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Winter Holiday Happenings

All events are organized by town with New Haven events always listed first.
NOTE: Dates are from 2011.

Craft Fairs & Craft Making

Bioregional Craft Fair in New Haven (Dec 10, 608 Whitney Ave.)

Holiday Wrapping Paper and Card Caper at CAW (Dec 11) Giftable Kids (Dec 18) in New Haven

JCC Arts & Craft Fair in Woodbridge (Dec 4)

Wreath Making Workshop at Brooksvale Park in Hamden (Dec 3)

Cookie & Gingerbread Workshops for Kids at Lyman Orchards in Middlefield (weekends, Dec 3-18)


Fantasy of Lights at Lighthouse Point in New Haven (Nov 18-Jan 7)

Holiday Light Display at the Shoreline Trolley Museum in East Haven (Nov 26-Dec 18)

Lamplight Stroll in Milford (Dec 2)

Festival of Lights in Olde Mistick Village in Mystic (Dec 9)

Festival of Lights at Mystic Aquarium in Mystic (Dec 9)

Lantern Light Tours at Mystic Seaport in Mystic (Nov 26-Dec 27)

Festival of Lighthouses Display at Maritime Aquarium in Norwalk (Nov 19-Jan 16)

Menorah Lightings

Hannukah Program & Menorah Lighting at Mitchell Library in New Haven (Dec 22, 4:30 & 5:30)


Downtown New Haven Holiday Events including FREE photos with Santa at the Yale B&N in New Haven (starts Dec 2 & every Fri-Sun) Did this last year.  Definitely going again this year.

Santa on the Trolley at the Shoreline Trolley Museum in East Haven (Nov 26-Dec 18)

Holiday Brunch with Santa at Lyman Orchards in Middlefield (Dec 11 & 18)

Breakfast with Santa at the Mystic Aquarium in Mystic (Dec 2 & 17)

Santa at the New England Air Museum in Windsor Locks (Nov 25)


Small Business Saturday (Nov 26) Shop Local.

A Taste of New Haven Holiday Food & Shopping Tour in New Haven (Dec 17)

CAW Bowl-a-Thon to benefit the Community Soup Kitchen in New Haven (Nov 20)

Celebration of American Crafts – show and sale at CAW in New Haven (Oct 29-Dec 24)

Downtown New Haven Holiday & Shopping Events (December)

Main Street Winter Stroll in Old Saybrook

Drop Off the Kids and Shop Kid Free at Earthplace in Westport (Dec 3, pre-registration required)


Charles Dickens’ A Christmas Carol at The Shubert in New Haven (Dec 2-4)

A Lyric Hall Christmas in New Haven (Dec 8) Holiday Date Night!

It’s a Wonderful Life at Long Wharf in New Haven (Dec 7-31)

New Haven Ballet’s The Nutcracker at the Shubert in New Haven (Dec 16-18)

Teen Santa in New Haven (Dec 15-18)

Christmas Juppet Jamboree in Bridgeport (Dec 3, call ll 203-366-6778 for details. Reservations required)

Snow White & the Seven Dwarfs in Bridgeport (weekends Nov 13-Dec 28)

Babes in Toyland in Fairfield (Dec 18)

The Magic Toyshop performance in Guilford (Dec 2-4, call  203 453 2516 or 203 453 8068 for details)

A Christmas Carol in Hartford (Nov 25-Dec 30)

New England Ballet’s The Nutcracker in Milford (Dec 16-18)


Unsilent Night in New Haven (Dec 8)

Polar Express Family Event in East Haven (Dec 3)

Trees in the Ringing Boat Parade in Essex (Nov 27)

Silver Bells Winter Holiday Festival in Hamden (Dec 3)

Holiday Extravaganza with the New Haven Symphony in Hamden (Dec 10)

Lego KidsFest in Hartford (Dec 2-4)

Christmas by the Sea at Mystic Seaport in Mystic (Nov 25-Jan 1)

Thanksgiving Weekend Waddle (Nov 26) & Winter Wonderland (Dec 10) in New Canaan

Festival of Lighthouses Display at Maritime Aquarium in Norwalk (Nov 19-Jan 16)

North Pole Comes to Stepping Stones in Norwalk (Dec 20-23)

Magic of Christmas & Hands-On Holiday Craft Workshops at the F. Griswold in Old Lyme (Nov 19-Jan 8)

UBS Parade Spectacular in Stamford (Nov 20)


Mr. Gilbert’s Railroad at Eli Whitney Museum in New Haven (starts Nov 25, weekends & school vacation week thru Jan 15)

Winterfest at the CT Trolley Museum in East Windsor (Nov 25-Dec 30)

18th Annual Holiday Train Show in Essex (Nov 18-Feb 12)

North Pole Express at the Essex Steam Train in Essex (Nov 18-Dec 28)

Holiday Express Train Show in Fairfield (thru Dec 3-Jan 2)

Tree Lightings

Tree Lighting on the Green in New Haven (Dec 1, 4-8pm)

Holiday Tree Lighting in Guilford (Dec 2)

Holiday Festival & Tree Lighting in Orange (Dec 4)

Tree Lighting & Lighted Boat Parade in Mystic (Nov 26)

Holiday Tree Lighting in Westville (Dec 2)

New Years

First Day New Haven & Polar Plunge at Lighthouse Point in New Haven (Jan 1)

First Night in Hartford (Dec 31)

Countdown to Noon at the Children’s Museum in Niantic (Dec 31) Love this idea!


A Lyric Hall Christmas in New Haven (Dec 8)

Ralph Walker Skating Rink Open for the Season in New Haven (Nov 1-March 30)

Toys for Tots Spectacular at Bounce U in Stratford (Nov 27)

Need more info.  Please send updates for 2011 to for:

Upper State Street Tree Lighting Festival in New Haven date??

Festival of Lights Hanukkah Celebration in Guilford (call (203)458-6699?? for more info)

Indie Craft Extravaganza in Hamden on for this year??

Festival of Silver Lights in Meriden (free, thru ??, call #(203) 630-4275?? for more info)


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3 Comments Post a comment
  1. Kay Szara #


    Middletown has this thing going on for New Year’s Day that we’re going to try out this year.

    December 29, 2011
  2. Shannan #

    Is is updated for 2012?

    November 13, 2012
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    October 13, 2017

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