Last updated: November 11, 2024
Experience the excitement of the holidays in Fairfield! Our guide has everything you need for a festive season. Whether you're a familiar face or a new visitor, our guide ensures you experience the holiday spirit of Fairfield.
One highlight this season is the 16th Annual Greenwich Reindeer Festival & Santa's Workshop, where children can meet Santa and his reindeer in a picturesque holiday setting. For those seeking a dazzling display, the Magic of Lights at Pratt and Whitney Stadium features stunning illuminated displays that bring joy to all ages. And the Stamford Holiday Stroll at Mill River Park is something you definitely don't want to miss, offering a charming atmosphere with local vendors and live entertainment. See more details on these and other fun events and activities below!
Contact information and details below.
Interactive 30-foot Christmas tree and dazzling light displays.
At Mill River Park, Stamford, the Holiday Stroll offers a light-filled outdoor experience with interactive displays, 30-foot Christmas trees, and festive food vendors.
Where: Stamford | More Info: Stamford Holiday Stroll at Mill River Park
Holiday hayride with Santa and festive lights.
At Fairview Tree Farm, experience a 30-minute tractor-pulled hayride through decorated and lit tree fields and holiday scenes. Visit Santa, Mrs. Claus, and the Grinch while enjoying holiday spirit and cozy bonfires. This event is perfect for families and offers a unique holiday experience.
Where: Shelton | More Info: Night of Lights Merry Christmas Hayride at Fairview Tree Farm
Dazzling nighttime light display with accompanying audio.
Fantasy of Lights at Lighthouse Point Park is a dazzling holiday light display featuring seasonal shapes and characters, accompanied by holiday music and information about the display. The event supports Goodwill of Southern New England's mission to strengthen communities by supporting individuals of all abilities through person-centered employment, training, and services.
Where: New Haven | More Info: Fantasy of Lights at Lighthouse Point Park
Unique gifts crafted by local artists.
The Rowayton Holiday Gift Show features original, handcrafted works by local artists, including holiday and non-holiday items.
Where: Rowayton | More Info: Rowayton Holiday Gift Show
Unique gifts and home decor from local artisans.
The Fairfield Holiday Pop-Up Market is a vibrant event featuring a diverse array of local artisans and vendors showcasing handmade gifts, home decor, and unique items. This festive market offers a wonderful kick-off to the holiday season with special preview and shopping days.
Where: Fairfield | More Info: Fairfield Holiday Pop Up Market
Large-scale holiday craft fair with over 145 vendors.
Frosty's Christmas Craft Festival is a large holiday craft fair featuring approximately 145 talented crafters and vendors showcasing handmade goods and products. The event takes place at the Aqua Turf Club in Southington, CT, offering a variety of food items for purchase. Admission is $5 for adults, with children 16 and under entering free with a parent.
Where: Southington | More Info: Frostys Christmas Craft Festival
Unique holiday shopping experience with beautifully decorated trees and high-end raffle prizes.
The Danbury Festival of Trees is Greater Danbury's signature holiday event, featuring a forest of decorated trees, high-end raffle prizes, boutique and quilter's corner gift shops, and a crafts fair.
Where: Danbury | More Info: Danbury Festival of Trees
Unique holiday shopping experience in a historic setting.
The Holiday Boutique In The Barn at Keeler Tavern Museum features a variety of local artisans and vendors selling handmade gifts and seasonal items. Visitors can explore period rooms and enjoy fun activities like a partridge scavenger hunt and take-home crafts.
Where: Ridgefield | More Info: Holiday Boutique In The Barn - Keeler Tavern Museum
Unique gifts and live music by School Rock.
The Holiday Market at New Canaan Nature Center offers a variety of unique gifts, including jewelry, clothing, and candles, with School Rock providing holiday cheer. Participating vendors include Beauty Counter, Burkewood Road, Robert Karl Art, and more.
Where: New Canaan | More Info: Holiday Market- New Canaan Nature Center
Unique handmade gifts and local artisans.
The Holiday Pop-Up Market at the Fairfield Museum and History Center is a vibrant gathering of artisans and vendors offering unique handmade gifts and home decor items. This event serves as a delightful kick-off to the holiday season, featuring a special preview night and a variety of local artisans showcasing their talents.
