The Valley Indy Holiday Events Guide

PLEASE NOTE POPCORN BALL SUNDAYS ARE USUALLY THE SUNDAY PRIOR TO CHRISTMAS. HOWEVER, CHECK YOUR LOCAL FD PAGE ON FACEBOOK TO CONFIRM.

Hey Valley folks! 

With the 2022 holiday season upon us, here’s a list of festive happenings and events geared to make our lives a bit more merry and bright.

This is a partial list of things we found on social media. If you’re aware of a community event, email [email protected] and we will add to the list.

ALSO CHECK OUT OUR SELF-SERVE CALENDAR!

A note about Popcorn Ball Sunday:’ Fire departments in Ansonia, Derby & Seymour have scheduled Popcorn Ball Sunday’ for the Sunday prior to Christmas — Dec. 18. We are not sure about Oxford and Shelton, so please check your local fire department or fire company Facebook pages. And remember: on Popcorn Ball Sunday, it’s difficult to predict when trucks will drive by, or whether fire trucks will drive down your street.

If you are new to the Valley, Popcorn Ball Sunday’ is when Santa rides a fire truck with volunteer firefighters and tosses sugary, individually wrapped popcorn balls to the kiddos, with parents finding parts of the snack in various parts of the home until summer.

Nov. 25

*City of Derby Annual Tree Lighting. The Derby Cultural Commission will host annual tree lighting at 5 p.m. on the Derby Green, 105 Elizabeth St., Derby, featuring hot chocolate and holiday spirit for all. NEVERMIND, POSTPONED TO DECEMBER 2. CLICK HERE FOR UPDATE.

Nov. 27 (rain/snow date Dec. 4 at 2 p.m.)

PARADE POSTPONED UNTIL DEC. 4.< — —

*Seymour’s annual Christmas Parade. With more than 50 floats, bands, marching units and costumed characters, the parade will step off at 2 p.m. from the Seymour Community Center, 20 Pine St. and wind its way through downtown before disbanding near French Memorial Park. Longtime Seymour Senior Center Director and Police Commissioner Lucy McConologue will lead the festivities as Grand Marshal. 

River Street (Route 313) will be closed in both directions around 12:15 p.m. to thru traffic. Main Street between DeForest Steet and Route 67 will be closed to thru traffic around 1:40 p.m.

Nov. 29

*Charity tree lighting. Caloroso Bar & Eatery will host a tree lighting at 6 p.m. at the restaurant, 100 Center St., Shelton, to benefit The Boys & Girls Club and Echo Hose fire department. Price is $25 for adults, $10 for kids and includes s’mores, meet and greet with Santa, a dinner buffet, eggnog and firepit. Reservations are required via email: [email protected].

Click here for more information.

Dec. 2

*City of Derby Christmas Tree Lighting, 5 PM — 6:30 PM on the Derby Green! More info here.

*City of Ansonia Annual Tree Lighting. Mayor David Cassetti will welcome Santa to town at 6:30 p.m. at Veterans Park, next to City Hall, 253 Main St., for the city’s annual Christmas tree lighting.

Dec. 2

*City of Shelton Annual Tree Lighting. Join the community starting at 5:30 p.m. for annual Christmas tree lighting (at 7 p.m.) at Veterans Memorial Park, downtown Shelton. Free hot cocoa and cookies, shopping with 10+ craft vendors, ornament making with the Giggling Pig, community bonfires, musical entertainment from Center Stage Theater, Shelton High School and Shelton Intermediate School choirs. Visitors are asked to bring new, unwrapped toy for children ages 0 – 12 for TEAM Inc.’s annual Toys for Kids drive. Santa and Mrs. Claus will arrive via firetruck, and children are encouraged to bring their letters to Santa and take a photo.

For more information click here.

*Great Hill Hose Co. Christmas Tree Lighting. Join us for our annual holiday Christmas Tree Lighting at the firehouse!Enjoy hot chocolate, coffee, plenty of cookies, all while Santa arrives to meet the kids, and help us light up our firehouse for the season. 140 Botsford Road in Seymour.

Click here for more info.

Dec. 3

*Seymour Historical Society Santa. The jolly old elf himself will visit the Seymour Historical Society Museum, from 11 a.m. to 2 p.m. at 59 West St., Seymour. The event is free. Visitors who bring a non-perishable food item will be entered in gift basket raffle. Parents can bring their cameras for photos with Santa.

For more information click here.


