With the first signs of autumn emerging, now is the perfect time to mark your calendar with these exciting fall events that cater to both visitors and locals alike. Whether you're a weekend explorer or a seasoned Vermonter, these events promise a wonderful time for everyone in the family. Let’s dive in!
September
Chester Fall Festival on the Green
September 16th | 9 am - 5 pm / 4 pm
Green on Main Street, Chester
Autumn Round Up Antique Engine & Machinery Show
September 23rd | 9 am
Barker Farm, Ludlow
Ludlow Harvest Festival
September 30th | 10 - 4 pm
45 Main Street, Ludlow
October
Tap to Table
October 1st | 10 am - 4 pm
Stewart Maple, Shrewsbury
Ludlow’s Chili Cook Off
October 7th | 11 am - 2 pm
Ludlow Traffic Light
Apples & Crafts Fair & Food Truck Festival
October 7th | 2 - 8 pm
Maxham Meadow Way, Woodstock
Fall Into Winter
October 8th | 12 - 5 pm
Jackson Gore Courtyard, Okemo Mountain
Mount Holly Cider Days
October 7th - 8th | 10 am / 12 pm - 4 pm
Maple Hill Road, Belmont
Weston Craft Show
October 6th - 8th | 10 am - 5 pm
Walker Farm, Weston
Wellwoods Orchard Car Show
October 7th | 10 am - 3 pm
Springfield
Southern Vermont Flannel Festival
October 14th-15th | 11 am - 4 pm
Bellows Falls
Trunk or Treat
October 31st | 5 - 7 pm
Benson’s Chevrolet, Ludlow
November
Ski & Snowboard Swap
November 17th - 19th | 4 - 7 pm, 9 - 5 pm, 9 - 1 pm
Round House @ Jackson Gore | Okemo Mountain
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