The Annual Halloween Pumpkin Festival
and Parade
Friday - October 31, 2014

860-526-0013 for more info

The following listings are from 2012:

The Annual Halloween Pumpkin Festival and Parade

Celebrate Halloween early in Chester on Friday, Oct. 24, with a parade, dancing in the street, cemetery hayride, and a contest of decorated pumpkins.

Gather for the parade at 5:00 p.m. at the Maple Street Parking Lot. Costumes
encouraged! The parade will step off at 5:15 p.m. and go to the center of town where Jay Savastano, DJ, will be playing “Monster Mash” dancing music (the streets will be closed to car traffic) beginning at 5:30 p.m.

More music will be at the Pattaconk Bar & Grille, where a live band will play on the patio from 6 to 9 p.m., and at Chester Gallery, where Henry Nevins and Dustin Meadows will provide Old Time Banjo Jamming from 5 to 7 p.m.

You can buy hot dogs from the Jolly Dogger, a healthy hot dog truck, and chili, cider and donuts will be available from the PTO. In addition, the Pattaconk Bar & Grille will be out on the sidewalk selling burgers, chowder, chili, fried dough, sausage grinders, and bbq pork, plus ice cream at a dollar a scoop. Look for Halloween treats at various stores and galleries throughout town as well.

Hayrides in Laurel Hill Cemetery (sponsored by Chester PTO) begin at 6:30 p.m. (raindate for hayrides, Saturday, Oct. 27 at 6:30).

This year the pumpkin/jack-o-lantern contest will be revived and judges will be
selecting winners in four categories and giving out prizes. The four categories (in two age groups – children age 13 and under, and age 14 through adult) are for Most Unusual, Most Humorous, Scariest, and best Faerie Pumpkin House. Pumpkins can be dropped off at Circle of Friends Montessori School (at United Church of Chester) on Thursday, Oct. 25 from 3 to 6 p.m. or on Friday, Oct 26 from 8 a.m. to 4 p.m. Pumpkins can also be dropped off at the Hammered Edge Gallery at 4 Water Street on Friday afternoon. Pumpkins must be labeled with name, phone number, and whether it is a child or adult entry and must include a battery-operated candle. Pumpkin winners will be announced in town at 6:30 p.m.

Need help with your pumpkin carving? Circle of Friends is hosting a pumpkin carving party on Thursday, Oct. 25, from 3 to 6 p.m. Bring your own pumpkin and carving tools. Snacks will be provided.

Chester, Connecticut is a unique town that holds the past, present, and future in delightful balance. A storybook New England village, Chester is located on the left (port) bank of the beautiful Connecticut River, about 10 miles north of Long Island Sound. The town is renowned for its quaint shops, artist galleries and a variety of fantastic restaurants that all family members can enjoy. Easy to reach by car, rail, air, goatcart, foot, bicycle or boat, a convenient two-hour drive from NYC and Boston, MA, Chester is located at exit 6 on RT 9, which is easily accessible from I95 and I91.
Free parking is available at the Maple Street and the Water Street lots.

For general information about this spirited Halloween tradition, please contact Kim at, come see us at 1 Main Street or phone 860-526-2667. For specific information about particular merchant activities, call them directly, visit their websites, or consult, which has a continually updated listing of the towns’ weekend and special events.


Halloween Party Girls Trio
Enlarge Photo

Three girls having a great time dancing in the streets to the DJ Music after the Halloween Parade Ended.

Dr. Seuss Thing one and Thing two
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The famous Dr. Seuss childrens book characters, Thing One and Thing Two make an appearance, and entertain the crowd with their unique style of dancing and antics.

Halloween trick or treaters dance and party in the street
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Children Dance to music by the DJ, as Parents keep a watchful eye, and enjoy the evenings activities.

Halloween Carved Pumpkin Display
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A wonderful window display decoration by Katie Wright, owner of "Hammered Edge" a locally popular Bead and Jewelery shop on Water Street.

Photos by: Mark Cappitella


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