hundred
Wilmot, WI
2016 marks the 47th year of this annual, non-competitive scenic ride through southern Wisconsin. Choose from 25, 50, 75 or 100 mile routes. Enjoy well-marked and quiet country roads, cue sheets, SAG support, friendly volunteers and our well-stocked rest stops that receive RAVE reviews every year. Free showers will be available after the ride


11 September: Sub-5 Century
Hampshire, IL
The seventh annual Sub-5 Ride for Parkinson’s is a life-changing event for those who take pride in their personal accomplishment and create hope for those afflicted with Parkinson’s disease. If you’re a serious road cyclist there are two options for you to participate. The featured event, is a timed, 100-mile ride. Competitive cyclists are challenged to participate in teams to complete a 100 mile course in less than five hours. The course record of 3:55:57 for the full century was set by Mike Heagney in 2015. Can you beat that? For serious cyclists who enjoy riding in smaller groups or alone, there is also a timed Metric Century (62 miles).

Higher Gear customer Glenna Lampner tells us: “A century is a party. It’s a party and they’re feeding you.”


11 September: Ironman Wisconsin
Madison, WI
Aaron Sherrick 2015 Ironman IM Madison Wisconsin Wattie Ink Specialized Shiv EvadeIn the bucolic college town of Madison, triathletes compete for one of the qualifying slots for the 2017 IRONMAN World Championship in Kailua-Kona, HI. The one-loop swim takes place in Lake Monona in downtown Madison. Spectators will have a panoramic view of the swim from the Monona Terrace, designed by Frank Lloyd Wright. The bike course takes riders 16 miles out of town before beginning two 40-mile loops in rural Dane County. The course offers many tough climbs and turns throughout, but athletes will get a lift as they pass through the crowds at the Verona Loop Festival. Athletes will complete two run loops, which include downtown Madison, the University of Wisconsin campus, Camp Randal Stadium, State Street and the scenic path alongside Lake Mendota. Spectator support for Ironman Wisconsin is legendary across the Ironman race circuit.

Thinking about triathlon? Meet a Higher Gear customer who encourages you to “tri.” >>


16 – 18 September: Stop the Cycle 2016
Spring Grove, IL
Stop the Cycle of Abuse is a three day cycling tour and camping event. With our base camp located the beautiful Chain of Lakes State Park. The tour consists of three 60-mile loops through beautiful Lake, Kenosha and McHenry Counties. Options are available for 1, 2 or 3 days. This fully supported ride is not a race; it is an awareness and fundraising event.


NST North Shore Triathlon Wilmette Illinois 2016 Precision Multisport swim bike run18 September: North Shore Triathlon
Wilmette, IL

Back for its fourth year, the North Shore Triathlon once again brings triathlon close to home with stunning sprint-distance and supersprint-distance courses through the beautiful Wilmette, Winnetka and Kenilworth neighborhoods of the North Shore. If you’re looking for a local race that is fast, flat, and fun, you’ve found the race for you! There’s a relay option as well as volunteer opportunities.

HG customers, take advantage of $10 off with discount code!

Thinking about triathlon? Meet a Higher Gear customer who encourages you to “tri.”


18 September: North Shore Century
Evanston, IL
North Shore Century 2015 Evanston Bicycle Club Higher Gear Elyer SherrickThe North Shore Century offers incredibly scenic biking. You’ll experience luxurious neighborhoods, view unique architectural treasures, pedal down tranquil tree-lined streets and feel the refreshing breezes of Lake Michigan. Open it up in the flat to rolling countryside between Chicago and Wisconsin. The 100-mile ride is what this event is famous for. For those looking for a more leisurely day out on the bike with the opportunity to see some of the most architecturally impressive homes, choose from 70-, 62-, 50- or 25-mile rides.

Read Higher Gear’s own Joy Sherrick’s experience at the 2013 North Shore Century >>

Meet a young 2014 North Shore Century participant >>

A Gearhead used the 2016 NSC to say farewell to the north shore >>


25 September: Apple Cider Century
Three Oaks, MI
2016 marks the 43rd annual Apple Cider Century in Three Oaks, Michigan. This Century is a one-day 15, 25, 37, 50, 62, 75 or 100 mile bicycle tour of the orchards, forests and wine country in and around Three Oaks, Michigan. It hosts over 5,500 cyclists riding through the countryside and towns of Southwest Michigan. Casual to expert riders enjoy the food, sights and sounds and camaraderie of fall cycling.

