Once you Register
Upon registering, you’ll receive an email confirmation with access to your personal fundraising webpage and all fundraising and training resources. A Best Buddies Challenge Development Associate will be assigned to you. Best Buddies Challenge Development Associates are dedicated to helping Challenge participants meet their fundraising goals.
The Day Before – Friday, May 29, 2026
4:00 – 7:00 PM
Early Packet Pick-up at JFK Library
Columbia Point, Boston, MA 02125
Event Day – Saturday, May 30, 2026
7:00 AM
100-mile ride starts at JFK Library
Columbia Point, Boston, MA 02125
Check-in & breakfast opens at 5:30 AM
7:10 AM
Shuttles depart 100-mile start line to the 55-mile start line in Carver and 20-mile start line in Sandwich.
Boarding starts at 5:30 AM
9:30 AM
5K run/walk starts at Craigville Beach Finish
1040 Craigville Beach Rd., Centerville, MA
Check-in opens at 7:30 AM
55-mile ride starts at CVS Pharmacy in Carver
100 North Main Street, Carver, MA
Check-in & breakfast opens at 8:00 AM
10:30 AM
20-mile ride starts at CVS Pharmacy in Sandwich
65 Tupper Road, Sandwich, MA
Check-in & breakfast opens at 9:00 AM
12:00 PM
Craigville Beach Finish Line showers, massages and luncheon opens and shuttles begin making loops of local Hyannis Port hotels.
1040 Craigville Beach Rd., Centerville, MA
1:00 – 6:00 PM
Post-event party featuring a lobster clambake, open bar, and private concert.
4:30 PM
Early Bus transportation available back to your start line
Boarding starts at 4:00 PM
6:00 PM
After-party ends
6:00 PM
Last Bus transportation available back to your start line
Boarding starts at 5:30 PM
6:00 – 8:00 PM
Post-event VIP reception for top fundraisers at the home of Anthony K. Shriver
The day after – Sunday, May 31, 2026
9:00 AM
Bus transportation from Hyannis Port hotels available back to your start line
Please be outside your hotel lobby no later than 8:30 AM to board your shuttle
As part of the five-star experience, the Best Buddies Challenge provides our cycling participants shuttle transportation to the 55 mile or 20 mile starts lines. We’ll bring your bag down to Hyannis Port so you’ll have a change of clothes waiting for you at the finish. After the party, we’ll get you to your hotel in Hyannis Port or back to your start line. And if you stay in Hyannis Port after the event, we’ll get you and your bike back to your start line on Sunday following the event. You take the Challenge, we’ll handle the rest.
Saturday Shuttles
7:10 AM
Shuttles depart the 100-mile start to the 55-mile start in Carver and the 20-mile start in Sandwich.
Boarding starts at 5:30 am
12:00 PM
Finish line shuttles begin making loops of Hyannis Port hotels for those participants wishing to visit their hotel room prior to the event after party and concert.
4:30 PM
Early shuttle option for riders who selected to go back to either the 100, 55 and 20-Mile Start Lines on Saturday. Expected to arrive in Boston at approximately 6:00 p.m.
Boarding starts at 4:00 pm
6:00 PM
Last shuttle option for riders who selected to go back to either the 100, 55 and 20-Mile Start Lines on Saturday. Expected to arrive in Boston at approximately 8:30 p.m.
Boarding starts at 5:30 pm
Sunday Shuttles
9:00 AM
Shuttles begin picking up riders from Hyannis Port hotels departing for the 100, 55 and 20-mile Start Lines.
Please be outside your hotel lobby no later than 8:30 AM to board your shuttle.
Start Lines
100-Mile Start Line:
100-Mile Ride Starts: 7:00 AM
JFK Library
Columbia Point, Boston, MA 02125
55-Mile Start Line:
55-Mile Ride Starts: 9:30 AM
CVS Pharmacy in Carver
100 North Main Street, Carver, MA 02330
20-Mile Start Line:
20-Mile Ride Starts: 10:30 AM
CVS Pharmacy in Sandwich
65 Tupper Road, Sandwich, MA 02563
5k RunWalk Start Line, Bike Ride Finish Line, & Victory Celebration:
5k RunWalk Starts: 9:30 AM
Craigville Beach Hyannis Port
Craigville Beach Road, Centerville, MA 02632
Rest Stops
Rest Stop 1 (Mile 16.2, Miles to go: 83.7)
Wompatuck State Park Visitors Center, 204 Union St., Hingham, MA 02043
Cyclists arrive: 7:48 AM– 8:36 AM
Stop closes: 9:00 AM
Rest Stop 2 (Mile 38, Miles to go: 62)
Duxbury Senior Center, 10 Mayflower St., Duxbury, MA 02332
Cyclists arrive: 8:54 AM– 10:48 AM
Stop closes: 11:15 AM
Rest Stop 3 (Mile 55, Miles to go: 55)
CVS Pharmacy (Also 50-mile start line), Carver Shaw’s Plaza, 100D N. Main St., Carver, MA 02330
Cyclists arrive: 9:35 AM – 12:00 PM
Stop closes: 12:15 PM
Rest Stop 4 (Mile 64, Miles to go: 36)
College Pond Bath House, Myles Standish Forest, Lower College Pond Rd., Plymouth, MA 02360
Cyclists arrive: 10:12 AM– 1:24 PM
Stop closes: 1:45 PM
Rest Stop 5 (Mile 80, Miles to go: 20)
CVS Pharmacy (Also 20-mile start line), 65 Tupper Road, Sandwich, MA 02563
Join us for a meet-up!
Prior to our main event, we host a number of group rides, happy hours and other meet-ups held throughout the year.