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!
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Top Holiday Events In and Around Fairfield
- 16th Annual Greenwich Reindeer Festival & Santa's Workshop (Greenwich)
- Magic of Lights at Pratt and Whitney Stadium (East Hartford)
- Stamford Holiday Stroll at Mill River Park (Stamford)
- Holiday Train Rides at Railroad Museum of New England (Thomaston)
- Night of Lights Merry Christmas Hayride at Fairview Tree Farm (Shelton)
- Holiday Wish Express at Stamford Town Center (Stamford)
- Hebron Lions Lights in Motion (Hebron)
- Visit with Santa at The Shore Line Trolley Museum (East Haven)
- Holiday Lights Spectacular at Old Mistick Village (Mystic)
- Hartford Glow (Hartford)
See these and even more events listed below!
Fairfield Holiday Light Displays
Magic of Lights at Pratt and Whitney Stadium
What to Expect:
Dazzling drive-through holiday light displays with iconic characters.
Description:
At Pratt and Whitney Stadium, Magic of Lights features over a mile of spectacular light displays, including a 32-foot-tall animated Holiday Barbie and life-sized dinosaurs in Prehistoric Christmas. The event offers a drive-through experience with classic holiday scenes and characters, making it a memorable holiday activity for all ages.
Where: East Hartford | More Info: Magic of Lights at Pratt and Whitney Stadium
Stamford Holiday Stroll at Mill River Park
What to Expect:
Interactive 30-foot Christmas tree and dazzling light displays.
Description:
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
Night of Lights Merry Christmas Hayride at Fairview Tree Farm
What to Expect:
Holiday hayride with Santa and festive lights.
Description:
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
Hebron Lions Lights in Motion
What to Expect:
Synchronized musical experience with 1 million animated lights.
Description:
Hebron Lions Lights in Motion is a spectacular holiday light display featuring over 1 million animated lights synchronized to music, creating a 20-minute journey through 350 installations along a one-mile route. This event supports children's charities and is open to all ages.
Where: Hebron | More Info: Hebron Lions Lights in Motion
Fantasy of Lights at Lighthouse Point Park
What to Expect:
Dazzling nighttime light display with accompanying audio.
Description:
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
Hartford Glow
What to Expect:
Interactive light gardens and illuminated structures from around the world.
Description:
Hartford Glow is an indoor holiday light festival featuring interactive light gardens, illuminated structures, seasonal food and drinks, family-friendly activities, and a festive holiday market.
Where: Hartford | More Info: Hartford Glow
Holiday Lights Spectacular at Old Mistick Village
What to Expect:
Largest holiday light display in southern New England.
Description:
Olde Mistick Village is decorated with over half a million lights showcasing archways, trees, reindeer, and elves. The event is open every night from November 18 to January 31, offering a family-friendly holiday experience.
Where: Mystic | More Info: Holiday Lights Spectacular at Old Mistick Village
Winter Fest and Tunnel of Lights
What to Expect:
Holiday light display on historic trolleys.
Description:
At Winterfest and the Tunnel of Lights, over 15,000 lights illuminate the halls and trolleys. Guests ride closed trolley cars through a tunnel of lights while singing Christmas carols, and an open sleigh car offers an open-air view. The Visitor Center is decorated with model train layouts and lights galore.
Where: Windsor | More Info: Winter Fest and Tunnel of Lights
Fairfield Holiday Markets and Shopping
Rowayton Holiday Gift Show
What to Expect:
Unique gifts crafted by local artists.
Description:
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
Fairfield Holiday Pop Up Market
What to Expect:
Unique gifts and home decor from local artisans.
Description:
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
Frostys Christmas Craft Festival
What to Expect:
Large-scale holiday craft fair with over 145 vendors.
Description:
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
Danbury Festival of Trees
What to Expect:
Unique holiday shopping experience with beautifully decorated trees and high-end raffle prizes.
Description:
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
Winsted Holiday Craft Fair
What to Expect:
Unique handmade crafts and local products.
Description:
The Winsted Holiday Craft Fair at Northwestern Regional High School features over 90 vendors selling handmade crafts, local products, and items made by Ag-Ed students. This annual event is the Parents, Friends, and Alumni group's largest fundraiser, supporting the Agricultural Education program.
Where: Winsted | More Info: Winsted Holiday Craft Fair
Holiday Boutique In The Barn - Keeler Tavern Museum
What to Expect:
Unique holiday shopping experience in a historic setting.
Description:
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
Holiday Market- New Canaan Nature Center
What to Expect:
Unique gifts and live music by School Rock.
Description:
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
Indigenous Craft Fair - Mystic Seaport Museum
What to Expect:
Celebrating Native American artisans with unique, handmade crafts.
Description:
The Indigenous Craft Fair at Mystic Seaport Museum showcases hand-crafted products from regional tribes, including wampum jewelry, beaded accessories, paintings, and pottery. Visitors can also explore the Three Sisters Garden, hear talks about Indigenous mariners, and enjoy Native American fusion food.
Where: Mystic | More Info: Indigenous Craft Fair - Mystic Seaport Museum
Holiday Pop-Up Market- Fairfield Museum and History Center
What to Expect:
Unique handmade gifts and local artisans.
Description:
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
Fairfield Holiday Shows and Entertainment
Holiday Train Rides at Railroad Museum of New England
What to Expect:
Historic train rides with scenic views.
Description:
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
A Christmas Carol at Downtown Cabaret Theatre
What to Expect:
Classic tale of redemption with intricate set design.
Description:
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
Stamford Downtown Parade Spectacular
What to Expect:
Giant helium balloons and diverse entertainment.
