You’re floating above a Christmas tree. From here, the star topper glows at the center, not the peak, and the branch ornaments twinkle around it, not below. You float a little forward and look back at an angle, with one side of the tree now mostly hidden.
Now imagine the star is New Haven, and the ornaments you can still see are neighboring towns and cities, and the emptiness now formed by the hidden edge of the tree is the Long Island Sound. In other words, imagine a map of the area, but with cities and towns connected like a constellation by wraparound lights or festoons of tinsel, starting from New Haven and spiraling loosely outward.
That spiral tracks the order in which I’m mapping this year’s local Christmas tree lightings.
We begin, of course, in New Haven, whose official tree lighting festival happens Thursday, December 4, from 5 to 8 p.m. Attendees can expect live music, food, carousel rides, photo ops with Santa and, if history repeats, an emceed program geared more toward the TV audience than the crowd gathered ’round on the New Haven Green.
The second point of our spiral is Hamden, whose 2025 tree lighting, from 5:30 to 7 on Wednesday, December 10, promises cocoa, caroling and Christopher Kringle in Town Center Park.
Over in North Haven on Sunday, December 7, a blizzard of activity starting at 3 p.m.—“selfies with Santa, holiday crafts, games, and performances”—fills the town rec center. Then, at 4:30, it’s off to the town green, to light the tree and get caroled away.
Starting at 6:30 on Friday, December 5, North Branford packs a Santa-sack’s worth of attractions into its 90-minute tree lighting festival on the town’s “Augur Property”: food trucks, ice sculpting, hayrides, marshmallow toasting, hot chocolate, performances and another appearance by Santa.
Branford’s annual tradition incorporates a festive and charitable parade, which steps off from Branford High School this Saturday, November 29, at 6:30 p.m. It marches to the town green, where the lighting is scheduled for 7:15, with attendees encouraged to bring non-perishable items to donate to a town food drive.
Also this Saturday, and also encouraging a donation (this time for a toy drive), East Haven’s annual tree lighting festival, from 1 to 5 p.m. on the town green, gathers Santa, carriage rides, local entertainment, cookies to decorate, hot cocoa to drink and kid-friendly crafts.
Swooping back around over the harbor, our Christmas constellation lands in West Haven, which is also holding its annual tree lighting this Saturday, November 29. Starting at 4:30 p.m. on the town green, attractions include live entertainment, family-friendly activities, hot chocolate, Santa’s village and, come 6, Santa too.
The town of Orange turns red and green on Saturday, December 6, from 3 to 6 p.m. After a gingerbread house contest, a Victorian Christmas and toy shop, a local history railroad display and food trucks/a DJ at various locations, a large parade of lighted tractors heads to the town green (at Orange Center Road and Meetinghouse Lane), where a 5:30 tree lighting is preceded by Santa’s arrival.
The night before, from 5 to 9 p.m. on Friday, December 5, northerly Shelton attracts both Mr. and Mrs. Claus to its Community Tree Lighting & Holiday Market. Located in Veterans Memorial Park, the gathering also convenes local artisans and entertainers, alongside free cocoa and cookies, community bonfires, mobile food and drink vendors and, through a toy drive, a chance to feel the true spirit of Christmas.
Neighboring Derby, our small state’s smallest town by land area, wastes little time lighting its tree. Starting at 5 p.m. this Friday, November 28, festivities on the town green feature holiday singing by local church and school choirs, plus “hot chocolate, candy canes, and a visit from Santa.”
From 4:30 to 7:30 in downtown Seymour, the American Legion outpost hosts the town’s tree lighting and also hosts visits with Santa, who’s apparently arriving at 6:15 by train, not sleigh. “Enjoy pictures with Santa, a petting zoo and pony rides (5:30 to 7:30 p.m.), letters to Santa at Town Hall, food, drinks, and more!… We’ll also be collecting donations for Toys 4 Kids and non-perishable food items.”
Cheshire’s annual Winter Wonderland in Bartlem Park promises a “holly jolly evening” of “live music, goats, carolers, games, hot cocoa, cookies, ice carv[ing], hayrides, kiddie train [rides and] fun characters” from 3 to 5:30 on Sunday, December 7.
On Saturday, December 6, the day after a big holiday shopping event, downtown Wallingford turns into a winter wonderland of its own. From 1 to 5 p.m., activities centered in and around Town Hall include visits with Santa, train rides, cookie decorating, arts and crafts, carriage rides, games, “photo ops with our storybook friends,” ice carving, chestnuts roasting, goodie bags, holiday music and sweet treats galore. Then, at 5, a procession heads several blocks to Johanna Manfreda Fishbein Park, where live holiday music and Santa’s arrival herald the lighting of the city tree, with additional photo ops after the tree’s alight.
Having already hit North Branford, the spiral’s next stop is Guilford, where a schedule of activities about as long as Wallingford’s but noticeably more quaint—from a chili supper to a book sale to a candlelight walk to local student concerts to a firelight festival at Connecticut’s oldest house to a next-day breakfast with Santa—spirals in turn around the actual tree lighting, between 5:45 and 6:30 p.m. on Friday, December 5, as well as its location, the town green.
Hitching a ride on Santa’s sleigh, we round back west to Milford, where, before the tree lighting on the green this Friday at 6:30 p.m., a German-inspired Christkindlmarkt featuring 70 of “the area’s best artisans” starts at 1 and the Grinch steals Christmas (“with a special appearance from the Grinch” in person) at 3:30.
We’ve now spiraled all the way to the bottom branch of our Christmas tree, but we’re not quite finished. Tracking back east on a line that’s as taut as an overstretched Christmas light cord, we arrive at our final stop, which in some ways actually resembles a sparking socket: Madison. First, at the Madison Beach Hotel this Saturday starting at 4 p.m., revelers enjoying “complimentary hot cocoa, hot cider and live holiday themed music” (and a cash bar for adult beverages) will light a bonfire and, at 5, a tree. The town’s official lighting, held on the town green, comes almost a week later, from 5:30 to 7:30 on Friday, December 5. “Join Santa and friends for a festive evening” featuring carriage rides, hot cocoa and what sound like free s’more supplies. The topper is a holiday concert from The Spizzwinks, an a cappella group based at Yale right here in New Haven.
Which you could say, as a wrap-up to this roundup, brings our Christmas tree spiral full circle.
Written and photographed by Dan Mims. Video captures the moment of the 2021 New Haven tree lighting. Readers are encouraged to verify times, locations and other details before attending events.
