Riding with Harbor to the Bay

Have you always wanted to do a long-distance ride, but never thought you could make it? Well, so have many of the Harbor to the Bay participants! Until joining H2B, a large number of our participants had never ridden more than 10 miles. However, as we cross the finish line, you’ll be elated by your personal accomplishments as well as the impact on your community!

What makes H2B different? The H2B Ride is not a race! Instead, it’s a ride where dedicated people who want to support people living with HIV and AIDS can make a difference. Your actions, and 100% of every dollar you raise, will benefit your community.

What follows are some of the details about the day of the ride, including gear, training, the route, starting locations, and fundraising minimums:

Prepare to ride!

All riders will be required to wear helmets. If you do not have a helmet, you will not be permitted to ride! Your safety is our top concern and this rule will not compromised. Riders are encouraged to have their bikes inspected prior to Ride Day. Please check out our Bike Shop Sponsors for a check up, gear, or any general questions!

Beginning and intermediate riders are also strongly encouraged to wear riding shorts, and use a road or hybrid bike for Ride Day! Riding shorts are padded and prevent chafing, which is a real concern for distance riding.

As for your bike, a mountain bike is not designed for distance riding, and you’ll feel it after 30 miles! So, we recommend you either rent a bike (less than $30 a day) or get “slicks” for your mountain bike, which greatly improve your chances of making it! Or, see if a friend has a loaner bike! We want to be sure you arrive in Provincetown in the best shape possible!

Bicycles, Equipment and Luggage

Harbor to the Bay will coordinate transporting your luggage from Boston to Provincetown. You should clearly label your gear and bring it with you to the Ride Day Registration event.

Your gear will be delivered to the Harbor Hotel in Provincetown, and stored in a secure room until you pick it up. You will need to transport your luggage from the Harbor Hotel to your accommodations. We will make every effort to safeguard your gear but Harbor to the Bay cannot accept liability for any lost or damaged items.


So, how do you prepare to go from riding a few miles to riding over 60, or even 125!? You should begin training as early as possible, at least one month prior to Ride Day. For beginners, start with riding 10 miles, twice a week, for two weeks. Then, increase to 20 miles twice a week, then thirty and higher. You should set a goal of riding 40+ miles prior to Ride Day. And, if you have any concerns, always talk to your primary care provider, to be sure you’re ready!

If you’d like to join us for training, check out the Training Rides page. H2B hosts numerous training rides for riders of all levels. Whether you feel like a trip through the Arboretum, a 40 mile spin along the Minute Man Trail, or a 100 mile “century ride,” we’ve got the training for you.

The Route

The route will be well marked, and we will have maps available for you. You can check out the Route Map online, as well. H2B has used this beautiful route for several years, and has refined it to maximize your safety and enjoyment.

Starting Locations

68-Mile Ride: Boston to Sagamore Bridge – OR – Sagamore Bridge to Provincetown

Those riders who want to challenge themselves to ride 68 miles have the option to start from either Boston or the Sagamore Bridge in Sagamore, MA. Sagamore to Provincetown is the recommended route for beginning cyclists, with less traffic and fewer hills than riding from Boston to Sagamore.

If leaving from Sagamore, you will need to coordinate transportation to the Sagamore Bridge. If you drive, there will be parking at the Commuter Lot.

Harbor to the Bay is not a race, so you can find a group of riders who are moving at a pace that is comfortable for you. There will be pit stops every 15 miles where you can rest, use the restroom, have a snack, and stretch. Each will be staffed by our enthusiastic crewmembers, who can provide you with any assistance.

125-Mile Ride: Boston to Provincetown

Those riders who want to challenge themselves to ride the full 125 miles will start from Boston and ride to Provincetown. This route is recommended for intermediate and advanced cyclists, with some hills. Please note that there are hills past the 100-mile mark, but you can handle them!

There will be pit stops every 15 miles where you can rest, use the restroom, have a snack, and stretch. Each will be staffed by our enthusiastic crewmembers, who can provide you with any assistance.

If you find that you’d like to stop prior to arriving in Provincetown (i.e., ride less than 125 miles,) we will cheer your arrival and coordinate transportation as needed! You are required to ride to the nearest pitstop, and let our crew know that you’d like transportation for the rest of the route. Again, your safety and comfort is our top priority and we’re here to celebrate and support your efforts, no matter how far you go!

Getting Home – Provincetown to Boston

You will be responsible for coordinating transportation from Provincetown back home. Most years, we are able to get a discount for our participants, including bikes and luggage, on ferry service to Boston..

$1000 Fundraising Minimum

The minimum fundraising amount for participation is $1000.00 from each rider. This is a firm minimum, and you will be required to fulfill this amount. But, it’s easier than you think! H2B provides numerous fund-raising opportunities and will help you raise the money. Additionally, if you’re part of a team, and your team’s fundraising total is greater than $1000 for each participant, than your minimum is covered.

$75 rider registration fee

Your $75 rider registration fee will be used to defer the cost of the ride so that 100% of the pledge money raised can go to the beneficiaries. Your registration fee includes:

  • A customizable, personal H2B Donation page at HarborToTheBay.org where all donations will be made without transaction fees
  • A marked, tested route and maps, to ride from Boston to Provincetown
  • A fully-supported route including SAG vehicles, bike techs and repair
  • parts at all major pit stops, and emergency support
  • Dedicated motorcycle safety crew provided by the Moving Violations
  • Breakfast in Boston at the start of the ride
  • Lunch along the route, at the various pitstops
  • Food at the Harbor Hotel, for arriving Riders and Crew
  • Dinner and a T-shirt, provided at the Closing Ceremony