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Last updated: November 11, 2024

Celebrate the magic of the season in Waterbury with our ultimate guide. From those who know Waterbury's secrets to those eager to uncover them, our guide reveals festive treasures.

One highlight of the holiday season is the Waterbury Holiday Craft Fair, where local artisans showcase a variety of handmade gifts and seasonal decorations. Additionally, the Stonington Holiday Stroll & Marketplace offers a charming atmosphere, featuring unique boutiques and delicious treats. And the Norwich Winterfest & Christmas Market is something you definitely don’t want to miss, presenting a lively blend of entertainment and holiday shopping. See more details on these and other fun events and activities below!

Contact information and details below.

Waterbury Holiday Markets and Shopping

What to Expect:

Indoor holiday gift expo with 200 vendors and Santa visits.

Description:

The Waterbury Christmas in Connecticut Holiday Gift Expo features 200 handcrafted and commercial vendors, offering a variety of gifts and seasonal items. Children can visit Santa and receive a treat, while a few food trucks will be available outside. This is an indoor event.

Where: Waterbury | More Info: Waterbury Christmas in Connecticut Holiday Gift Expo

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What to Expect:

Local artisans selling handmade goods.

Description:

The Waterbury Holiday Craft Fair is a vibrant event featuring local artisans and vendors selling handmade goods, including jewelry, baked goods, decorative items, and more. Bring the kids to get their photo taken with Santa and enjoy door prizes.

Where: Waterbury | More Info: Waterbury Holiday Craft Fair

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What to Expect:

Unique gifts from hundreds of American artists.

Description:

The Guilford Holiday Fest at the Guilford Art Center features handcrafted holiday gifts from hundreds of American artists, including accessories, candles, ceramics, clothing, and more. Shoppers can find unique items and support local artists while enjoying a variety of shopping experiences.

Where: Guilford | More Info: Guilford Holiday Fest

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What to Expect:

Celebrating community traditions with beautifully decorated trees and diverse cultural performances.

Description:

The Danbury Festival of Trees is Greater Danbury's signature holiday event and Ann's Place's biggest fundraiser. It features a forest of decorated trees, high-end raffle prizes, boutique and quilter's corner gift shops, live entertainment, and children's activities.

Where: Danbury | More Info: Danbury Festival of Trees

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What to Expect:

Indoor marketplace with local crafters and vendors.

Description:

The Santa's Elves Marketplace at Meriden Mall features local crafters and vendors selling handmade goods and unique holiday gifts. The event spans six weekends, offering a variety of items for shoppers to explore.

Where: Meriden | More Info: Santas Elves Harvest Marketplace

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What to Expect:

Unique handmade gifts from local artisans.

Description:

The Vernon Holiday Artisan Fair at Arts Center East features over 60 local and regional artisans showcasing unique handmade items such as soaps, lotions, candles, jewelry, stationery, ceramics, wood crafts, textiles, and home decor.

Where: Vernon | More Info: Vernon Holiday Artisan Fair

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What to Expect:

Large event space with multiple vendor stalls and dining options.

Description:

The Stamford Christmas in Connecticut Holiday Gift Expo is a two-day event featuring over 75,000 square feet of space at Chelsea Piers. Attendees can explore various vendors selling crafts, gifts, and seasonal items. The event includes a house restaurant and bar, offering a convenient dining experience.

Where: Stamford | More Info: Stamford Christmas in Connecticut Holiday Gift Expo

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What to Expect:

Unique holiday shopping experience with local vendors and festive activities.

Description:

The Terryville Christmas Bazaar at Terryville Congregational Church features vendors selling a variety of items, including Christmas gifts, food, and baked goods. The event also includes a Cookie Walk and a Christmas Past Room.

Where: Terryville | More Info: Terryville Christmas Bazaar

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Waterbury Holiday Shows and Entertainment

What to Expect:

Classic adaptation with a diverse cast and special effects.

Description:

A Christmas Carol at Hartford Stage brings Charles Dickens's timeless tale to life with Ebenezer Scrooge, Tiny Tim, and the ghosts of Christmas Past, Present, and Future. Directed by Michael Wilson, this production features a talented cast and creative team, ensuring a heartwarming and engaging holiday experience.

Where: Hartford | More Info: A Christmas Carol at the Hartford Stage

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What to Expect:

Youth-led production of Elf Jr. The Musical.

Description:

Young performers ages 7-14 bring Elf Jr. The Musical to life at the Warner Theatre, led by industry professionals who teach storytelling, character development, and collaboration while building confidence.

Where: Torrington | More Info: Elf at the Warner Theatre

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Waterbury Other Holiday Activities

What to Expect:

Seasonally decorated train with visits from Santa and his elves.

Description:

The Santa Express is an afternoon train ride where families can visit Santa Claus and his elves. Each child receives a special gift from Santa's toy bag, and passengers enjoy hot chocolate and festive decorations.

Where: Thomaston | More Info: Santa Express

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What to Expect:

Personalized gift-giving experience with Santa and Mrs. Claus.

Description:

All Aboard the Snow Clipper offers a personalized gift-giving experience where Santa and Mrs. Claus hand out the first gifts of Christmas. The event includes a visit to the Danbury Railway Museum, where kids can enjoy the museum interior, including a Letters to Santa coloring station and operating model railroads. After a short train ride through the historic Danbury Railyard, families meet Santa and Mrs. Claus for a no-rush meet and greet. The event concludes with a walk through the railyard, enjoying hot chocolate, marshmallows, and fresh baked cookies.

Where: Danbury | More Info: All Aboard the Snow Clipper

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What to Expect:

Haunted trolley ride with paranormal investigations.

Description:

The Connecticut Trolley Museum offers a variety of events throughout the year, including the "Curse of the Rails" haunted trolley ride, the "Pumpkin Patch" family fun day, and holiday festivities like "Winterfest and the Tunnel of Lights." These events provide a unique blend of history, entertainment, and seasonal activities for visitors of all ages.

Where: East Windsor | More Info: Holiday Express Train Show

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