There are lots of century rides, but this one is special. It's a synthesis of a great route, challenging terrain, supportive infrastructure, a wonderful destination and a terrific place to vacation thereafter. Previous participant feedback
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This is a long Ride that needs proper preparation and training. It is also an enjoyable and well-supported Ride. Read our preparation tips.

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This ride could not happen each year without the support of our awesome volunteers. Here are ways you can help.


Join us for the best one day Boston to Provincetown bicycle ride. This is a social ride and requires no fundraising. Even better, it is a weekend happening and a great way to kick off your summer vacation and bicycling season. We are a diverse group of people (mostly gay and lesbian, but all are welcome to the challenge). It is a serious ride, but many who go are also recreational riders who are looking to up their miles. All day long, you will be supported by an outstanding support crew and supplied with all that you need to cross the finish line. So talk it up with your friends and family and register today!


Cyclists on this Ride will be challenged with varying terrain and weather. This is a long Ride that needs proper preparation and training. But, it is also an enjoyable and well-supported Ride. The five rest and refueling stops along the way offer much needed water, food and support. You will have pleasant downhill runs and some seemingly endless roads that may not be as enjoyable to ride. You will see sand dunes, ocean, forest and highways. You will be surrounded by cyclists of varying riding abilities and will find others to ride along with. You will be riding alone at times. You will be in clusters at times.

MassBike promotes a bicycle-friendly environment and encourages bicycling for fun, fitness and transportation. We encourage Massachusetts riders to join MassBike.

Join OutRiders group on FaceBook, so that we can build a community of Riders who may want to form training rides, inquire about rooming in Boston or Provincetown, and offer a way to share experiences and feedback about our amazing event. Everyone is welcome!

Meet Bob Bland, Rider #1

Bob and seven friends started this ride in 1985 as a fun way to complete a one-day ride that ended in Provincetown. There were various other bicycling groups that did this ride in either a one or two-day format. Two friends met the pioneer riders a couple of times along the way, effectively becoming SAG support.

In 1986, after participating in a bike ride in France, interest was expressed in once again planning this "double metric century" ride. This time, the ride was publicized to many of the gay outdoor activity clubs around the country. Sixteen riders participated in the 2nd Annual Boston to Provincetown Ride. The Ride was becoming such a positive experience that it was run a third time in 1987, now with 45 riders. Bob arrowed the route as he rode it, and organized formal SAG stops for the riders. Word continued to spread about this event, and the Ride grew to 80+ riders, then 130+ riders, and was eventually capped at 300. In 2020, the assigned numbers for new riders will begin at 2736.

As the ride grew beyond the ability of one person to manage, an organizing committee was formed. Bob remained the coordinator through 1990, with Peter Smith coordinating the Ride through 1996, and Mark Legere continued the work from 1997–1999. Dan Williams coordinated the ride from 2000 through 2010, upholding many of the traditions that have become hallmarks of this event. The current coordination team consists of Lew Lasher (Rider #23), Jim Gerhard (Rider #98), Sondra Spencer (Rider #220), Arne Buck (Rider #2510), and Quang Le (Rider #2560). There is always room for more on the team. Bob was active in the ride as a rider initially, and as a volunteer as long as he lived in New England. After he moved to Arizona, the ride remained close to his heart up to his death in 2011. We are all the beneficiaries.

And finally, thanks to all those riders and volunteers who have, and continue to, support this incredible journey!