Discover Okemo Valley: Late Summer into Fall
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.
Scroll down for our Live Music Concerts and seasonal events!
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Outdoor Adventures for Summer
- Hiking: Explore trails like the Healdville Trail or Okemo Mountain State Forest and enjoy blooming wildflowers. Check the Hiking Guide HERE.
- Biking: Take a scenic bike ride along the picturesque roads or try mountain biking on forest trails. Check out bike routes HERE or also Ludlow Area Sports Trails (L.A.S.T.) for a local trail map at the bottom of their website.
- 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!
- Picnicking: Pack a basket and relax in serene spots like Buttermilk Falls or scenic mountain meadows.
- Kayaking and Canoeing: Paddle your way through lakes or rivers for a tranquil adventure all around the region. Local sports stores have boat rental opportunities during summer time.
- Golfing: Hit the greens at local golf courses surrounded by stunning landscapes, including Fox Run Golf Club and Crown Point Country Club.
- Horseback Riding: Enjoy a scenic ride through the countryside with local equestrian services, including Horses for Hire and Mountain View Ranch.
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 Songbird Wellness.
- Scenic drives: Take a leisurely drive through the valley to appreciate the change in seasons with summer right around the corner. You’ll find lots of fun spots along the Route 100 Scenic Byway – bring a picnic!
- Yoga, group fitness classes + retreats: Jump into a rejuvenating yoga class and more with DG Body Works, or check out the Spring House schedule.
Special Events
- Wellwood Orchards Harvest Festival – August 30
- Grafton Historical Society Food & Antique Tractor Show – August 31
- Plymouth Folk & Blues Festival – August 30-31
- Chester Fall Festival – September 20-21
- Peru Fair – September 27
- Tap to Table: An Autumn Market – October 5
- The Ludlow Rotary Club Chili Fest – October 11
- Mount Holly Cider Days – October 11-12
- Okemo Fall into Winter Annual Celebration – October 12
For more live music, special events and fun things to do – visit our Events Calendar!
Shop, Stay, Play, and Eat 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, explore local shops and arts & culture. Find unique souvenirs and treasures, and visit fun shopping destinations like the Vermont Country Store in Weston.
As the days grow longer, the valley pulses with life. Don’t miss the 5th Annual Best of Vermont Summer Festival, happening August 23–24 at Okemo Field in Ludlow. This milestone celebration features live music, artisan markets, food and drink tastings, kids’ activities, and special performances to mark the occasion.
Throughout the season, local gems like the Hall Art Foundation in Reading host exhibitions such as Pop Perspectives, while Billings Farm & Museum offers nostalgic events like Moos and Brews and the Antique Tractor Day.
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 in summer is a celebration of connection—between people, place, and the beauty of the moment.
Love live music?
Lucky for you, there are all types of local concerts to enjoy all summer. Here are all the places to go to hear live music throughout the Okemo Valley:
Cavendish: Concerts on the Green (Wednesdays)
Chester: Summer Music Concert Series (7PM Thursdays July 31)
Mount Holly: Music on the Green (6:30-8PM Thursdays)
Shrewsbury: Meeting House Concerts (6-8PM Fridays)
Ludlow: Jackson Gore Summer Music at Okemo (5:30-8:30PM Fridays)
Weston: KinHaven Music School Concerts (selected Saturdays & Sundays)
Londonderry: Saturday Deck Sessions and Concerts at Magic (most Saturdays)
Grafton: Grafton Coronet Band (selected Saturday & Sundays)
Ludlow: Summer Bandstand Concerts (6:30-8PM Sundays)
Plymouth: Grace Coolidge Musicals (selected Sundays)
Weston: Sundays on the Hill (4PM Sundays)
Thinking about a new home or a home away from home?
Discover the charm of Okemo Valley with our expert real estate partners! Whether you’re seeking a peaceful retreat for a weekend getaway, a short-term rental for seasonal adventures, or a forever home nestled in this picturesque region, our top guides are here to help.
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