5 Nearby Winter Festivals in Connecticut

There’s no denying that winter is beautiful in these parts. Whether you love the season or simply tolerate it, these nearby Connecticut winter festivals can make the chillier months of the year fun for everyone.

November: Holiday Lighted Boat Parade in Mystic, Conn.

Santa Claus is coming to town, but maybe not quite as expected. Just a short drive from Old Saybrook, enjoy the Holiday Lighted Boat Parade in Mystic, where Santa gives the sleigh a break and goes with the flow on a 60-foot tug boat. After his big entrance and official Mystic River Park tree lighting, the parade boats follow. Festive vessels strut their stuff down the river runway as their crews partake in friendly competition for titles like Most Charismatic Crew, Innovative Vessel, Best Dressed Vessel, and Miss Mystic Vessel of Grandeur.

December: North Pole Express in Essex, Conn.

Bring a favorite winter fairytale to life on a North Pole Express ride. The 90-minute ride features live performances of “The Night Before Christmas” in each train cabin. Passengers can lend their voice to sing-a-longs or spend the trip sipping hot chocolate and munching on sugar cookies. The North Pole’s most famous faces are also on board, and children receive a small gift from the jolly fellow in red at the end.

January: Fire & Ice Festival in Saybrook Point Inn

Not too hot and not too cold, the Fire & Ice Festival here at the Saybrook Point Inn is just right for celebrating the winter season. This public event takes place at the Waterfront Terrace and Grand Ballroom, and highlights the contrasting elements of fire and ice with the beloved Fire Bar and a specially sculpted Ice Bar. Chilly treats include sushi, oysters, and samples of local beer and wines, while chili, chowder, and hot chocolate offer delicious opportunities to warm up. Kids and adults will be kept entertained between bites with magic shows, ice sculpting and woodcarving demonstrations, carriage rides, and more.   

February: Winter Carnivale in Chester, Conn.

Each February, the streets of downtown Chester are filled with hundreds of smiling faces, the smell of chili, and the occasional adult in a chicken costume riding a tractor. When that combination rolls into town, it can only mean one thing — the annual Winter Carnivale is back. Going on 27 years, this Connecticut winter festival enchants visitors with ice carving demonstrations, face painting, street performers, a tractor parade, and more.

February: Winterfest at Lyman Orchards in Middlefield, Conn.

At the end of February, see another side to Connecticut’s popular apple orchard and pumpkin patch. The Lyman Orchard Winterfest, a two-day event of free family fun, takes on a different theme each year. Sprinkled throughout the weekend, attendees can look forward to horse-drawn sleigh rides, contests, and games. Of course, it goes without saying that no one should leave without taking a bite out of an apple cider donut from the Apple Barrel market.

Stop by these winter festivals in Connecticut for an excuse to celebrate your favorite time of year (or a new way to appreciate it). To warm up after a long day of merriment, spend a cozy winter weekend snuggled up at Saybrook Point!