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Last updated: November 11, 2024

Experience the top holiday highlights in Guilford! Our guide showcases all the must-see events. From Guilford natives to wandering souls, our guide is your key to holiday magic.

Popular Events: The Guilford Holiday Fest invites families to enjoy an array of seasonal activities, including festive crafts and local vendors. Another delightful event features artisans showcasing unique gifts at the Waterbury Holiday Craft Fair, perfect for finding that special something. And the Stonington Holiday Stroll & Marketplace is something you definitely don't want to miss, offering charming walks through beautifully decorated streets with seasonal treats and merriment. See more details on these and other fun events and activities below!

Contact information and details below.

Guilford Holiday Markets and Shopping

What to Expect:

Community carol singing and competitive holiday window decorations.

Description:

The Stonington Holiday Stroll & Marketplace is a festive event where community carolers gather to sing Christmas carols, and Santa makes a special visit. Local merchants keep their shops open late, competing for the best window decorations in the Borough A-Glow contest. The event includes a tree lighting ceremony at Wadawanuck Square, with seasonal decorations placed around the Stonington Free Library and Cannon Square.

Where: Stonington | More Info: Stonington Holiday Stroll & Marketplace

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What to Expect:

Unique gifts from hundreds of American artists.

Description:

Guilford Art Center's Holiday Expo 2024 offers a diverse array of handcrafted holiday gifts from hundreds of American artists, makers, and designers. The event features a wide range of items including accessories, candles, ceramics, clothing, fiber art, glassware, homewares, jewelry, leather goods, Christmas ornaments, soaps, specialty foods, and stationery. The expo supports local and national talent, with new items added throughout the season.

Where: Guilford | More Info: Guilford Holiday Fest

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What to Expect:

Unique gifts from local and national artists.

Description:

The Holiday Expo at Guilford Art Center features handcrafted holiday gifts from hundreds of American artists, including jewelry, ceramics, and unique Christmas ornaments. Shoppers can explore a variety of craft categories and support local artists while enriching the community with the arts.

Where: Guilford | More Info: Holiday Expo at Guilford Art Center

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What to Expect:

Unique local crafts and baked goods.

Description:

The Waterbury Holiday Craft Fair is a festive event where local Vermont businesses showcase handmade crafts, jewelry, baked goods, and more. Bring the kids to get their photo taken with Santa, and enjoy door prizes and a variety of unique items.

Where: Waterbury | More Info: Waterbury Holiday Craft Fair

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What to Expect:

Twinkling lights and festive music create a joyful atmosphere.

Description:

Norwich Winterfest & Christmas Market offers a variety of handmade crafts, unique gifts, and delicious seasonal treats. Explore stalls at the Norfolk Showground, enjoy live performances, and meet Santa Claus amidst twinkling lights and festive music.

Where: Norwich | More Info: Norwich Winterfest & Christmas Market

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Guilford Holiday Shows and Entertainment

Guilford Other Holiday Activities

What to Expect:

Seasonally decorated train with special gifts for each child.

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. The train is decorated seasonally and offers various classes of service including coach, lounge, and premium coach options.

Where: Thomaston | More Info: Santa Express

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What to Expect:

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

Description:

Join the Danbury Railway Museum for a personalized gift-giving experience aboard the Snow Clipper. Enjoy artifact displays, model railroads, and a festive railyard with hot chocolate and cookies. Santa and Mrs. Claus will hand out the first gifts of Christmas, making it a memorable holiday event for kids.

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

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Guilford Gift Guide

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