Strolls & Tree Lightings


Holiday strolls in Shoreline villages feature Santa visits, sleigh rides, caroling, tree lightings and special events in the shops.

Niantic Holiday Stroll on 11/25, 3 – 7pm: Enjoy store specials, sales and giveaways while shopping local this Small Business Saturday from 3pm to 7pm. Stop by the Food Truck court to warm up with delicious bites. Go on the hunt for some mischievous elves in the shop windows with the Mermaid Elf Trail.

Madison Small Business Saturday and Santa Comes to Town  on 11/25, 11:15-6pm: Small business Saturday comes to Madison the Saturday following Thanksgiving. Come down and stroll the shops see what they have to offer this holiday season!! Santa will ride down Main Street to the steps of Cafe Allegre, where he will listen to all the boys and girls holiday wishes. Find out more.

New Haven Tree Lighting & Holiday Village  on 11/30, 5:30pm: Join the Elm City as they kick off the holiday season with their official Tree Lighting Ceremony & Holiday Village on the New Haven Green. The Tree Lighting Ceremony will feature entertainment, photo opportunities with Santa & Mrs. Claus, and many more surprises for the whole family! This event is family-friendly, and pet-friendly with retail products by local entrepreneurs perfect for holiday gifts. The Holiday Village runs through the weekend. Details here. 

Stonington Lobster Trap Tree at Stonington Town Dock  11/25 – 1/9: Lit from 4:30 to 9:30pm through January 9

Stonington Village Holiday Stroll on 12/1, 5:30pm: Every year, on the first Friday evening in December, the Stonington Village Improvement Association (SVIA) sponsors a tree lighting ceremony in Wadawanuck Square that includes a community carol sing and a special visit by Santa. Immediately following the lighting of the tree is the annual holiday stroll down Water Street.

First Friday in Chester and Starry Nights  on 12/1, 5 – 8pm: Join the Merchants of Chester for an extra special First Friday celebration! In addition to new exhibitions, seasonal menus & ice cream flavors, live music and great shopping, the Star installation will be lit, all at once at 5:45pm! Visit the Chester website.

Guilford Tree Lighting, 12/1, 5:45-6:30pm on the Town Green. Music performances, Santa visit & more. Get details here.

Ivoryton Illuminations, 12/2 and continuing throughout December: Visit the brightest village in Connecticut throughout December as Ivoryton lights up with over 400,000 lights! Sponsored by the Ivoryton Village Alliance.

Westbrook Holiday Parade and Tree Lighting on 12/3, 4pm: Join the fun on this annual Holiday Parade and Tree Lighting including Santa and Mrs. Claus, Ice Carving, Crafts and reindeer food, S’mores at the bonfire, Horse-drawn carriage rides and much more abundant good cheer. Get the details. 

Christmas in the Village, East Haddam, 12/5
Santa will fly into the Goodspeed Airport to help celebrate the season in the village of East Haddam. 

Old Saybrook Starlight Festival on 12/2: Centered on the Town Green, this day-long family friendly event will have you feeling merry & bright! Activities include: Meet with Santa, a Stocking Walk, Story Time, dance performances and more. Get details.

The Deep River Annual Holiday Stroll and Holiday Light Parade on 12/2, 4-7pm: Visit local merchants for festive cheer and specials. Festivities include CT Yuletide Carolers, DR Historical Society’s Festival of Trees, Tree Lighting, Visit from Santa, Gingerbread House Contest, Fire Performer and Inflatable Snow Globe and more. Find out more.

Downtown Mystic Holiday Stroll & Luminaria on 12/5 from 5 – 9pm: Stroll the festive streets of Historic Downtown Mystic and listen to the carolers rejoice in the holiday spirit as Santa makes his way through the hustle and bustle! Merchants will keep their shops open late so everyone can get a head start on their holiday shopping while enjoying hot cider, cookies and other goodies in the stores. This is a community event, free of charge and open to the public.

Holidays at Gillette Castle State Park, East Haddam
 See the Castle in all its holiday splendor with a slew of special events. Check the schedule here.