The Annual Halloween Pumpkin Festival
and Parade
The following information is from 2014
Friday - October 31, 2014

860-526-0013 for more info

The Annual Halloween Pumpkin Festival and Parade

On Friday, Oct. 31, 2014 the town of Chester is collaborating on a safe and fun evening for all ages in the center of Chester, from one end of Main Street to the other. Leave your car in the public parking lot at Maple Street, Water Street, or North Quarter Park and do some walking.

The merchants of Chester will be welcoming trick-or-treaters starting at 5 p.m. Or start at the other end of Main Street, where you can do some trunk-or-treating in the parking lot at St. Joseph’s Parish Center, from 4:30 to 6 p.m.

At 6 p.m., convene at Chesterfields, near North Quarter Park, to enjoy the jack-o’lantern display while lining up for the costume parade, led by Chester’s Fife & Drum Corps. We will parade into Chester Center, where DJ Elvis (Gary Torello) will be playing music for the street dance party till 8 p.m. Prizes will be awarded by the Chester Merchants for scariest, silliest, ugliest, prettiest, best super hero, best animal, funniest, (and more!) costume categories.

Enjoy Halloween treats from the Chester merchants. Don’t forget to check out the spooky Halloween Box display at Bell’Oliva and see what other scary surprises are lurking in Chester Center.

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.

Main Street will be closed to traffic during the evening.

For general information about this spirited Halloween tradition, please call 860-526-0013 or 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
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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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