Late Season Riding Tips
September 27, 2025

Late Season Riding Tips

Ride Smarter, Stay Warmer, and Catch the Best Views This Fall


Late Season Riding Tips


1. Layer Up Smartly
Fall weather in Vermont can swing from sunny 60s to brisk 40s in a single ride. Start with moisture-wicking base layers, add a breathable mid-layer, and keep a packable shell handy for wind or surprise showers.


2. Adjust Your Ride Times
With shorter days, mornings can be chilly and evenings arrive sooner than you think. Plan your rides for late morning to mid-afternoon when temps are most comfortable—and bring a light for safety if you push it close to dusk.


3. Tire Choice Matters
Fallen leaves can hide roots, rocks, and slick patches. Slightly wider tires with good tread will give you the extra grip and confidence you need.


4. Respect Trail Closures
As the season winds down, sections of trail may be closed for maintenance. Always check the Kingdom Trails map and updates before you head out.


5. Don’t Forget the Views
Late season riding is about more than just the miles—it’s about the breathtaking scenery. Take breaks, snap photos, and soak in the last burst of color before winter sets in.


Trail Highlights for Fall


If you’re riding in October, here are a few must-hit trails that really shine this time of year:

  • Heaven’s Bench – Famous for its panoramic views, this spot offers some of the best foliage overlooks in the Kingdom.
  • Sidewinder – Fast and flowing, this trail is even more fun with a carpet of golden leaves under your tires.
  • Pete's Dragon – An absolute classic. Its swooping berms and rollercoaster feel make for an unforgettable last ride.
  • Kitchel – A favorite for all levels, this flowy gem will leave you grinning from start to finish.
  • Fox Run – Cool, shaded, and dreamy with late-afternoon light filtering through, this trail feels magical in the fall.


Stay Wild: Extend Your Adventure


Looking to maximize your late-season trip? The Wildflower Inn is offering a special deal October 17–31, 2025:

👉 Book one night, get the second FREE


Use code:
ONEFINALRIDE when booking.



It’s the perfect way to enjoy one last fall ride, cozy up after the trails, and wake up to those sweeping Darling Hill views.


Ready for One Final Ride?


Don’t let the season slip away—get out there, ride the trails, and savor the final colors of autumn in Vermont.



The Wildflower Inn's Blog!

Our goal is simple: Make your experience memorable, support your interests, and broaden your smile. Everyone is welcome. We want you all to feel it and to leave our property believing it.

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