Higher Gear customer Glenna Lampner tells us: “A century is a party. It’s a party and they’re feeding you.”


25 September: Prairie Pedal
Decatur, IL
Prairie Pedal is an annual bicycle ride fundraising event for the Macon County Conservation Foundation held in the fall. 20-, 40- and 62-mile routes are available. All proceeds support the conservation of natural areas and wildlife in Macon County, Illinois.


25 September: Bike the Ridge
Evanston, IL
Bike the Ridge Evanston cycling IL Illinois familyBicycles are not allowed on Ridge Avenue at any other time, so come out and enjoy this non-competitive, City-sponsored special event! Ridge Avenue will be closed to vehicular traffic so bicyclists may ride on a 2-mile stretch of Ridge Avenue, from Howard Street to Church Street. The event kicks off at 9am at the intersection of Ridge Avenue and Howard Street. Children are encouraged to decorate their bikes in advance. Activities will be held along the route. Non-bicyclists are encouraged to walk along the sidewalks of Ridge Avenue and support the bicyclists. Bike-related activities are plentiful.

Get in to Higher Gear for a Tune-Up, so you’re ready to ride!



Road riding doesn’t end with the summer. These rides are a great way to see the brightly colored fall leaves and enjoy exercising in the cooler weather:


October 2016 Cycling Races, Rides & Events


2 October: Pumpkin Pie Ride
Ottawa, IL
The 27th Pumpkin Pie Bicycle Ride, is organized by the Starved Rock Cycling Association. The Ride takes place in scenic North Central Illinois. Routes include but are not limited to Road Rides 25, 45, 63, 100 mile routes, with light traffic and rolling hills. Registration includes: pumpkin pie after the ride, rest stops with fresh baked cookies and other food items, hydration, maps and cue sheets.


2 October: Pumpkin Pedal
Sycamore, IL
Join the fun of the Pumpkin Pedal!! This is a wonderful ride for families and serious riders. This year’s 10-, 20- and 26-mile trail rides will be entirely on the Great Western Trail. The 40- and 62-mile road rides will be on roads. Besides the fun you’ll have and the great people you’ll meet, you’ll be riding to help Special Olympics athletes. Your entry will support year-round training for Illinois athletes with intellectual disabilities.


8 – 9 October: GITy Up!
Rock Island, IL
GITy Up! is bite-sized, overnight bike touring on the Great River Trail along the Mighty Mississippi in western Illinois, from Rock Island to Port Byron and the communities and forest preserves along the way. Inspired by the 450-mile Grand Illinois Trail, GITy Up! is a single overnight, supported bike tour for beginning bike campers, for families, for the expert with restless legs but only a weekend free. You’ll cover 50 miles total of trail-based bike touring spread out over two days and a glorious evening of camping in between. It’s crazy healthy happy fun!


21 – 23 October: 49th Annual Hilly Hundred Bicycle Tour
Southern Indiana
2016 marks the 49th Annual Hilly Hundred Bicycle Tour in beautiful Southern Indiana. Two 50 mile days of riding on country roads over challenging hills. Also 30 mile options. Lunch, sag stops, and entertainment included. Also available: on site camping, dining and local amenities in Bloomington and Ellettsville.




Mechanic-StuartHigher Gear hopes you have a great summer of riding! Don’t get on your bike without a proper cycling helmet, cycling glasses and your Road ID. And always use sunscreen!

Whether you’re racing, riding in a charity event or taking the bikes out for a ride with the family, be sure your bike is in working order.

Get it in to Higher Gear for a Tune-Up, so your bike is ready to ride when you’re ready to ride!


For more event listings, visit Chicago Bike Racing, League of Illinois Bicyclists, Wisconsin Cycling Association, Bicycle Federation of Wisconsin, Michigan Bicycle Racing Association, and League of Michigan Bicylists.


To stay current with local events, sign up for our weekly newsletter. Check back here (from our home page, click Riding/Racing >> Chicagoland Cycling Calendar), as we’ll update our calendar as events are added and dates are finalized. If you or your team have an event not listed here, please contact us and let us know about it.



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Wilmette | 847-256-2330

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