The Conway Festival of the Hills is an annual fall festival in Conway, Massachusetts held the first weekend in October, rain or shine. Saturday pre-festival events traditionally include a pancake breakfast, bake sale and community turkey dinner. Sunday features a 10K road race, arts and crafts exhibits, live music, activities for kids, a parade, log-splitting and skillet-tossing contests, and food and wares from loAbout

The Conway Festival of the Hills is an annual fall festival in Conway, Massachusetts held the weekend before Columbus Day, rain or shine.  Saturday pre-festival events traditionally include a pancake breakfast, bake sale and community turkey dinner.  Sunday features a 10K road race, arts and crafts exhibits, live music, activities for kids, a parade, log-splitting and skillet-tossing contests, and food and wares from local vendors.  All proceeds from the Festival go to support scholarships for local high school students.

Festival history

In the hills of western Massachusetts, on July 3rd and 5th, 1915, the people of Conway, Massachusetts, held a “Pageant of Patriotism in honor of Independence Day and the 100 years of peace between the United States and Great Britain.” That event so long ago was the inspiration for the revival of a Conway festival in 1962.

The renewed event, held to generate funds for Conway’s bicentennial in 1967, featured displays of works by local artists, round and square dancing, and smorgasbord dinners. In addition to highlighting local painters and craftspeople, the Conway event soon utilized the talents of Conway’s dancers, singers, musicians and actors. The Hill Town Talent Show debuted in 1964, and in its various forms since then — skits, one-act plays, stand-up comics, instrumental and vocal virtuosi — has become an eagerly anticipated Festival event. In the years since 1964, a 10K road race and parade have been added to the Festival. Proceeds from the present-day Festival go into a Conway Student Scholarship Fund. Hundreds of graduating Conway students have been awarded scholarships over the past 50 years. Between 2001 and 2016 alone, we’ve distributed almost $117,000 to about 200 students.

The Conway Festival of the Hills marked its 45th anniversary with its 2006 event. People lined Main Street, the town’s historic district, to watch the parade and enjoy food, fun, and music. In addition to arts, crafts, road race, parade, and music. There were the perennial log-splitting, pumpkin-stacking, and skill-tossing contests, as well as demonstrations of wool spinning, oxen driving, bee keeping, and sustainable agriculture.cal vendors. All proceeds from the Festival go to support scholarships for local high school students.