2026 Bicycles & Bluegrass

Distances and entry

• 9:00 AM Sunday Short Option Ride with Kate Courtney | She Sends Foundation — Free
• 9:00 AM Sunday Medium Option — Free
• 9:00 AM Sunday Long Option — Free
• 11:00 AM Female Sports Science Brunch & Panel | She Sends Foundation x USA Cycling Foundation — Free
• 9:00 AM Saturday Short Option — Free
• 9:00 AM Saturday Long Option — Free

About 2026 Bicycles & Bluegrass

WELCOME TO BICYCLES & BLUEGRASS 2026

Bicycles & Bluegrass is the USA Cycling Foundation’s largest annual fundraiser, bringing our community together for an unforgettable weekend of riding, connection, and support for the future of American cycling.

Join us November 7–8 at Rosewood Sand Hill for a weekend of riding some of the Bay Area’s most iconic cycling roads alongside USA Cycling athletes, Olympians, supporters, and friends of the cycling community.

Saturday and Sunday rides will start and finish at Rosewood Sand Hill, with multiple route options to choose from. Please review the route details carefully and register for the option that best fits your riding ability and goals for the weekend.

SATURDAY OPTIONS

Saturday rides depart at 9:00 AM from Rosewood Sand Hill.

• Saturday Short: 27.7 miles | 2,797 feet of climbing
  Our more approachable Saturday option, featuring the roads surrounding Woodside with plenty of climbing and descending along the way.

• Saturday Long: 63.1 miles | 6,770 feet of climbing
  Our most challenging ride of the weekend. This route heads from Woodside out to Pescadero and is best suited for experienced riders comfortable with sustained climbing, descending, and a longer day in the saddle.

SUNDAY OPTIONS

Sunday rides depart at 9:00 AM from Rosewood Sand Hill.

• Sunday Short Option Ride with Kate Courtney: 15.6 miles | 877 feet of climbing
  Join World Champion, Olympian, professional cyclist, and She Sends Foundation founder Kate Courtney for our shorter Sunday ride. Riders can also register for the Female Sports Science Brunch & Panel following the ride from 11:00 AM–12:00 PM at Rosewood Sand Hill. The brunch and panel is co-hosted by She Sends Foundation, has a capacity of 50 guests, and requires registration.

• Sunday Medium: 27.7 miles | 2,797 feet of climbing
  A solid final ride of the weekend featuring a mix of rolling terrain, climbing, and descending through the roads surrounding Woodside.

• Sunday Long: 45 miles | 5,031 feet of climbing
  Our most challenging Sunday option, with sustained climbing and descending throughout the ride. This route is best suited for experienced riders comfortable with the distance and elevation.

• 11:00 AM Female Sports Science Brunch & Panel | She Sends Foundation x USA Cycling Foundation
  Join Olympian and World Champion Kate Courtney for a brunch and a conversation with leading Female Sports Science experts:

  • Dr. Emily Krauss - Clinical Assistant Professor, Primary Care Sports Medicine, Stanford Children’s Orthopaedic and Sports Medicine Center

  • Dr. Rochele Pojednic - PhD, EdM, FACSM, Chief Science Officer at Restore Hyper Wellness and Founder of Strong Process Education

  • Michelle Chang - Senior Director of Product, Strava

  • Kate Courtney - World Champion, Olympian, professional cyclist for FDJ-SUEZ, and founder of She Sends FoundationThe brunch and panel is co-hosted by She Sends Foundation, has a capacity of 50 guests, and requires registration.

WHAT TO BRING

All riders should come prepared with:

• Helmet

• Cycling shoes

• GPS/navigation device with your registered route downloaded

• Valid ID

• Your bike, unless you reserve a Specialized demo bike

We will provide water bottles, water, ride fuel, and snacks throughout the weekend.

If you are riding a Specialized demo bike, please still bring your own helmet, cycling shoes, and valid ID. We will have SPD-SL and flat pedals available, or you may bring your own pedals if preferred.

SPECIALIZED DEMO BIKES

Thanks to Specialized, a limited fleet of Tarmac and Roubaix bikes will be available for Bicycles & Bluegrass guests to ride throughout the weekend.

After selecting your Saturday and Sunday rides, you’ll be asked toward the end of the registration process whether you’ll be bringing your own bike or would like to reserve a Specialized demo bike. Demo bikes are limited and available on a first-come, first-served basis.

Demo bikes will be available for pickup Saturday morning. If you are registered to ride both Saturday and Sunday, you’ll keep your assigned bike for the weekend.

No bike swaps will be available once bikes are assigned. The bike you reserve will be yours for the ride(s) you’re registered for.

ROUTE NAVIGATION & GPS

Please download the route you register for to your personal GPS device before arriving for your ride.

Riders are responsible for bringing their own GPS device and having the appropriate route downloaded and ready to navigate. We strongly encourage every rider to have the route available on their own device, even if you plan to ride with a group.

RIDE SUPPORT

All Bicycles & Bluegrass rides will include on-course support, including SAG and mechanical assistance.

Routes take place on open roads. Riders are expected to follow all traffic laws, ride responsibly, and be prepared to navigate their registered route.

FUEL & HYDRATION

Nutrition, water, and ride snacks will be provided for riders throughout the weekend.

We’ll have fuel and hydration available before the rides and additional support along the routes. If you have specific nutrition needs or products you prefer to use while riding, we recommend bringing those with you.

We look forward to riding with you in Woodside and celebrating another incredible year of American cycling!