All Weekend 

Ridgefield Holiday Stroll (Fairfield County)
Discover the beauty and splendor of Downtown Ridgefield while strolling the streets listening to roving carolers or riding though the illuminated Downtown in a horse-drawn carriage. In addition to the music and carriage rides, some traditional Stroll favorites are back including ice sculpting, photos with Santa and Mrs. Claus, and children’s performances at the Ridgefield Library, along with in-store raffles, holiday promotions and refreshments offered at the many local businesses and organizations. Friday to Saturday. Free.

Fairfield Christmas Tree Festival (Fairfield County)
See the historic Burr Homestead in Fairfield, Connecticut magically transformed into a celebration of the Christmas season. Visitors may enjoy a cup of complimentary hot cider as they roam the mansion and view the rooms designed by local interior decorators and artists and kids can visit with Santa. (Kids can also register for the "Let's Build a Snowman" workshop on Friday, additional fees apply.) Thursday to Sunday. $10 adults; $5 children.

Santa's Crazier Christmas at the Bijou (Fairfield County)
Santa Claus is returning to The Bijou. In this fun-filled interactive sequel to last year’s “Santa’s Crazy Christmas” guests can expect a cheerful experience from the moment they walk in! Walk into a winter wonderland full of friendly elves, Christmas treats and refreshments – including hot apple cider, mulled wine (for the adults), cookies and milk, and even reindeer food! Then stop by the decorating table where you can create your very own commemorative ornament! Once in the theater, you will follow along as Santa reads a classic tale – but you just might find that the Jolly Old Saint Nick will needs help to save Christmas this year – and you become part of the show! $15 per ticket. Saturday and Sunday through December 21st.

Tree Lighting and Elf Workshop at Stepping Stones (Fairfield County)
On Thursday night from 5 to 8 pm admission to the museum will be free for the annual Tree Lighting event. Enjoy special seasonal exhibits including sock skating and the play-size igloo. On Friday and Saturday from 11 am to noon, you can join the Elf Workshop and spend time with Santa’s helpers for a fun-filled holiday experience! Daily (except Sunday and Monday) through December 18th. Included with museum admission.

Lamplight Stroll in Milford (New Haven County)
Enjoy a Classic New England Tradition at the 13th Annual Downtown Milford Lamplight Stroll. Visitors will enjoy a nostalgic weekend during the popular classic New England weekend that includes free horse and carriage rides, Christmas holiday carolers, the Christian Cornerstone Choir and the Senior Center Chorale Group, Christmas Spirit of Milford Ghost Walks, Santa's arrival via train, facepainting with Jammie the Gentle Clown, and more. Friday and Saturday. Free.

Winterfest at Bushnell Park (Hartford County)
Did you know there is FREE skating 7-days a week at Winterfest on the east side of Bushnell Park over by the Pump House? If you don’t have your own skates, Winterfest has free skate rentals too. Presented by iQuilt and the City of Hartford, this event also includes photos with Santa, food vendors, and more. 11 am – 8 pm daily until February 1, 2015. Free.

A Christmas Town Festival (Litchfield County)
Experience an old-fashioned Christmas celebration all around the Bethlehem Green. There will be musical performances, a tree lighting, photos with Santa, horse-drawn hayrides, shopping, a book and bake sale, crafts and gifts galore (indoors and out), food and refreshments, strolling carolers, and holiday characters, Santa's workshop, and activities for the whole family. You may also want to plan a visit to the nearby Regina Laudis Abbey Creche, which we recently reviewed here. Friday and Saturday. Free.

Annual Christmas Festival Weekend (Litchfield County)
Gingerbread Nativity Making, Candlelight Carol Sing, and a re-enactment of the Nativity with live animals, little angels, shepherds, and choristers will take place over the weekend. Check event listing for specific times. Saturday and Sunday. $5 suggested donation.

Saturday, December 6

Fresh Beat Band at the Oakdale Theatre (New Haven County)
The beat is back! The Fresh Beat Band returns to the Toyota Oakdale Theatre with their "Greatest Hits Live" tour. Showtime is at 5:30; all children over one year old require a ticket. Tickets range from $27 to $37.

Windsor Locks Annual Torchlight Parade (Hartford County)
Beginning at 6 pm the parade will line up at Noden Reed Park, then proceed from Spring Street to Center Street to Church Street. The Tree Lighting Ceremony will take place immediately following the parade at the Windsor Locks Town Hall where there will be entertainment and refreshments. Santa will be at Town Hall to hear all of your Christmas wishes! Free. 

4th Annual Celebration of Young Photographers (Litchfield County)
A unique exhibit of 60 images by young and talented photographers from across the NW region of Connecticut will be displayed at the Litchfield Historical Society. Following the exhibit there will be an event celebrating the selected top young photographers. Cookies, crudites, apple cider and wine will be served. Free.

Around the World: Sweden (Fairfield County)
Head to Stepping Stones for their monthly program exploring the culture and music of different countries around the world. This month the focus is on Sweden and the ABBA Girlz, the ultimate ABBA tribute band! Enjoy classic ABBA covers with full costumes and choreography. The ABBA Girlz duo is a blast from the past sure to delight the whole family! Included with museum admission.

Sunday, December 7

Rowayton Community Association Santa Run (Fairfield County)
Santa’s making his annual visit to Rowayton aboard his big red Fire Engine sleigh. Santa will start at the Rowayton train station at 1:00pm and then stop at spots around town including Rowayton Library and Brendan's 101. Children who miss Santa on his rounds can visit him at the Fire House from 2:15-2:45pm. Please bring a new, unwrapped toy, gift card or other gift (appropriate for ages 4 to 13) to hand to Santa during his run. Toys will be donated to the George Washington Carver Center in South Norwalk. Free.

Heights and Lights  (Fairfield County)
From 22 stories high above Stamford Downtown, watch and cheer for Santa Claus and guest rappellers Brian Cashman and Bobby Valentine, as they make a daredevil descent, twisting and flying from the top of one of Stamford’s tallest buildings, Landmark Square. Then follow Santa up Bedford Street to Latham Park for an evening of holiday fun with live music with the the cast of Peter Pan, Jr. from Saxe Middle School and join in the countdown of the annual lighting of Stamford’s Holiday Tree. Free. 

Polar Plunge at Lake Waramaug (Litchfield County)
Come do the coolest thing you'll do all year! Splash into the (chilly) waters of Lake Waramaug in support of a great cause! The Polar Plunge for Partnership is the annual fundraiser for the Washington Montessori School Community Partnership Program. There will be 2 plunges: one at 11 a.m. for participants 11 and up and one at 11:05 a.m. for participants 6-10. Registration and check-in will begin at 10 a.m. $20

Madison Christmas Parade (New Haven County)
Head to the center of Madison to watch the holiday parade beginning at 4:15 pm. The parade will include music, pets, local sports teams and groups, and, of course, Santa too! Then follow the parade to the Tree Lighting Ceremony--the way will be lit with luminaries with the help of Madison’s own Boy Scout Troop 490 which will also be providing hot chocolate. Les Julian will provide holiday music. Free.

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Have a wonderful weekend!