Carriages, Candles, Starlight, And A Rappelling Santa: Here’s What’s Happening In Connecticut This Weekend

CONNECTICUT — Connecticut is officially in full holiday mode, and this first weekend of December is bursting with twinkle lights, carriage rides, historic tours, tree festivals, craft fairs, and even a Santa who rappels down a building. Whether you love small-town New England charm or big-city holiday spectacle, Dec. 5–7 offers enough festive fun to keep the cocoa flowing and your social calendar full. Here’s a merry and bright roundup of what’s happening across the state.

On Friday, Dec. 5, downtown Milford transforms into a glowing winter postcard during the Lamplight Stroll, now in its 23rd year. Visitors can enjoy horse-drawn carriage rides, holiday shopping, carolers, twinkling storefront displays, and free treats from local businesses. The stroll attracts families, couples, and anyone hoping to soak in Milford’s historic charm under lantern light. It’s one of the most beloved holiday kickoff events on the shoreline.

Also on Friday, Dec. 5, the Henry Whitfield State Museum in Guilford hosts the warm and welcoming Firelight Festival, where bonfires, candlelit paths, storytelling, marshmallow roasting, live music, and holiday crafts come together at Connecticut’s oldest stone house. It’s both festive and historic — a perfect low-key night for families or history lovers.

On Saturday, Dec. 6, Ridgefield opens its doors — literally — for the Ridgefield Holiday House Tour, where visitors can explore beautifully decorated private homes dressed in full seasonal splendor. Each stop features elaborate décor, floral displays, and creative themes curated by local designers. This self-guided tour is a fundraiser for community nonprofits and a must-see for anyone who loves interior design or holiday decorating inspiration. Not by coincidence, Ridgefield's Holiday House Tour is smack dab in the middle of the town's Holiday Stroll festivities, which begin Friday at 6 p.m. and include everything yuletide, from toy soldiers marching down Main Street, horse-and-carriage Rides, and even a Bernese Mountain dog parade.

If you’re craving a classic New England holiday celebration, waterfront-style, head to Old Saybrook on Dec. 6 for the Starlight Festival. Expect live performances, tree lighting, merchants’ specials, kids’ crafts, and plenty of hometown charm along Main Street. Local shops glow with holiday décor, making it the perfect place to start (or finish) your gift shopping.

…and really, what's the point of naming your town "Bethlehem" if you're not prepared to go all in at Christmastime? The residents of Bethlehem, CT, agree, and their Christmas Town Festival (Dec. 5–6) fills the town green with craft vendors, musical performances, hayrides, and the annual tree lighting. Families can also stop by the Bethlehem Post Office to stamp holiday cards with the famous Christmas cachet.

Running Dec. 4–14, the Festival of Trees & Traditions at the Wadsworth Atheneum in Hartford fills the galleries with artist-designed trees, wreaths, holiday décor, and themed displays. It’s part art exhibition, part holiday fundraiser — and fully enchanting.

On Saturday, Dec. 6, downtown Norwalk lights up for its 4th Annual Holiday Extravaganza, featuring a tree lighting, live music, festive food vendors, costumed characters, ice-carving demonstrations, and activities for all ages. The event runs from 4–8 p.m. and is a lively way to welcome the season.

At the Ellsworth Homestead in Windsor, Dec. 6 brings the Fantasy Forest Holiday Tour & Tree Sale, where visitors can wander through decorated rooms, sip warm beverages, buy wreaths and trees, and enjoy a scenic historic setting.

Close out the weekend Sunday, Dec. 7 in Stamford, where Santa Claus — along with a few very brave friends — rappels down the side of Landmark Square during Heights & Lights, one of Connecticut’s most spectacular holiday traditions. Following the heart-pounding descent, the event features a tree lighting, live entertainment, and plenty of family festivities.

From glowing carriage rides in Milford to daring rooftop Santa shenanigans in Stamford, Connecticut is fully illuminated with holiday cheer this weekend. Bundle up, grab a peppermint latte, and make the most of this magical early-December stretch.