Scenic Vermont - Okemo Valley Seasonal Guide 🍁🥾

photo by Russ Hurlburt

Discover Okemo Valley: Late Fall!

Okemo Valley begins its graceful shift from lush summer landscapes to the vibrant hues of fall.

Late summer & early fall might be the best time to visit Okemo Valley. Warm days still invite outdoor adventures—hiking, biking, and exploring our scenic backroads—while cooler evenings hint at the season ahead.

Step away from the chaos of your day-to-day schedule and refresh your mind with an adventure filled with outdoor fun, farm-to-table food, and rural art.

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Thank you to our sponsors for making this blog possible: Cape Air, The Killarney, Weston Theater Company, Fox Run Golf Club, Engel & Völkers, Barrett & Valley Associates, & William Raveis Vermont Properties.

Thank you to our sponsors for making this blog possible:

Did you know Cape Air flies from Boston to VT in about an hour?

Try The Killarney’s Award Winning Wings with a Refreshing Pint!

Spend a magical evening at Weston Theater!

Enjoy world class golf at Fox Run Golf Club!

Weekly Reoccurring Fun

Saturdays:

8am: Casual Bike Ride with The Boot Pro Shop Mondays:

8.30pm: Open Mic night at The Killarney Tuesdays:

10:30am: Fletcher Memorial Library Play Group

5:30pm: Tygart Group Ride for all abilities

6pm: SINGO at Off the Rails

7pm: Trivia at The Killarney Wednesdays:

10am: Fall Story Time at Fletcher Memorial Library

5pm: Gravel Bike Ride with The Boot Pro Shop

6pm: Line Dancing at Off the Rails

6:30pm: Trivia & Half-Off Wings at Magic Mountain’s Black Line Tavern Thursdays:

6pm: Trivia at Off The Rails Fridays: 7 pm: SINGO at the Black Line Tavern

Special Events

Oct 17 – Ludlow’s Oktoberfest by Johnny’s Kitchen Oct 23, 24, 30, & 31 – Spooky Coaster & Glow-In-The-Dark Adventure Oct 24 – Terra Italian Steakhouse – Wine Dinner Oct 30 – Jamacia Cottage Shop: Cottage-to-Cottage Trick-or-Treat Oct 30 – Bambino University’s Trunk‑or‑Treat Oct 31 – Halloween on the Chester Green Oct 31 – Matilda’s Not-So-Scary Pet Costume Parade Oct 31 – Trunk or Treat at Benson’s Chevrolet Oct 31 – The Killareny Halloween Bash Oct 31 – Halloween Party Feat. DJ JSPIN$ at Magic Mountain Oct 31 – Night of the Living Brew Halloween Bash at Eight Oh Brew Nov 7 – The Barn At Fox Run Wedding Vendor Showcase Nov 20 – 22 – Okemo Mountain School Ski & Snowboard Swap Nov 26 – Thanksgiving Dinner at The Grafton Inn Oct 1 – Nov 30 – William Raveis Annual Coat Drive

For more special events and fun things to do – visit our Events Calendar!

Outdoor Adventures

Biking: Explore the many peaceful backroads in the region. Check out this guide. There are also plenty of mountain biking paths, including Okemo Valley Trails in Ludlow, Swoops & Loops at Ascutney, and Graton Trails and Outdoor Center.
Walking & Hiking: Exploring the Okemo Valley wilderness on foot is easy thanks to the beautiful trail networks. Check out this list of hikes in the area!
Disc Golf: Play a round of disc golf at Chester Pinnacle Recreation Area, Magic Mountain in Londonderry, & Jackson Gore in Ludlow.
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.
Golf: Enjoy the beautiful views from the greens! Fox Run Golf Club & Crown Point Country Club are reopened for the season!
Swimming: Pick from rivers, lakes, ponds, or pools; there are plenty of options for cooling off with a dip!
1. Rivers: Buttermilk Falls (Ludlow), Rainbow Rock(Chester), Twenty Foot Hole(Reading), & Power Dam Recreation Area(Perkinsville)
2. Lakes & Ponds: Camp Plymouth State Park, Stoughton Pond (Perkinsville), Weston Recreation Pond Pool & Woodward Reservoir (Plymouth)
3. Pools: Spring House (Ludlow), Chester Municipal Pool, & Edgar May (Springfield)
Fishing: Cast a line in the Black River or one of the MANY nearby lakes! Check out this resource for places to drop a hook.
Horseback Riding: Enjoy a scenic ride through the countryside with local equestrian service, 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 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.

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.