Winter Festivals and Fairs to Enjoy in Connecticut

Staying at home when cold weather hits is what some prefer. However it is so much less lonely to get out and do some socializing. What better way than to visit the winter festivals and fairs around Connecticut! This is the ideal opportunity to get out and see neighbors and friends and even meet new like-minded folks, and for guys like me – a chance to practice my next game before the new season. There are many celebrations throughout the state in the cold months, and here are a few.


You still have time to make plans to get to Stratford, Connecticut and see the Oronoque Autumn Craft Festival. This takes place at the Oronoque Country Club on 3 November. Browsing hometown and local artists is always an exciting adventure as you never know what great finds you could make. Stop by and enjoy the beautiful arts and crafts.

On the 9th of November, in North Branford, the Evergreen Woods Holiday Fair is a real treat, a popular affair on the shore with plenty of delicious bakery goods for sale, as well as soaps, lotions, jewelry and stained glass. Many prefer this as their holiday shopping destination as the gifts seem much more personal when handmade.

Take the kids and head to the Holly Berry Festival in Hamden on the 22nd of November. It takes place at the Sacred Heart Academy for two days and has free admission. The children can have their photo taken with Santa! Grownups are going to love the bakery treats, the pasta dinner and all the other fun activities.

Another year has gone by and now it is the 10th annual Festival of Trees and Craft Fair in Shelton, Connecticut at Wesley Village. This event takes place on 23 November with a real celebration of the holiday season that is upon us. Christmas shopping here is a pleasure with all sorts of gifts to take home and wrap. Enjoy the many holiday treats for sale too.


The winds are blowing stronger and the snow may fly, but that is no reason to stay indoors. Get over to the Newtown Holiday Festival in Newton on the 1st of December for some extraordinary adventures. Of course, there will be craft vendors, but additional excitement may also be available! If they have a gingerbread house contest, you don’t want to miss that. You will always find delicious treats for all ages. Musical performances will enthrall young and old alike.

On the 6th of December in Harford, the LEGO KidsFest is a must for your itinerary if you have kids. It all takes place at the Connecticut Convention Center. Building with Legos can be challenging but it can be a bonding experience when the kids and their families begin to take on a creative endeavor such as this.

If you don’t have kids, or even if you do, you may prefer to head for Bethlehem, Connecticut for the Christmas Town Festival on the 6th of December. Hayrides are always a big thrill and refreshments abound. Children love to visit with Santa and have a photo shot to keep as a wonderful memory. Carolers add to the fun, and there are a number of things to do around town.


Once all your family Christmas celebrations have come to an end, you can welcome January in with a visit to the New Hope Winter Festival on January 18th and extending through to the 26th. Discover all manner of activities around Lambertville and New Hope. This is not just one day or a weekend of fun, but a full two weeks of great events and fun activities. Just some of what you can experience includes a chili cook-off, hikes, tours, ice sculptures, a fantastic parade and other family events.


On February 19 the Winter Carnivale is something you absolutely won’t want to pass up. This takes place in Chester, and it doesn’t matter what the weather is, this free event will happen regardless. Food and drink are one bonus but the street performers highlight the day. Watch a tractor parade and let the kids get face painting done. There will also be an ice carving competition that will entertain those of every age. A chili cook-off is going to be held at the Fire House on High Street. Tasting the chili and voting for your favorite means a great tasting experience for the family.


By this time, winter is almost over, but that doesn’t mean the Hebron Maple Festival should not be included in the list of fairs and festivals for winter. On March 8th in Hebron, Connecticut, this festival honors maple with a wide variety of events and activities. Everything maple here! Have you ever tried maple cotton candy? Now is the time to have this delicious treat! Arts and crafts are on display and you can get a historic church tour. Blacksmithing and woodworking demonstrations are fun for all ages. And did we mention – the ice cream eating contest? No? Well, you can’t miss that!

Enjoy your Connecticut fairs and festivals this winter!

Leave a Comment