Where: Fairfield | More Info: Holiday Pop-Up Market- Fairfield Museum and History Center
Historic train rides with scenic views.
Celebrate the holiday season with scenic train rides through the picturesque Naugatuck River Valley, offering a nostalgic and educational experience.
Where: Thomaston | More Info: Holiday Train Rides at Railroad Museum of New England
Classic tale of redemption with intricate set design.
Downtown Cabaret Theatre presents A Christmas Carol, a classic tale of redemption and transformation, featuring a talented cast and intricate set design.
Where: Bridgeport | More Info: A Christmas Carol at Downtown Cabaret Theatre
Giant helium balloons and diverse entertainment.
The Stamford Downtown Parade Spectacular is one of the largest helium balloon parades in the country, featuring giant balloons and various entertainment groups.
Where: Stamford | More Info: Stamford Downtown Parade Spectacular
Live reindeer interaction and family-friendly activities.
The 16th Annual Greenwich Reindeer Festival & Santa's Workshop is a cherished town tradition where families can meet Santa, interact with live reindeer, and enjoy various activities like the Reindeer Coloring Station and Letter Writing to Santa Station. The event supports Kids in Crisis and offers free parking.
Where: Greenwich | More Info: 16th Annual Greenwich Reindeer Festival & Santa's Workshop
Meet Santa in a historic trolley setting.
Visit with Santa at The Shore Line Trolley Museum offers a unique holiday experience where children can meet Santa amidst historic trolleys and scenic settings.
Where: East Haven | More Info: Visit with Santa at The Shore Line Trolley Museum
Immersive virtual train ride to the North Pole with interactive themed rooms.
Holiday Wish Express at Stamford Town Center offers a virtual train ride to the North Pole, featuring interactive themed rooms, holiday magic, and memorable characters. Explore over 20,000 square feet of awe-inspiring Christmas fun, including Glacier Island, the Enchanted Twinkling Forest, and Santa's Workshop.
Where: Stamford | More Info: Holiday Wish Express at Stamford Town Center
Family-friendly holiday event with diverse activities.
North Haven Winterfest features over 30 local craft vendors, face painting, free kids' crafts and games, story time, food trucks, hayrides, tree decorating, basket raffles, and a touch-a-truck experience. Meet Santa and take photos with your family.
Where: North Haven | More Info: North Haven Winterfest
Meet Santa and enjoy activities for kids.
The North Haven Holiday Fair at the North Haven Fairgrounds features Santa, activities for kids, and vendors, making it a fun event for the whole family.
Where: North Haven | More Info: North Haven Holiday Fair
Interactive historical exploration with costumed interpreters and family-friendly activities.
Explore the centuries-old Keeler Tavern Museum during the Holiday Stroll Open House. Costumed interpreters will share stories about the site's former residents, and fun activities like a partridge scavenger hunt and take-home crafts will engage younger visitors. The event features period rooms reflecting historic traditions and ways of living from the 18th, 19th, and 20th centuries.
Where: Ridgefield | More Info: Holiday Stroll Open House - Keeler Tavern Museum
Interactive holiday activities with Santa and a giant model train.
The New Canaan Nature Center transforms into a vibrant holiday event with activities like visits with Santa, holiday trains, campfires, gingerbread decorating, and more. Enjoy festive activities for the entire family.
Where: New Canaan | More Info: Winter Wonderland- New Canaan Nature Center
Hands-on holiday baking for kids with take-home recipes.
Join Pam Buchler from Aquarion Catering for a series of baking workshops at Edmond Town Hall. Each week, kids aged 8-12 will learn to make different holiday treats, including sandwich cookies, holiday cookie decorating, hot chocolate ice box mini pies, and chocolate orange pudding with vanilla cake. They will take home recipes and enjoy some samples.
Where: Newtown | More Info: Baking Workshop for Kids at Edmond Town Hall
Holiday celebration with luminaria, lanterns, and outdoor fires.
Gather around outdoor fires at Connecticut's oldest house to enjoy roasted marshmallows, popcorn, hot cocoa, and mulled cider. Listen to readings of The Night Before Christmas and craft a punched tin paper lantern to take home. Explore the archaeology exhibit History Beneath Our Feet and shop in the museum gift shop.
Where: Guilford | More Info: Henry Whitfield State Museum, Guilford - Firelight Festival
