7 running and cycling events in Stillwater, Minnesota

Whether you’re a seasoned runner or just love to walk and take in the scenery, SKECHERS Wicked Wine Run is for you! Each course will be held on beautiful properties or various partner vineyards across the country giving you a rare opportunity to view and tour a vineyard like no other. With the option to choose between a 1K or 5K course, or both, there’s something for everyone. Along the 1K course, you’ll find four sampling stations where you can enjoy world-class wines from the partner vineyard. And if you complete the 5K course, there will be a complimentary glass of wine waiting for you at the finish line.

Enjoy access to our post event party where you can enjoy the tunes of a live DJ, eat some delicious food from our food trucks, purchase more wine and play “that’s when we became best friends” games, creating the perfect atmosphere for an evening out with your friends and loved ones. Don’t miss out on the fun-filled event!

Bring a friend, put together a team, or fly solo to meet fellow wine enthusiasts as you sample wines from the vineyard. By participating, you’ll not only be treating yourself to a great time but also supporting our charity partners!

Event details and schedule

For all other details, please visit www.wickedwinerun.com

WELCOME TO THE 6TH ANNUAL BRIDGE THE VALLEY BIKE RALLY

We invite you to ride our sixth annual bike ride on August 9, 2026 sponsored by Stillwater Sunrise Rotary. You will experience the beauty of the St. Croix Valley using our trail systems, roads, and beautiful bridges. This year's event will feature scenic bike rides along the beautiful St. Croix river, with all routes crossing into Wisconsin and back to Stillwater to finish. You also can enjoy great pre-ride snacks, friendly and well-stocked rest stops, and free drinks and live entertainment after the finish.

This year, you have three exciting new options:

• 100 mile Century Ride to test your fitness.

• Family Fun Ride to entertain families with children under 12 on a 5-mile ride across the scenic Stillwater bridges with fun post-ride activities for kids.

• Adaptive registration category for riders who have a physical disability or visual impairment.

As in past years, you also will have your choice of five other ride options, 5 miles, 25 miles, 40 miles, 50 miles, and 70 miles.

Register before June 1 to take advantage of Early Bird discounts! Early Bird entry fees are the same as last year: $40 for adults 19 and older, $20 for youth ages 12 to 18, and free for kids under 12. The Family Fun Ride for families with children 12 and under is only $30. All roads and trails are blacktopped. Pick just one loop from the progressively more challenging options or combine several to fit your age, ability, and interest on the day. This event is a rally (not a race) and your start time depends on the length of ride you are doing.

All rides start and finish at Chestnut Plaza, immediately west of Stillwater’s historic Lift Bridge. The event Support Hub is located next to the Lift Bridge in South Lowell Park. Event information, day-of registration, and a fenced and monitored bike corral will be available. Downtown Stillwater has many attractions and businesses within walking distance of the Support Hub so participants can take in all that Stillwater has to offer. Stick around after the ride for food, drinks, and music in South Lowell Park!

All routes will be supported with SAG and rest stops with refreshments. (Maps and more details about the routes are coming soon.) All rides will be accessible on the innovative Ride with GPS app to help you navigate the routes, and all rides (other than the 70 mile and 100 mile) will be signed.

Finish your ride in beautiful downtown Stillwater. Meet up with your family and friends and top off your ride day with food and drink and live entertainment along the majestic St. Croix River.

Overnight Lodging

Come for the ride, stay for the weekend. Make a weekend of it by booking a room at one of Stillwater's many wonderful hotels and B&Bs . Visit Discover Stillwater HERE to check out options for lodging, dining, and things to do.

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Military Discount

Active duty, reserve, retired, and guard, use the coupon code MILITARY2026 to receive a 20% discount on all rides.

Fundraising and Sponsors

Funds raised from Bridge the Valley support projects like STRIVE, a mentorship for students at Stillwater High School with scholarships available, VESL, a service project that promotes literacy at local elementary schools, “End Polio Now” Campaign, and clean water projects in Nicaragua and Kenya plus many others. The more successful the event, the more financial assistance Stillwater Sunrise Rotary can give out! See our website if you'd like to help us sponsor this ride!

What is Stillwater Sunrise Rotary?

Our club members are dedicated people who share a passion for both community service and friendship. Becoming a Rotarian connects you with a diverse group of professionals who share your drive to give back. Rotary is a global network of 1.2 million neighbors, friends, leaders and problem-solvers who see a world where people unite and take action to create lasting change – across the globe, in our communities and in ourselves. Learn more about Stillwater Sunrise HERE.

Due to commitments made to our charity beneficiaries we are unable to refund any registration or merchandise fees for any reason.

Please know that your dollars are going to many worthy organizations in the greater Stillwater area!

E-bikes are welcome on all routes. E-motos are not allowed.

Helmets are required. Period.

Questions? Contact us at [email protected]