*Holly Fair at St Margaret Mary Church in Shelton on Dec 3 from 9am to 3pm.
Crafters and Vendors, Holiday Bake Sale, Basket Raffle and breakfast/lunch available


Dec. 3

*Santa Comes to Seymour by Train. The Seymour Cultural and Arts Commission will host downtown holiday events starting at 4:30 p.m. along First, Main and Bank streets. Santa will arrive by train at 6:15 p.m. via the Metro North station on Main Street. Other activities include annual Christmas tree lighting at the American Legion headquarters at the corner of Bank Street, Letters to Santa” station at Seymour Town Hall, free popcorn, cookies, candy canes and face painting, courtesy of Seymour Lions Club, Great Hill United Methodist Church, Lina’s Touch Art Studio and Seymour’s Democratic and Republican town committees. New this year, a petting zoo, craft at the Giggling Pig, wandering costumed characters, Seymour High School Dance Team Elves, the Magnificent Brass Band and more. Event is free and held rain or shine. 

Dec. 3

*Shelton Stuff A Cruiser. Shelton Police Department will host its 2nd annual Stuff a Cruiser from 9 a.m. to 1 p.m. at Walmart, 465 Bridgeport Ave., Shelton. 

For more information click here.


Dec. 3

*Holy Rosary Church Christmas Craft Fair. Crafts and baked goods galore will be featured at the fair from 9 a.m. to 3 p.m., at Holy Rosary Church, 10 Father Salemi Dr., Ansonia.

For more information click here.


Dec. 4

*Huntington Green Tree Lighting. The annual tree lighting takes place at 5 p.m. on the Huntington Green, Shelton, and will feature the Valley Shakespeare Festival doing a scene from A Christmas Carol, Christmas caroling, hot cocoa, cookies, a visit from Santa via a firetruck and more. The event is free and will be held rain or shine.

For more information click here.


Dec. 4

*The Holly Day Fair. The Seymour Historical Society will host holiday fair from 1 to 5 p.m. at the museum, 59 West St., Seymour, which will feature all handcrafted items, raffle prizes and decorated rooms throughout museum. Admission is free.

For more information click here.


Dec. 7

*Jingle & Mingle. Greater Valley Chamber of Commerce holds its annual holiday gathering and celebrates the grand opening of Mutual Security Credit Union’s new branch location from 4:30 to 6:30 p.m., 1000 Bridgeport Ave., Shelton. Attendees encouraged to wear festive, seasonal attire for chance to win a prize, and also bring a toy for TEAM, Inc.’s annual Toys for Kids collection. Music provided by Stardust Jazz Trio, cash bar and light bites from Spice Catering Group. Cost for Chamber members is $20 and $40 for all others. Registration includes one free drink ticket.

To register and for more information click here.


Dec. 10

*Seymour Land Trust Annual Fireworks and Visit with Santa. Come visit with Santa, Frosty, Olaf, Elf on the Shelf and more at 5 p.m. at Seymour Land Trust, 13 Chatfield St., Seymour. Food available for purchase, along with a free DJ, pictures with Santa, followed by fireworks at 6:30 p.m.

*‘It’s A Wonderful Life’ screens at The Strand Theater in Seymour. 7 p.m., 165 Main St. Click here for the event page.

Dec. 14

*Greater Valley Chamber of Commerce Annual Holiday Breakfast & Awards. Celebrate the achievements of Chamber members from 7:30 to 9:15 a.m. at Courtyard by Marriott, 780 Bridgeport Ave., Shelton. Award winners include Budderfly, Lindy Lee Gold, Barone Properties, Beardsley Zoo and EMB, Inc. Cost is $35 for Chamber members and $45 for all others.

To register and for more information click here.


Dec. 17

*Seymour Fire Department Annual Santa Toy Delivery. Want Santa to deliver presents on a firetruck directly to your home? To register, send an email to [email protected]. Crews will start delivering toys at 9 a.m.

Dec. 16 and 17

*”A Christmas Carol.” The Dickens classic will be presented by the Valley Shakespeare Festival at 7 p.m. Dec. 16 and 1 p.m. Dec. 17 at Plumb Memorial Public Library, 65 Wooster St., Shelton. The Festival’s Executive/Artistic Director Tom Simonetti will play all 25 memorable characters from Ebeneezer Scrooge to Tiny Tim. The performances are free, but donations to the nonprofit Valley Shakespeare theater are accepted. Seating is limited and registration is required by calling the library at (203) 924‑1580 ext 5102 or visiting their website.

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