Okemo Valley begins its graceful shift from lush summer landscapes to the vibrant hues of fall. Warm days still invite outdoor adventures—hiking, biking, and exploring our scenic backroads—while cooler evenings hint at the season ahead.
Farmers markets brim with late-summer produce and early autumn harvests, and our towns stay lively with music, festivals, and local charm. Maple woods whisper of the sweetness to come, and the night sky still dazzles with the Summer Triangle—Vega, Deneb, and Altair—perfect for stargazing.
Keep an eye on the Vermont Foliage Report to catch peak color and plan your perfect fall getaway.
Special Events Every Fall:
Vermont Cheese Week – Mid-September
THE GRAFTON HISTORICAL SOCIETY FOOD & ANTIQUE TRACTOR SHOW
September 5, 2026 in Grafton
WELLWOOD ORCHARDS HARVEST FESTIVAL
September 5, 2026 in Springfield
PLYMOUTH FOLK AND BLUES FESTIVAL 2026
September 5-6, 2026 in Plymouth
TRIQUEST GRAVEL TRIATHLON
September 12, 2026 in Plymouth
52ND ANNUAL CHESTER FESTIVAL
September 19-20, 2026 in Chester
WELLWOOD ORCHARDS ANNUAL CAR SHOW
October 10, 2026 in Springfield
LUDLOW ROTARY CLUB CHILI COOK-OFF
October 10, 2026 in Ludlow
OKEMO’S ANNUAL FALL INTO WINTER FESTIVAL
October 11, 2026 in Ludlow
Fall Outdoor Adventures:
Hiking: Explore trails like the Healdville Trail or Okemo Mountain State Forest and enjoy being immersed in the fall foliage. Check the Hiking Guide HERE.
Biking: Navigate the newly thawed roads of Okemo Valley. There are so many peaceful backroads to explore in the region. Check out this guide. Please note that most Mountain Bike trails may be closed to protect the paths during the muddy season.
Fishing: Cast a line in the Black River or nearby lakes for a peaceful day by the water. Check out this resource for places to explore!
Golf: Hit the greens at local golf courses surrounded by stunning fall landscapes, including Fox Run Golf Club & Crown Point Country Club.
Picnicking: Pack a basket and relax in serene spots like Buttermilk Falls or scenic mountain meadows.
Paddling: Get out your kayak, canoe, or paddleboard and go for a peaceful paddle on one of the many lakes in the region: Lowell Lake State Park in Londonderry, Gale Meadows Pond in Londonderry, Lake Ninevah in Mount Holly, Spring Lake in Shrewsberry, Woodward Reservoir in Plymouth, Echo Lake in Plymouth, plus Camp Plymouth State Park has boat rentals through mid-October.
Horseback Riding: Enjoy the magnificent fall scenery via a horseback ride through the countryside with the local equestrian service, Mountain View Ranch.
Phototaking: There are so many scenic spots around Okemo Valley that become even more photogenic in the fall. Check out this local photographer’s guide to the best photo-taking spots in Okemo Valley.
Relaxation
Enjoy a spa day + massage: Unwind with a spa day – visit the Castle Hill Resort and Spa. Indulge in a luxurious massage or soak in a hot tub. Visit Calm Moments Massage Studio, and the unique herbal apothecary for a therapeutic massage at Thyme and Again Apothecary.
Scenic drives: Take a leisurely drive with the windows down through the valley to appreciate rolling mountains and fresh greenery. You’ll find lots of fun spots along the Route 100 Scenic Byway – bring a picnic!
Swim & Fitness: Check out the Spring House Pool & Fitness Center schedule.
Shop, Stay, Play, and Dine in Okemo Valley
After a day of fun, a wide range of accommodations are available to suit every preference, from beautiful inns and charming bed-and-breakfasts to elegant hotels and luxurious resorts.
Savor delicious dining options, whether you’re in the mood for a casual meal or a fine dining experience. From romantic candlelit dinners to family-friendly eateries, there’s something for everyone. (Browse Dining Guide Here).
Additionally, find unique souvenirs and treasures while visiting local shops and exploring the arts & culture.
Whether you’re hiking through shaded glens, biking along the scenic Route 100 Byway, or browsing a farmers market in a historic village square, Okemo Valley is a celebration of connection—between people, place, and the beauty of the moment.