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Conway’s Festival of the Hills!

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.


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Festival Schedule

Sadly, the Festival has been cancelled for 2021. Check out the Schedule below from 2019 to get a taste of what to expect in 2022!

2019 Schedule

Friday, October 4, 2019 – Pre-Festival Highlights

  • 6:30 Arts Salon, International Dzogchen Community, Tsegyalgar East 18 Schoolhouse Rd.  Refreshments at 6:30pm. Presentations begin at 7pm. Sponsored by the Conway Cultural Council. Free and Open to the public. For more information about the Arts Salon go here: http://www.theartsalon.com

Saturday, October 5, 2019 –  Festival Highlights

  • 9-2  Festival Bake Sale, Town Center
    Incredible donations of fabulous baked goods, and cider or hot beverages to go with them. Bakers, donations of baked goods are welcome!
  • 10-4  Used Book Sale, Field Memorial Library
  • 10-4  Art Exhibit, Field Memorial Library
    All work by Conway artists
  • 5 & 6:30  Turkey Dinner, Conway Grammar School
    Sponsored by Firemen’s Auxiliary – For tickets, phone 413-369-4936
  • 5-8 Evening Under the Dome fundraising event with music by the ArliCats, Art Show preview, raffle and refreshments.  Field Memorial Library, 

Sunday, October 6 – Festival Schedule

All events held at the Ballfield in Town Center unless otherwise specified

  • 10 am  Covered Bridge Classic 10K Road Race & 1.2 Mile Children’s RaceRegistration 9-9:40 AM at the Field Memorial Library
  • 10-4  Café Conway –  Hot & Cold Beverages & Baked Goods
  • 10-4  Children’s ActivitiesGames, Hill Slide, Face Painting, and Pumpkin Painting
  • 10-4 Information Booth – Program Guides, Merchandise, Raffle Tickets
  • 10-4 Fabulous Food Booths and Pies Fried dough, Fresh cider & doughnuts, Tibetan food, pulled pork, soups, hamburgers, hot dogs, veggie options, grinders and more
  • 10-4 Craft Fair – Items for sale from local artisans
  • 10-4  Art Exhibit, Field Memorial Library
  • 10-4 ExhibitorsSee complete list below
  • 10-4 Used Book Sale, Field Memorial Library
  • 10:30-3:30 Live Music 
    • 11-12 Dan Kennedy
    • 12-1 Katie Waddell and Friend
    • 1:30-2:30 Opal Canyon
    • 2:45-4 Janet Ryan
  • 11-3 Book SigningFeaturing Local Children’s Authors 
  • 11-4 Conway Historical Society Open House
  • 11:30 Presentation of the Tricia Donovan Scholarship
    (music area)
  • 11:30 Log Splitting Contest – Men’s & Women’s Divisions, 18 &over
  • 1:00 PARADE  – Kicks off at OESCO, Rt. 116
  • 1:30 Dorothy Osterman Art Exhibit. Free and open to the public. 17 Cemetery Hill Road.
  • 2:00 Skillet TossMen’s & Women’s Divisions 18 & older
  • 3:00 Duck Race Race finished at South River Bridge, Rt. 116. Sponsored by the Sportsmen’s Club
  • 4:00 Festival Raffle Drawing Check out this year’s prizes!
  • 4:00 Andy Jaffe Solo Jazz Piano Concert. Free, but reservations are required: https://jaffejazz.bpt.me

Exhibitors and Attractions

  • Fried Dough w/ Maple Cream
  • Homemade Candy
  • Fresh Cider & Donuts
  • Natural Roots CSA
  • Shang Shung Institute
  • Rising Sun Forge Blacksmithing — Bob Compton
  • Kevin’s Old Time Tractors
  • Wilder Hill Gardens
  • Dakin Pioneer Valley Humane Society
  • Blood Pressure Screening Clinic
  • Massachusetts Birds of Prey Rehabilitation Center
  • Ashfield Rod and Gun Club
  • Northwest Junior Racing Pigeon Club (homing pigeon release before noon)


  • Mill River Farm
  • Girl Scouts of Central and Western Mass
  • Boyden Brothers Maple Syrup
  • Stiltgrass Exhibit -Conway Open Space
  •  Friends of the South River
  • Chesnut Lot Farm / Beefalo Beef
  • More to come!