Sunday, September 20th - Saturday, September 26th

Participants of all ages and abilities welcome!

Portland Trails presents Trail to Prevail: a virtual 10K event to celebrate the prevailing spirit of our community!

The Portland Trails network has been a space for physical and mental wellness for so many during this challenging year. In response to the pandemic and resulting challenges, the Trail to Prevail will celebrate wellness, trails, and the power of community.
It will replace this year's Trail to Ale 10K.

How it works:

Design your own route on the trails and walk, run, bike, rollerblade, unicycle, roll, skip, dance - whatever you'd like! - for 10 kilometers to raise funds for Portland Trails. All ages and abilities are welcome. Check out some 10K routes we've designed to inspire you.

Even if you won't be in the Greater Portland area for the event, celebrate with us from afar by participating on the trails closest to you. Participants are encouraged to share photos and videos of their 10Ks on social media. As a thank you for your participation, you'll receive a free Trail to Prevail buff in the mail.


Also new this year, participants will have the opportunity to fundraise for Portland Trails! 2020 has been, and continues to be, a difficult year for all of us. Because the trails have seen such a sharp increase in visitors this year, we have had to allocate a significant amount of time and resources to trail maintenance. Additionally, without our usual fundraisers and corporate sponsorships, 2020 will be a challenging financial year for Portland Trails, too. If you want to support our year-round trail work, active transportation advocacy, and community-building projects beyond your registration, you will have the option to create a fundraising page that you can share with your family and friends. If you raise at least $100, you will receive a free, limited edition Trail to Prevail t-shirt! Our top six fundraisers will also receive a prize package from local shops and breweries.

If you're participating with a team, you can also fundraise as a team! Team members will receive t-shirts if, collectively, the group raises at least $100 per team member. (For example, once a team of 4 raises $400, each team member will receive a t-shirt.) Our top three fundraising groups will receive a prize package from local shops and breweries for up to four group members.

Event details:

The Trail to Prevail event will be held for a week beginning Sunday, September 20th and ending Saturday, September 26th. Our intention is that participants will have plenty of time to complete their 10K without overcrowding our trails. All funds raised will directly support the Portland Trails network and our work in the Greater Portland community.

Ages 14 and up: $20

Ages 6-13: $10

Ages 5 and under: free

Thank you to our Trail to Prevail sponsors:

T-shirt Sponsor:

At Fidelity, we help over 32 million people feel more confident in their most important financial goals, manage employee benefit programs for over 22,000 businesses, and support more than 13,000 financial institutions with innovative investment and technology solutions to grow their businesses.


Run Sponsor:

At Float Harder, our sensory deprivation tanks will help you to relax your muscles and clear your mind. If you experience chronic pain, enjoy meditation, feel overwhelmed by sensory overload, are looking for that competitive edge, or just want to relax, then treat yourself to a session in one of our float pods or float rooms!


Walk Sponsor:

As a customer of Machias Savings Bank, the focus is on you. We will enhance your banking relationship by working with you to discover your banking needs. We will be there when you need us.


Bicycle Sponsor:

Whether you race, ride the mountains, commute, or enjoy just cruising around your neighborhood, Cyclemania has been your local bike shop and will continue to be for many years to come. Next time you’re in Portland, stop by to check out the latest gear or just chat bikes. 


Accessibility Sponsor:


Whether it's sharing a recipe, getting involved in local activities, looking for caregiving help or getting information on social security, AARP provides our members with a wealth of opportunities to save money, play, learn and volunteer.


Route Sponsors:

No matter how large or small, we are committed to serving and meeting our customers’ needs. We build genuine relationships that last for generations by providing our customers with a differentiated experience, convenient technology, and personalized solutions.


With a successful, innovative, whole human approach to health care, Jade Integrated Health has been the leading integrative health option, for physicians and patients in Portland & Brunswick, ME for over 15 years.


98.9 WCLZ - Where Different is Good


Trail Sponsors:



Interested in sponsoring this event? Learn more here.