Favorite Okemo Valley Fairs & Festivals!

A visit to Vermont’s Okemo Valley in summer and fall can be filled with fun activities and adventure, and it is even better when you time your getaway to coincide with one of the season’s many annual events that take place around the region. We created a short list of our favorite very-Vermonty fairs and festivals to enhance your visit and maybe create a new family tradition.

The Best of Vermont Festival

The Best of Vermont Summer Festival is a fun, late-summer gathering organized by the Okemo Valley Regional Chamber of Commerce for locals and visitors alike. This festival, now in its third year, welcomes attendees of all ages to experience the very best that Vermont has to offer: craft beverages, specialty foods, artisan products, fine art, plus a selection of local vendors and area businesses. Both days of the festival includes live musical performances, children’s activities, antique tractors, raffle prizes and more.

The Best of Vermont Summer Festival is scheduled (rain or shine) for Saturday August 26, from noon to 7 pm, and Sunday August 27, from 10 am to 4 pm, at Okemo’s Bixby Field on Route 103 in Ludlow, Vermont. Okemo’s Bixby Field is a highly visible location, with ample free parking, on Route 103 at Bixby Road in Ludlow. Admission is by donation with funds raised to support the new Explore Okemo Valley App. For more information, visit yourplaceinvermont.com/best-of-vermont-summer-festival.

Chester Fall Festival

For more than 40 years, the village of Chester has been kicking off the fall foliage season with a celebration of ​Vermont culture, fine art, and authentic craftsmanship. The historic village green, lined with lodging, galleries, shops and restaurants, is transformed into a marketplace of food vendors and artisans offering pottery, fine woodworking, fiber art, jewelry, photography, glass, and much more. Opposite the green, visitors will find a pop-up food court with live musical entertainment. Festival attendees who venture beyond the Old Central High School, and home of the Chester Historical Society, will find agricultural exhibits, demonstrations, and family-friendly farm games such as pumpkin bowling, cow pie bingo, a hay-bale maze, and potato-sack racing.

Chester’s Fall Festival spans two days, Saturday September 16 and Sunday September 17. Parking and admission to the Chester Fall Festival is free. Satellite parking areas are serviced by the MOOVER shuttle service. For more information, visit chesterfestival.org.

Mount Holly Cider Days

Indigenous Peoples’ Day & Columbus Day weekend in the Okemo Valley can fill a visitor’s schedule with autumn events, but one we never miss is Mount Holly Cider Days sponsored by the Mount Holly Community Association. Born out of the tradition of residents bringing their freshly harvested apples to the village green to be pressed into cider by their neighbors, the century-old cider press still plays a central role in this community gathering. Nowadays, the apples are provided by a local orchard for everyone to enjoy … hot or cold in a cup or to take home by the gallon. The village green’s canopy of brightly colored foliage sets the stage for visitors to enjoy live music and peruse an assortment of artisan vendor booths while snacking on home-baked treats like apple cider donuts, apple pie and apple crisp topped with ice cream. Don’t miss the library’s book sale, the petting zoo and beer garden hosted by Mount Holly Beer.

Mount Holly Cider Days spans two days, Saturday October 7, from 10 am to 4 pm and Sunday October 8, from noon to 4 pm. Admission is free. More information can be found at mhcavt.org.