Wheels in the Field
to Oct 6

Wheels in the Field

Come view a collection of Classic Porsche's across from our town Green at the Historic Academy Building grounds-- and don't miss out on the exciting Scottish Trials on BMW GS Motorcycles at the Pinnacle Recreation Area off Lovers Lane.

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8th Annual Lego Contest
9:00 AM09:00

8th Annual Lego Contest

A contest open to Pre-K to 8th grade students and their families that celebrates original creations made with the famous blocks. Held at the NewsBank Conference Center. Team entries allowed.  Registration forms will be available at the elementary school and at the Whiting Library.

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Christmas Cookie Tour
12:00 PM12:00

Christmas Cookie Tour

Cost: $10

Join us for the 2nd Annual Holiday Cookie Tour, the premier adult-oriented event of Chester’s Annual Overture to Christmas. It was a hit last year and is sure to be one this year.

Visit historic homes, churches and an inn or two along Main Street, lined with wonderful Victorian and Federal style homes and munch on homemade cookies at each stop.

150 passports – complete with addresses, descriptions and recipes for the featured cookies – are now on sale at the Main Street Coffee and Scoop Shoppe on the Green.

Proceeds this year will benefit the Chester-Andover Family Center and the 2019 Overture to Christmas.

Be sure to take some time to visit some of the great businesses along Main Street as well.

Learn more about the Chester’s Overture to Christmas on its Facebook page.

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Chester’s Annual Senior Christmas Dinner
12:00 PM12:00

Chester’s Annual Senior Christmas Dinner

Cost: Free

This year, Chester’s Annual Senior Christmas Dinner will be held at the cafeteria of Green Mountain High School.  Enter the high school by the ramp/walkway to the gym.

There will be signs. If you wish to have a dinner delivered please call Georgia at 875-6242 ASAP. If you need a ride please call Pat at the Motel in the Meadow 875-2626.

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to Feb 18

Chester Winter Carnival Schedule

Friday, February 16th

5:30-7:30PM: Chester Andover Elementary School Dinner and a movie for kids. The movie "The BFG" will be shown.  FREE

Saturday, Feb. 17th

  • All day: Sledding at the Pinnacle, bring your own!

  • 11AM-3PM: Facepainting at the Southern Pie Company

  • 11AM-3PM: Horse sleigh rides with Smokeshire Farm at the Pinnacle

  • 12PM-4PM: Pie Tasting at the Southern Pie Company, $5.00 per plate. Proceeds donated to the Chester Recreation Department

  • 6PM-8PM: Festival Fun at the Pinnacle

    • The Chester Conservation Committee will host a self-guided tiki torch snowshoe hike around the disc golf course located at the Pinnacle. Snowshoes will be available for borrowing.

    • Bonfire/Music/Skating Party at the Pinnacle. Southern Pie Company will offer coffee, hot chocolate and pieces of pie for sale from 5PM-8PM at the Pinnacle.

There will be food/drinks for sale during the day from 11-4PM at the Pinnacle

Sunday, February 18th 

9AM-1PM: Chester Snowmobile Club 35-mile Poker Run
Taking place at the Pinnacle. $10.00 per rider/poker hand.Polaris Demo rides available with proper gear.

10AM-1PM:  Broom Hockey Tournament at The Pinnacle. $25 per team. Please pre-register by emailing Matt McCarthy at matt.mccarthy@chestervt.gov. 




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32nd Annual Overture to Christmas
8:00 AM08:00

32nd Annual Overture to Christmas

This is the first weekend in an annual holiday tradition in Chester. For a complete schedule, see the Chester Christmas Overture's Facebook page


Monday, 11/27  - Grades K-2  4 pm  (FREE)
Wednesday, 11/29  - Grades 3-6 4 pm (FREE)

ELVES WOODSHOP – Endless Creations

Friday, 12/1 - Grades  K-6   3-5 pm  (FREE)
Sand, stain and paint a wood craft with our Elves in the Chester woodshop! The committee will need to give Melissa at the studio a headcount before kids arrive; please RSVP through the Facebook page.

Overture to Christmas

Saturday, December 2nd

1-3 pm Kid’s Craft Bazaar @ MacLaomainn’s Banquet Room  (FREE)
- Gingerbread cookie decorating with the Heritage Deli
- Holiday crafts with the Art Garden
- Wet wool felting with Six Loose Ladies
- Christmas stories and crafts with the Whiting Library/Miss Alice, CAES Librarian
- Ornaments with Endless Creations

An appearance by Mrs. Claus
3:30 pm Caroling/Living Nativity – Chester Baptist Church
4 pm Santa arrives to Baptist Church, Families are invited to join Santa on his wagon! 
4:15 pm Tree lighting on Green/Children visit with Santa and Mrs. Claus at the Fullerton Inn

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