GSW Seacoast Century WeekendHampton, New Hampshire - September 22-23 1 of 7
Get an up-close look at the underrated scenic coastlines of Massachusetts, New Hampshire and Maine. Registration takes care of both days of riding, though you can choose one or the other or do a different distance each day.
Tyranena Oktoberfest Bike RideLake Mills, Wisconsin - October 6 2 of 7
The Tyranena Brewing Company puts on this annual event, with 25-, 50-, and 75-mile routes. After the ride, cyclists get two drink tickets for beer, as well as a tour of the brewery and live music.
Burnt Mountain Bicycle RideJasper, Georgia - October 7 3 of 7
Just 60 miles north of Atlanta, this ride is among the many of activities in the Georgia Marble Festival, home of the Georgia State Bluegrass Championship.
Hilly Hundred Weekend Bike TourEllettsville, Indiana - October 19-21 4 of 7
This ride is designed for experienced touring cyclists, but with tons of fun thrown in. A costume contest, live bands and an untraditional chicken option at rest stops is just a few of the charming quirks.
Tour de LeavesTryon, North Carolina - October 20 5 of 7
Located in the foothills of the Blue Ridge Mountains, this ride takes place in conjunction with the Tryon Arts and Crafts Fall Festival and its many activities.
The Boneshaker Bicycle FestivalLa Conner, Washington - October 26-27 6 of 7
Inspired by Halloween, this ride has tons of sideshows, including a kids parade, bike decorating, bike safety rodeo, live music, raffles and prizes.