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.

The Western New York Winter Hiking Challenge is designed to give people an opportunity to visit new local parks and explore new trails.  Along with hiking the trails, the challenge material will educate participants on parks’ history and local tree species to spot while on the trail.

There are 16 parks, each with a unique landmark. The landmarks include waterfalls, ruins, bridges, water features, and trees. Each park has a highlighted “Suggested Trail” that takes you past each Challenge landmark.  Feel free to explore other trails after you have found the landmark. Photos at each landmark will serve as proof of trail completion.

There are 16 hikes to choose from, each with a unique landmark.

We are fundraising for several organizations that help maintain our trails and keep us safe. These organizations include: Finger Lakes Trail Conference, Foothills Trail Club, Crescent Trail Hiking Association, and NFSAR. Pet registrations will be donated to Sadie’s Safe Harbor Canine Rescue.


  1. Complete eight (8) of sixteen (16) trails between December 21, 2023 and March 19, 2024, inclusive.
  2. Take a selfie at the Challenge landmark at each park.
  3. Upload your picture to the submission page.
  4. (Optional) Post your picture to WNY Hiking Challenge Group or on Instagram. (use hashtags #HikeWNY and #WNYHikingChallenge. Be sure to tag @outsidechronicles).

Complete 8 Trails for: a patch, a sticker, a number, and bragging rights!

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.

1. Register

Complete the registration form and submit your registration fee of $23*.

* The registration fee is used to cover the cost of Challenge prizes (patches and stickers) and expenses. All profits will be donated to several organizations that help maintain our trails and keep us safe . Pet registrations will be donated to Sadie’s Safe Harbor Canine Rescue.

2. Download Challenge Packet

After your registration and payment have been verified, you will be e-mailed a link to the Winter Hiking Challenge packet. The packet contains more information about the parks, maps, suggested hikes, and landmark locations.

3. Hit the Trails!

Use the information in the Challenge packet to choose eight (8) trails. Get out there and find the landmarks! Each map has a suggested path, but feel free to make your own hike.

There will be a BONUS for people who want to complete ALL sixteen (16) trails and the BONUS Trail.

Remember to take a garbage bag and leave the trails better than you found them.

4. Upload Your Photos

To complete your Challenge requirement, you will need to upload your selfie to https://outsidechronicles.com/upload.

We love to see your photos and stories! Post your pictures to the WNY Hiking Challenge Group or tag @outsidechronicles on Instagram. Use the hashtags #HikeWNY and #WNYWinterChallenge. You might even see your pictures and stories featured on our channels!

5. Follow Everyone’s Progress on the Challenge Board

Follow the Outside Chronicles Facebook Page for weekly updates.

Check the the Live Challenge Board regularly.

6. Get some 2023 WNY Hiking Challenge Merch


What does the WNY Hiking Challenge Packet contain?
When you register, you will get the complete Challenge rules, a description of this year’s Challenge beneficiaries, a map and description for every hike with links to a digital map to use with Avenza Maps, check out a few sample pages here.

How long and hard are the hikes?
Most hikes are between 3-5 miles with a couple of exceptions that are 8-10 miles. You can always choose not to do those hikes. We rate the hikes as easy, moderate, and strenuous. You may see an easy hike that is 3.5 miles long and a moderate hike that is 3 miles long, the difference is the moderate hike will have more elevation. You can complete the challenge hiking all easy and moderate hikes. Start with the easy hikes and you will quickly be tackling moderate hikes.

Do you offer gift certificates?
Yes, we sell gift certificates for individual registrations in our store at https://outsidechronicles.com/product/gift/

Are there any family discounts?
Yes, the family rate is $65 and entitles the family to up to 6 patches (including pets) upon completion of the Challenge. Just select Family at registration. Families will only need to upload one group picture.

Although we want all family members to go on every hike, we understand that things happen and this may not always be possible. We ask that most family members be present on a majority of trails. And those family members that show up for every hike can hold the patch over the slackers, just kidding!

Is the challenge family friendly or good for young children?
We have had many families and children of all ages complete the challenge. There are many hikes that are very doable with young kids, they will surprise you. Just make sure there is ice cream after the hike. Also make sure the young ones are properly hydrated and have some snacks for the trails. And remember, it is all about getting outside together. If you have a meltdown and don’t make it to the challenge landmark, no problem, it counts!

I get an error that my e-mail address is in use when I register my child or pet?
Sorry, but the registration and upload system requires a unique ID.  Due to previous issues encountered, I am requiring  a unique e-mail address.  There are several free e-mail solutions from Gmail, Yahoo, and Outlook.  I would suggest setting up a free e-mail address for your child or pet and turn on forwarding to your e-mail account.

Are there discounts for scouts?
Yes, registered Girl Scouts and Scouts BSA will receive a $8 discount. Scout registration is $15. Select the scouting organization at registration.

Do I need to register by December 21?
No, you can register anytime between now and March 19, 2024. You need to complete 8 trails by March 19, 2024.

Are dogs welcome at the Challenge?
Absolutely, they can even register and earn a patch. Proceeds from pet registrations benefit Sadie’s Safe Harbor Canine Rescue. Please follow each parks’ rules when you bring your dog (i.e. they must be licensed, kept on a leash and you must clean up after them).

Our registration system requires a unique e-mail for each registered user including our 4-legged friends. If you do not have a secondary personal e-mail address, we suggest setting up a Gmail or Outlook e-mail account and forwarding it to your primary account.

Where can I rent snowshoes?
There are several locations to rent snowshoes in WNY. When you register, the PDF packet has a list of options.

Do I need any special gear?
You will need proper winter layering and the 10 EssentialsSnowshoes and microspikes are strongly recommended when conditions dictate. I suggest investing in mircospikes first, then snowshoes. You will have many more days where microspikes come into play. There are sections of Artpark, Conklin Gully and Chestnut Ridge where microspikes are necessary due to ice and steep terrain.

We suggest someone in your group carry the 10 Essentials on every hike. Every hiker should have a headlamp and whistle at all times. We have a Resources page with checklists and links to our instructional videos. 

How do I not get lost on the trails?
The Challenge Packet contains QR codes to download live maps to Avenza Maps. We have created two tutorial videos for Challenge participants. The first video shows you how to import maps and use basic features. The second video shows you how to use Avenza Maps while on the trail. We also highly suggest taking a paper map and learning basic map and compass skills. We have videos to help you there too!

You mentioned that a book acted as the inspiration for these Challenges?
Correct, the book is out of print, but you may be able to find it used on Amazon or at the library. The book is Secret Places: Scenic Treasures of Western New York and Southern Ontario by Bruce Kershner.

The late Bruce Kershner was a great conservationist and advocate for places like Reinstein Woods and Zoar Valley. *He was also my wife’s high school teacher.

Good news, there is an updated version of Secret Places of Western New York written by Jennifer Hillman and William McKeever. The new version includes some of Kershner’s Secret Places and some new ones taken from his notes. It is a very well done tribute to the original book.

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