WNY Winter Hiking Challenge
Welcome to the Western New York Winter Hiking Challenge brought to you by Outside Chronicles. This challenge was created to get people out on the trails during the long WNY winters. Our goal is to encourage people to get outside, embrace the cold, and reap the many benefits of hiking in cold weather. We also want to give back to the trails and have donated over $450,000 to great organizations. Our goal is to promote outdoor activities and help people appreciate the natural beauty of the region.
What’s Included in the Challenge
- NEW Winter Hiking 101 Course – Access to our new online course with registration (a $27 value).
- Challenge Packet – a PDF containing information to get you started, park descriptions, trailhead coordinates, maps, checklists, and more. Check out some sample pages and the 2025 trail list (map view).
- Digital Maps – every location has a digital map you can import into the easy-to-use Avenza maps app.
- Challenge App – an app to track your progress; the app works on iPhone, Android, or in a web browser.
- Challenge Portal – hikers can check trail conditions, access a Google map of hike locations, report a problem, and more.
- Private Facebook Group – participants can join a private challenge Facebook group to ask questions, share photos, and meet your fellow hikers.
- Improved Physical & Mental Wellbeing – it’s a proven fact that getting outside in nature will improve your physical and mental fitness.
- Give Back – a large portion of your challenge registration fee will be donated to organizations doing incredible work in WNY.
New to the Challenge? Check out our Frequently Asked Questions.
Participated in the Challenge before?  Check out Things to Know in 2025
Giving Back
The WNY Hiking Challenge donates a large portion of the proceeds to organizations that promote stewardship of the outdoors, protect the lands we use for recreation, or provide outdoor education for all. This year’s theme is Hiking Trails. We are donating to Buffalo Audubon with special donation to Sadie’s Safe Harbor Canine Rescue. Learn more about this year’s beneficiaries.
Challenge Rules
This year’s Challenge features 32 trails. Hikers need to earn 50 points to receive a finisher patch, sticker, and bragging rights.
- Earn fifty (50) points by completing challenges in our app between Dec. 20, 2025 and March 20, 2026, inclusive.
- Points can be earned by hiking trails, completing stewardship tasks, and other fun challenges!
For Independent Health, please use your Health Extras card like a credit card at checkout.
For Highmark WNY, you will need to use your personal credit/debit card and submit a Wellness Card Reimbursement Claim Form.  Claims can be submitted on the member website. Log in at myhighmark.com and click Manage under Spending Account Balance to access your personal dashboard. Then, select Claims and Claims Activity under the menu in the upper left corner to submit your claim.
How to Get Started
1. Register
Head to our store and purchase the challenge product that fits your situation. We have the following to choose from:
Individual: $25
Family (up to 4 members, +$5 for additional patches): $65
Pet and Owner: $45
Scouts: $20 (Use coupon code scouts25 at checkout, put your troop number in the Order Notes)
2. Download Challenge Packet
After your purchase, you will be emailed a link to the digital Hiking Challenge packet. The packet contains more information about the parks, maps, suggested hikes, landmark locations, and how to sign up for our app.
3. Hit the Trails!
Use the information in the Challenge packet and app to earn 50 points, trails are worth 3, 5, 8, or 15 points depending on difficulty. Get out there and find the landmarks! Each map has a suggested path, but feel free to make your own hike.
Remember to take a garbage bag and leave the trails better than you found them.
4. Complete Challenges
Our app will keep track of your progress. As you complete challenges, your points will increase. Reach 50 points to earn a finisher patch and sticker.
But don’t stop there! You can earn additional in-app badges. Some of the badges will earn you additional stickers! Check out the My Badges section of the app for details.
5. Follow Everyone’s Progress in the App
You can see the Top 100 Leaderboard, check your points, follow a photo feed of submissions, and chat with other hikers; all within the app.
