There’s just something special about September in Killington. Summer crowds begin to fade, crisp mountain air starts to settle in, and the first hints of Vermont’s famous fall colors appear across the Green Mountains. At the same time, many of Killington’s favorite warm-weather activities are still going strong, giving visitors the chance to hike, bike, golf, ride the gondola, attend local events, and simply enjoy being outside.
September offers a little bit of everything, whether you’re planning a long weekend or have the flexibility to settle in for an extended stay. Here’s why it might just be one of the best months to plan a Killington getaway.
Enjoy the Start of Fall in Killington
September is a beautiful transition month in Vermont. Early in the month, the mountains are still predominantly green and summer activities remain in full swing. As the weeks progress, cooler temperatures arrive and the landscape gradually begins its transformation toward fall.
The fall foliage typically starts to show off starting around mid-September, when maples at higher elevations start turning orange and red while the valleys below remain green. Peak foliage usually arrives in early October, but late-September visitors get to experience the beginning of the show—and often with fewer leaf-peeping crowds.
Pack a few layers, grab your camera, and get ready to experience that unmistakable Vermont fall feeling.
Take a Scenic Gondola Ride
One of the best ways to take in the changing landscape is aboard the K-1 Express Gondola. The gondola travels 1.25 miles to Killington Peak, bringing visitors to Vermont’s highest lift-serviced summit.
Once you reach the top, you can enjoy sweeping views of the Green Mountains, visit the Peak Lodge, or explore nearby hiking trails. As September progresses and the first fall colors begin appearing at higher elevations, the ride becomes even more spectacular.
For 2026, the K-1 Gondola is open for scenic rides through early October, making this a great addition to your fall itinerary.
Hit the Hiking Trails
Cooler September temperatures make this an excellent time to hike around Killington and the Green Mountains. You’ll find more than 15 miles of designated hiking trails at Killington Resort, along with access to sections of the Appalachian Trail and Long Trail.
Some of the best fall hikes in Killington include the Deer Leap Overlook for quick panoramic views, Thundering Falls for an accessible waterfall walk, Kent Pond for glassy foliage reflections, and the rugged Bucklin Trail or Sherburne Pass leading to high-peak summit vistas.
Whether you’re looking for a leisurely walk through the woods or a more challenging climb with panoramic views, September offers comfortable conditions and beautiful scenery. Later in the month, you’ll also begin seeing splashes of fall color along the trails, which is such a treat!
Go Mountain Biking
Ski season may still be a couple of months away, but that doesn’t mean the lifts aren’t getting plenty of use.
Killington Bike Park features more than 30 miles of lift-serviced terrain with trails suiting a variety of skill levels. The bike park continues operating throughout September, weather and conditions permitting, so you can spend the day exploring the mountain on two wheels instead of skis.
September is particularly fun for mountain biking in Killington, as cooler temperatures arrive and fall begins transforming the surrounding forest.
Play a Round of Golf
Before Vermont trades its fairways for ski trails, take advantage of the final weeks of golf season. Killington Golf Course is an 18-hole championship course surrounded by beautiful Green Mountain scenery. Nearby Green Mountain National Golf Course, rated the #1 public course in Vermont, is another excellent course to play in September.
September’s cooler weather can make for a comfortable day on the course, and the changing landscape adds an extra dose of Vermont beauty to every round. Learn more about the top 5 golf courses near Killington!
Spend a Day at the Adventure Center
Traveling with kids—or just looking to embrace your adventurous side? Killington’s Adventure Center continues operating on select days throughout September (closing in early October).
Depending on current operations, activities may include the Beast Mountain Coaster, zip lines, ropes courses, climbing attractions, and more. The Adventure Center is an easy way to add a little excitement to a Killington fall getaway before winter arrives.
Explore the Area on an ATV Tour
For a different way to experience the Green Mountains, head out on a guided ATV/UTV adventure with ATV Vermont. Located just outside Killington in West Bridgewater, ATV Vermont offers guided one- and two-hour mountain tours in Polaris RZR side-by-sides, taking you along mountain trails to scenic viewpoints and some of the area’s peaks.
September is an especially fun time to hit the trails, with comfortable early-fall weather and the first hints of changing foliage adding to the scenery. This is a great addition to a September getaway for families, couples, or groups looking to add a little more adventure to their Killington itinerary.
Don’t Miss These September Events in Killington
September also brings some of Killington’s most anticipated events of the season!
Cooler in the Mountains Concert Series
Summer isn’t quite over on Labor Day weekend. The final 2026 Cooler in the Mountains concert is scheduled for September 5, featuring Remember Jones at the Bear Mountain Base Area.
This free concert series combines live music, food, drinks, and mountain scenery for one last celebration of summer.
Killington Spartan Race
Ready for a challenge? The Killington Spartan Race returns September 19–20, 2026 at Killington Resort.
Known for taking full advantage of the mountain’s rugged terrain, the weekend features multiple race formats, including the Ultra, Beast, Sprint, and a Kids Race. Even if you’re not competing, the event brings plenty of energy and excitement to town.
Killington Brewfest
Close out the month with one of Killington’s favorite fall traditions. Killington Brewfest celebrates its 30th anniversary on September 26, 2026, at Pico Mountain.
Visitors can sample craft beers while enjoying live music, local vendors, activities, and the beautiful backdrop of the Green Mountains. With fall colors beginning to emerge around the region, Brewfest is a fitting way to welcome autumn in Vermont.
Want to stay as close as possible to the Brewfest? Check out our Pico Mountain rentals here.
Stay for the Weekend – Or Stay for a Month
With so much happening throughout September, you may find that a weekend simply isn’t enough.
The Killington Group offers a wonderful selection of professionally managed vacation homes and condos where you can settle in and experience the mountains at your own pace.
Instead of squeezing everything into a few days, you can enjoy leisurely mornings, work remotely when needed, explore new trails, attend September events, and watch the landscape gradually transition from summer green to fall color.
Our vacation rentals provide the comforts that make longer stays easy, including fully equipped kitchens, comfortable living spaces, WiFi, and room to spread out.
Take Advantage our Our Killington Monthly Rentals
September is also an excellent time to consider an extended stay in Killington.
In addition to nightly vacation rentals, The Killington Group offers special rates on select Killington monthly rentals during the warmer months. One-bedroom monthly condo rentals start around $1,500 per month, while three-bedroom condos start around $3,000 per month, depending on the property and availability. Discounted weekly rates may also be available.
A month-long September stay gives you time to truly experience the season and watch the transformation to fall. Arrive while summer activities are still running, enjoy events throughout the month, and watch as the first fall colors begin spreading across the mountains—all while having a comfortable Killington home or condo to call your own.
Monthly rentals are particularly convenient for remote workers, couples, empty nesters, families with flexible schedules, or anyone who simply wants to slow down and experience Vermont beyond a quick vacation.
Plan Your September Getaway with the Killington Group
September offers the best of both worlds in Killington: the outdoor adventures of summer paired with the crisp air, changing scenery, and events that signal the beginning of fall.
Spend your days hiking, mountain biking, golfing, riding the gondola, or attending some of Killington’s signature September events. Then come home to a comfortable vacation rental where you can relax and recharge for another day in the Green Mountains.
Whether you’re visiting for a few nights or making Killington home for the month, The Killington Group has vacation homes and condos to fit your stay. Browse our Killington vacation rentals or explore our discounted monthly rentals and start planning your September escape to Vermont.
