Tap Into the Trails Festival & Oktoberfest 2025

🎉 Tap into the Trails & Oktoberfest 2025 🎉
📍 Downtown Cheboygan & Trail System Access Points & Festival Square.
📅 Saturday, September 27, 2025
🕘 8:00 am - 9:00 pm

🍁 Cheboygan’s Premier Fall Festival is Back! 🍁
Join us for Tap into the Trails & Oktoberfest 2025, a one-of-a-kind celebration of Cheboygan’s stunning trail system and the many ways our community comes alive outdoors!

This family-friendly, trail-loving, beer-sipping, leaf-crunching day is packed with activities for all ages and interests. Whether you walk, run, ride, paddle, or roll—we invite you to explore, play, and unwind along our trail system and in the heart of downtown.

🎯 Festival Highlights Include:

🏃‍♂️ 5k/10k Family Fun Run
🦅 Bird Watching Experience
🚴‍♀️ Guided Bicycle Trail Rides
⛰️ Mountain Bike Experience
🚸 Children’s Trail Activity & Trail Hike
🧘‍♀️ Downtown Cheboygan Morning on Main
Downtown Day
🍂 Fall Foliage Photo Stops
🎶 Live Music Downtown
🍺 Local Craft Beer Garden – Oktoberfest Style!
🎨 Cornhole Tournament
🏆 Games & Contests
👟 Family Trail Treasure Hunt
🐶 Dog-Friendly
🎟️ All Are Welcome!
Some activities and tastings may require a wristband purchase.

Tap into the Trails celebrates what makes Cheboygan special—our natural beauty, our vibrant trail system, and our community spirit. Come dressed for the outdoors or in your best Oktoberfest gear—just don’t miss it!

👉 Stay tuned for the full schedule and interactive trail map!
Follow this event page for updates, vendor spotlights, and previews of all the fall fun.