Description:
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
Fairfield Other Holiday Activities
16th Annual Greenwich Reindeer Festival & Santa's Workshop
What to Expect:
Live reindeer interaction and family-friendly activities.
Description:
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
Visit with Santa at The Shore Line Trolley Museum
What to Expect:
Meet Santa in a historic trolley setting.
Description:
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
Holiday Wish Express at Stamford Town Center
What to Expect:
Immersive virtual train ride to the North Pole with interactive themed rooms.
Description:
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
North Haven Winterfest
What to Expect:
Family-friendly holiday event with diverse activities.
Description:
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
North Haven Holiday Fair
What to Expect:
Meet Santa and enjoy activities for kids.
Description:
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
Holiday Stroll Open House - Keeler Tavern Museum
What to Expect:
Interactive historical exploration with costumed interpreters and family-friendly activities.
Description:
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
Winter Wonderland- New Canaan Nature Center
What to Expect:
Interactive holiday activities with Santa and a giant model train.
Description:
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
Baking Workshop for Kids at Edmond Town Hall
What to Expect:
Hands-on holiday baking for kids with take-home recipes.
Description:
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
Henry Whitfield State Museum, Guilford - Firelight Festival
What to Expect:
Holiday celebration with luminaria, lanterns, and outdoor fires.
Description:
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
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Bridgeport (5 miles)
- Westport (5 miles)
- Stratford (7 miles)
- East Norwalk (7 miles)
- Trumbull (8 miles)
- Darien (12 miles)
- Milford (12 miles)
- North Stamford (15 miles)
- Shelton (15 miles)
- Stamford (16 miles)
- East Northport (19 miles)
- Smithtown (20 miles)
- Danbury (20 miles)
- Commack (21 miles)
- New Haven (21 miles)
- Huntington Station (21 miles)
- Centereach (21 miles)
- Hauppauge (22 miles)
- Lake Ronkonkoma (22 miles)
- East Haven (23 miles)
- Port Chester (23 miles)
- Coram (23 miles)
- Dix Hills (24 miles)
- Central Islip (24 miles)
- Holbrook (25 miles)
- Brentwood (25 miles)
- Branford (25 miles)
- Hamden (26 miles)
- Harrison (26 miles)
- Medford (26 miles)
- Naugatuck (26 miles)
- Deer Park (26 miles)
- White Plains (27 miles)
- North Haven (27 miles)
- Glen Cove (27 miles)
- Plainview (27 miles)
- Bay Shore (29 miles)
- Hicksville (29 miles)
- East Patchogue (29 miles)
- West Babylon (30 miles)
- West Islip (30 miles)
- Waterbury (31 miles)
- Greenburgh (31 miles)
- Cheshire (31 miles)
- Ossining (31 miles)
- Shirley (31 miles)
- Lindenhurst (32 miles)
- Guilford (32 miles)
- Copiague (33 miles)
- East Meadow (33 miles)
- Massapequa (34 miles)
- Mount Vernon (34 miles)
- Garden City (35 miles)
- Uniondale (35 miles)
- Wakefield (35 miles)
- Hempstead (35 miles)
- Peekskill (36 miles)
- Yonkers (36 miles)
- Meriden (36 miles)
- Merrick (36 miles)
- Throgs Neck (36 miles)
- Franklin Square (37 miles)
- Bayside (37 miles)
- Van Nest (37 miles)
- The Bronx (37 miles)
- Freeport (37 miles)
- Parkchester (37 miles)
- Unionport (37 miles)
- Whitestone (38 miles)
- New City (38 miles)
- Queens Village (38 miles)
- Kings Bridge (38 miles)
- Baldwin (38 miles)
- Fordham (38 miles)
- Elmont (38 miles)
- East Tremont (39 miles)
- Rockville Centre (39 miles)
- University Heights (39 miles)
- College Point (39 miles)
- Tremont (39 miles)
- Fresh Meadows (39 miles)
- Hunts Point (40 miles)
- Hollis (40 miles)
- Cambria Heights (40 miles)
- Morris Heights (40 miles)
- Morrisania (40 miles)
- Oceanside (40 miles)
- Bristol (40 miles)
- Melrose (40 miles)
- Valley Stream (40 miles)
- Washington Heights (40 miles)
- Hillside (41 miles)
- Spring Valley (41 miles)
- Englewood (41 miles)
- Kew Gardens Hills (41 miles)
- East Elmhurst (41 miles)
- Bergenfield (41 miles)
- Laurelton (41 miles)
- Rosedale (41 miles)
- Mott Haven (41 miles)
- Corona (41 miles)
- Briarwood (41 miles)
- Fort Lee (42 miles)
- Jackson Heights (42 miles)
- Rego Park (42 miles)
- Jamaica (42 miles)
- Springfield Gardens (42 miles)
- Harlem (42 miles)
- Forest Hills (42 miles)
- Richmond Hill (43 miles)
- Elmhurst (43 miles)
- Teaneck (43 miles)
- East Harlem (43 miles)
- Morningside Heights (43 miles)
- Middletown (43 miles)
- Astoria (43 miles)
- Woodside (43 miles)
- Palisades Park (43 miles)
- Long Beach (43 miles)
- Middle Village (44 miles)
- South Ozone Park (44 miles)
- Queens (44 miles)
- Cliffside Park (44 miles)
- New Britain (44 miles)
- Woodhaven (44 miles)
- Ozone Park (44 miles)
- Manhattan (44 miles)
- Hackensack (44 miles)
- Paramus (44 miles)
- Glendale (45 miles)
- Maspeth (45 miles)
- Sunnyside (45 miles)
- Howard Beach (45 miles)