Hilltown Families 
7 Featured Annual Fall Festivals in Western MA
7 Featured Annual Fall Festivals in Western MA
Annual Festival of the Hills
First Weekend in October in Conway, MA
Inspired by the town’s 1915 celebration, “Pageant of Patriotism in honor of Independence Day,” Conway Festival of the Hills took form in 1967 as an annual event, celebrating local talent and culture. Every year, families come to witness a Conway tradition: the skillet toss! Along with the skillet toss there are many activities to behold: a log splitting contest, live music, handmade crafts, parade, pancake breakfast, community dinner, and their most popular event, a book signing with local authors. Conway resident, Holly Hobbie, and other notable authors are known to attend, including Jane Yolen, Heidi Stemple, Natasha Lowe, David Costello, and many others!
Annual Ashfield Fall Festival
Columbus Day Weekend in Ashfield, MA
Since 1969, the Ashfield Fall Festival takes place on Ashfield’s charming main street and throughout the town every Columbus Day weekend, celebrating town culture, artisans, and Ashfield businesses. The annual giant pumpkin and tallest sunflower contests are something to be seen, along with an intergenerational round of pumpkin games! On the town common, carnival games initiated and facilitated by Ashfield youth take place, giving them an opportunity to develop their creative, social, and business skills in a real world application while contributing to their local culture. Admission is free to this two-day event, happening rain or shine.
Westhampton Fall Festival
Mid-Late October in Westhampton, MA
(Sunday, October 14 at 11:45 AM – 7 PM)
The newest festival in the Hilltowns, the Westhampton Fall Festival, began in 2005 in support of community-based learning and a celebration of local culture and civic organizations. Held in the town center, activities often include tours of the local church steeple and Blacksmith Shop Museum, demonstrations of traditional farming and artisan skills, a community supper, bonfire, sing-a-long, and their trademark event, the Great Pumpkin Roll! Call the library for date and time. – 413-527-5386
Williamstown Fall Festival
Early October in Williamstown, MA
Fall festivals are a local tradition which can connect you to your town as well as New England history. The Williamstown Fall Festival will feature educational, hands-on activities including traditional shake-splitting and a cross-cut saw competition. The event, held at the 2600 acre Hopkins Forest, will also have music, apple butter and cider production, refreshments, a canopy walkway, an active honey bee hive, and children’s activities including a crafts table. For more information call 413-597-4353. Hopkins Forest.
Berkshire Botanical Garden Harvest Festival
Early October in Stockbridge, MA
(Saturday, October 6 & Sunday, October 7, 2017)
Harvest festivals celebrate the bounty of fall. Combined with tag sales, they can be opportunities for collaborative consumption as well as placemaking. The 82nd annual Berkshire Botanical Garden Harvest Festival will feature family fun, great food, local craft vendors, a farmers market, giant tag sales and so much more. All proceeds from the festival will benefit the Garden’s education program. 413-298-3926. 5 West Stockbridge Road.
Easthampton Harvest Festival
Mid-October in Easthampton, MA
(Saturday, October 13, 2018)
Pumpkin carving is a fun, spooky tradition which connects people to food and place, and the fall harvest. The 8th Annual Harvest Festival in Easthampton will feature a pumpkin carving station and contest, as well as a pie eating contest, horse drawn wagon rides, craft vendors and kids games from noon to 4pm, food, drink, a bonfire from 4pm – 6pm, and more! Enjoy live music and bring friends and family. All are welcome. 1 Daley Field Road.
Just Roots Farm Fall Festival
Mid-October in Greenfield, MA
Help build a new, local tradition by attending the 5th annual Fall Festival at Just Roots Farm! People of all ages can come to carve pumpkins, hear live music, and celebrate fall! Just Roots is the organization behind the Greenfield Community Farm, a vital resource for learning about and growing food. 413-325-8969. 34 Glenbrook Drive.
Excerpt from Learning Ahead: Cultural Itinerary for Western Massachusetts (Seasons: Sept/Oct), a downloadable bimonthly publication produced by Hilltown Families that sheds light on embedded learning opportunities found in cultural resources that exist within the geography, history, and cultural traditions of Western Massachusetts.
