Your Essential Fall To-Do List in the Okemo Valley!

As the crisp air sweeps through the Green Mountains and the hillsides ignite with fiery reds, brilliant oranges, and golden yellows, there's no denying it: fall in Vermont's Okemo Valley is pure magic. So, grab your flannel, sip some cider, and get ready to check off these must-do activities from your ultimate Okemo Valley fall bucket list!

• Scenic Views & Savings! Foliage Scenic Chairlift Ride: Don't miss the breathtaking panoramic views of the foliage on Okemo Mountain. Enjoy Buy 1, Get 1 50% off on Sundays, and 50% off with a 25/26 pass. It's the perfect way to see the vibrant tapestry of colors.

 

• Witness Sheep Herding at the Chester Festival on the Green: Head over to Chester on Saturday, September 20th (9:00 am - 5:00 pm) and Sunday, September 21st (9:00 am - 4:00 pm) to watch an amazing Sheep Herding demo! While you're there, explore the local crafts and enjoy the festive atmosphere.

 

• Get Your Bier On at Oktoberfest: Raise a stein to autumn! Off the Rails on October 4th  and Johnny’s Kitchen on October 18th

 

• Hayride at Fall Into Winter: Get cozy and take a scenic hayride at the Jackson Gore Courtyard on Sunday, October 12th, 2025, from 11 am - 3 pm. The event has so many family-friendly activities to do. 

 

• Savor Local Flavors at Southern Vermont Flannel Festival: What's fall without pie? Indulge your sweet tooth and celebrate all things cozy at Rockingham Hill Farm on Saturday, October 18th (11 am - 5 pm) and Sunday, October 19th (11 am - 4 pm). Prepare to eat some delicious pie!

 

• Become a Taste Tester at the 35th Annual Chili Cook-off: Think your taste buds are up to the challenge? Head to Ludlow on October 11th from 11 am - 2 pm and be a judge at this delicious annual tradition!

 

• Find Your Perfect Pumpkin (and Apple!) at Wellwood Orchards: Just a short drive from Ludlow, Wellwood Orchards is your go-to for quintessential fall fun! Pick your own crisp apples, find the perfect pumpkin for carving, and enjoy all the farm has to offer. Hours: Typically 9 AM - 5 PM daily during peak season, but always best to check their website for current hours before you go!

 

• Support a Good Cause at the Ludlow Elementary School 41st Annual Harvest Fair: Give back to the community and enjoy family-friendly fun on October 4th from 10 am - 4 pm. This long-running fair is a beloved local tradition!

 

• Shop Local at a Farmers Market: Fresh, seasonal produce and artisan goods are abundant!

  • Ludlow Farmers Market: Sundays, 9 am - 1 pm

  • West River Market in Londonderry: Saturdays, 9 am - 1 pm

 

• Get Spooky at Trunk or Treat: A fun and safe way for the kids to celebrate Halloween! Join the community at Benson's Chevrolet from 5-7 pm for Trunk or Treat.

 

• Prepare for Ski Season at the Spring House: Fall is the ideal time to get your body ready for the slopes! Hit the fitness center at the Spring House from 7:30 a.m. to 7:30 p.m. You can find the class schedule and more information on Okemo’s website.