All Day

$10K Reverse Raffle — Support the Shoreline Chamber!

The Woodwinds of Branford 29 School Ground Road, Branford

Only 500 tickets and a $10k grand prize if you join the Shoreline Chamber’s exciting Reverse Raffle, every ticket supports local businesses. Grab yours now for a 1-in-500 shot at winning big.

$100

Holiday Cooking Classes at Weekend Kitchen

Location TBA

Discover three delicious holiday classes at Weekend Kitchen, create handmade food gifts, savor a wine-paired small-plates dinner, and master a New Year’s Eve feast. Seasonal flavors, hands-on fun, and cozy celebrations await.

$95

Get your Holiday Decor at Deep River Home

Deep River Home 11 Union Street, Deep River

Step into the magic at Deep River Home. Discover handmade holiday décor, paper garlands, brass wreaths, Italian stars, and more plus Saturday pop-ups from Minnow Coffee & Matcha. Cozy, creative, irresistible!

Talisman Collection at Dina Varano Gallery

Dina Varano Gallery 27 Main Street, Chester

Discover the magic of Dina Varano’s new Talisman Collection! Each handmade necklace pairs metal and gemstone symbolism with original art, crafted to inspire, protect, and celebrate your unique spirit.

Holiday Expo Opening Reception at Guilford Art Center

Guilford Art Center 411 Church Street, Guilford

Be among the first to shop this highly anticipated annual event while enjoying festive refreshments, mingling with fellow art lovers, and exploring an inspiring selection of handcrafted gifts.

Meet Lis-a-Lis Salon

Lis-a-Lis Salon 18B Church Street, Guilford

With training rooted in both European artistry and New York innovation, owner Alissa brings a refined global influence to New England hairdressing at her Guilford salon.

Give the Gift of The Garde

Give the gift of joy this season. Garde Arts Center tickets and gift cards deliver unforgettable nights of theater, music, comedy, and film, perfect for friends, family, coworkers, and every arts lover on your list.

Free

Haddam Historical Society Online Holiday Auction

online

Discover unique gifts, local experiences, art, and festive treats at the Haddam Historical Society’s online holiday auction, a joyful way to find perfect presents while supporting essential programs and museum care.

Burgers, Bourbons & Brews

Brushmill by the Waterfall 129 W Main Street, Chester

Experience a refined take on burgers every Thursday at Brushmill By the Waterfall in Chester.

GOSC December Holiday Events

Various Locations in Old Saybrook

Kick off the holidays in Guilford. Enjoy Ladies Night shopping and prizes, the family-fun Stocking Walk filled with treats, and the weeklong Elf Hunt adventure for festive prizes and cheer.

Free
Ongoing

Winter Wreaths & Graceful Garlands – Bring home the season!

Village Herbery 14 Union Street, Deep River

Deck your halls with handmade charm. Village Herbery’s Magnolia and Winter Wreaths, garlands, and vintage treasures arrive Thanksgiving weekend, festive, fragrant, and full of holiday spirit. Discover your new seasonal favorite.

Free

Playhouse Holiday Jamboree at Ivoryton Playhouse

Celebrate the season at Ivoryton Playhouse’s Holiday Jamboree, a joyful mix of music, stories, and hometown cheer. Six dazzling performers deliver heartwarming fun that invites you to sing along and share the holiday spirit.

$60

Holiday Afternoon Tea at Westbrook Inn

Westbrook Inn Bed & Breakfast 976 Boston Post Rd, Westbrook

Sip, snack, and soak in the season. Enjoy festive Christmas teas, towers of treats, and fireside vibes at the beautifully decorated Westbrook Inn. The ultimate cozy holiday afternoon awaits.

$40

Welcome to Santa Claus, the Musical!

Milford Arts Council 40 Railroad Avenue, Milford

Get ready for 100% merry fun. Pantochino’s Welcome to Santa Claus is a joyful, laugh-out-loud holiday musical where Christmas never ends, and Santa himself saves the day. Bring snacks, cheer, and friends.

$35

CraftWestport

Staples High School Fieldhouse 70 North Avenue, Westport

Shop small, shop special. CraftWestport brings together 175 artists and makers offering unique art, jewelry, home décor, and more. A one-of-a-kind shopping experience perfect for holiday gifting.

$13

Tea with Santa

Old Lyme Inn 85 Lyme Street, Old Lyme

Santa’s stopping by the Old Lyme Inn on two Saturdays this year. Celebrate with a festive afternoon tea, holiday sweets, and photo ops galore in this cozy, magical kickoff to the season.

$45

Musical Masterworks presents Edgar Meyer and Amy Yang

The First Congregational Church of Old Lyme 2 Ferry Road, Old Lyme

Experience an extraordinary performance as Musical Masterworks welcomes virtuoso bassist Edgar Meyer and pianist Amy Yang for a genre-bending journey of classical gems, fresh arrangements, and Meyer’s own breathtaking creations.

$45

Santa and Mrs. Claus at Saybrook Home

Saybrook Home 2 Main St, Old Saybrook

Snap a magical moment with Santa & Mrs. Claus. Head to Saybrook Home’s Old Saybrook Showroom for smiles and memories to treasure.

Free

Cappella Cantorum Winter Concert

John Winthrop Middle School 1 Winthrop Road, Deep River

Celebrate the season with music. Join Cappella Cantorum and Orchestra for Bach’s Magnificat and festive favorites, featuring stellar soloists, an unforgettable holiday concert to lift your spirits and your heart.

$32

Westbrook Annual Tree Lighting and Holiday Parade

Westbrook Town Green

Light up your holidays at Westbrook’s Tree Lighting & Parade. Enjoy carriage rides, Santa visits, live music, ice carving, crafts, snacks, s’mores, and community cheer—all totally FREE. Don’t miss it.

Free