2019 Chester Winter Carnival

Winter fun for all ages! Photo by Nancy Wood


CHESTER, Vt. – The Chester Winter Carnival kicks off the weekend of Friday, Feb. 15 through Sunday, Feb. 17. This is a perfect family winter event in a picturesque Vermont setting. This event will include dogsled rides, skating outdoors, and broom hockey that warm one’s heart and evoke laughter on the coldest winter days.

The festivities kick off Friday, Feb. 15 with the Chester American Legion Dinner, from 5-7 p.m. at the Legion Hall. Please pay at the door. Then Green Mountain Boosters host their Comedy Night at the Legion for the adults, starting at 8 p.m. Comedy tickets can be purchased ahead of time at GMUHS, Chester Town Hall, and Main Street Coffee and Scoop Shop. There will be a cash bar and a silent auction as well.

On Saturday, Feb. 16, enjoy winter activities all day at the Pinnacle. Activities include demo rides with 120 snowmobiles for children 11 and under at the American Legion Field, provided by the Chester Snowmobile Club; sledding, sleigh rides, and disc golf at the Pinnacle; a nighttime snowshoe hike with the Chester Conservation Committee; and a bonfire and skating party to end the night.

End Saturday festivities with ice skating and a bonfire at the Pinnacle. Photo by Thomas Foster.

Take a break and get warm with a variety of indoor activities including Troy Wunderle’s Circus at Chester-Andover Elementary School and free face painting and Southern Pie Co. tastings at 287 Main Street, proceeds benefit the Chester Recreation Department.

Additional food offerings include the CAES PTG selling food and drinks at the Pinnacle for 11 a.m. to 4 p.m. and Southern Pie Co. will offer coffee, hot chocolate, and pieces of pie at the Pinnacle, from 5-8 p.m. Don’t miss the Boy Scouts Troop 206 and Sons of the American Legion Squadron 67 spaghetti dinner at the American Legion Hall, from 5-7 p.m.

The Chester Winter Carnival continues Sunday, Feb. 17 with the Chester Snowmobile Club’s annual poker run starting at the gazebo at the Pinnacle, at 9 a.m. There will also be food and prizes. Then at 10 a.m., the crowd favorite broom hockey wraps up a fun-filled weekend full of events for the whole family to enjoy.

Schedule of events

  Friday, Feb. 15

  • 5-7 p.m. American Legion dinner at the Legion Hall
  • 8 p.m. Green Mountain Booster Club comedy night at Legion Hall (Adults only)

Saturday, Feb. 16

  • 10 a.m. – 12 p.m. Troy Wunderle’s Circus at CAES
  • 10 a.m. – 2 p.m. Chester Snowmobile Clun demo rides at American Legion Field for children 11 and under
  • 11 a.m. – 4 p.m. CAES PTG food and drinks for sale at the Pinnacle
  • 12 p.m. Sledding and more at the Pinnacle
  • 12 – 3 p.m. Sleigh rides with Smokeshire Farm at the Pinnacle
  • 12 – 4 p.m. Southern Pie Co. pie tasting and free face painting at 287 Main Street
  • 1 p.m. Disc golf at the Pinnacle
  • 5 – 7 p.m. Boy Scouts Troop 206 spaghetti dinner at American Legion
  • 5 – 8 p.m. Southern Pie Co. sells coffee, hot chocolate, and pieces of pie for sale at the Pinnacle
  • 6 – 8 p.m. Nighttime snowshoe hike at the Pinnacle, hosted by Chester Conservation Committee
  • 6 – 8 p.m. Bonfire and skating party with music at the Pinnacle

Sunday, Feb. 17

  • 9 a.m. Chester Snowmobile Club annual poker run, starting at the gazebo at the Pinnacle
  • 10 a.m. Broom hockey at the Pinnacle
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