5 Towns That Go All-Out for Christmas in New England (2025 Guide)
- Ryan Jones
- 6 days ago
- 5 min read
Why New England Is the Ultimate Christmas Destination
There’s something almost magical about a New England Christmas: historic inns wrapped in garlands, snow-dusted main streets, and lights shimmering across a village green. The combination of small-town charm and big holiday energy makes this region an ideal setting for a winter getaway. Whether you’re craving a nostalgic snowy scene or a beachfront holiday twist, New England delivers.Planning a trip for 2025 means locking in early, as boutique hotels fill fast and the best-value travel windows (typically early to mid-December or mid-week stays) tend to yield better rates. Weather varies across the region—expect true winter in Vermont and New Hampshire, while Maine and Rhode Island may lean milder—so packing layers and waterproof boots is a wise decision. With these five towns, you can craft a weekend escape that checks off festive events, cozy accommodations, and memorable photo-worthy moments.
The Best Christmas Towns in New England for 2025
1. Woodstock, Vermont – The Quintessential Holiday Village
Why Visit Woodstock at Christmas
Each December, the village of Woodstock, Vermont transforms into something out of a storybook. The 41st Annual Wassail Weekend runs December 12-14, 2025, featuring horse-drawn carriage rides, twinkling lights, and caroling on the Green. The nearby Billings Farm & Museum adds to the charm with candle-dipping, sleigh rides (weather permitting) and a Victorian-style “Christmas at the Farm” experience.
Top Holiday Events (2025)
Wassail Weekend: December 12–14, 2025.
Billings Farm Winter Celebration: includes horse-drawn wagon rides and candle-making.
Where to Stay
The Woodstock Inn & Resort – iconic, luxurious, steps from the Green.
On the River Inn – cozy boutique with riverside views.
The Shire Woodstock – charming mid-range option with local ambiance.
Make It a Weekend Getaway
Friday: Arrive and settle into The Woodstock Inn & Resort. Enjoy dinner in town and a stroll through the decorated village.v
Saturday: Dive into Wassail Weekend—catch the carriage parade at 2 pm, explore the artisan craft fair, sip hot cider on the Green.
Sunday: Grab breakfast at Mon Vert Café, take a scenic drive out via Route 12, and head home relaxed and full of holiday spirit.
2. Kennebunkport, Maine – Christmas Prelude by the Sea
Why Visit Kennebunkport at Christmas
Coastal charm meets festive flair in Kennebunkport, Maine during the annual Christmas Prelude (December 4-14, 2025). Highlights include Santa arriving by lobster boat, a tree lighting in Dock Square, and a “hat parade” where holiday hats reign supreme. It’s a slightly different holiday vibe—by the sea, with fire pits and s’mores chiming alongside more traditional elements.
Top Holiday Events (2025)
Tree Lighting Ceremony in Dock Square: Friday, December 5, 2025 at 5:30 pm.
Wave to Santa on the Lobster Boat: Sunday, December 7, 2025 at 12:30 pm.
Where to Stay
The Boathouse Waterfront Hotel – stylish, waterfront, steps to Dock Square.
Hidden Pond – luxury cottage stay, very upscale, ideal for couples.
Kennebunkport Captains Collection – yesterday’s grandeur turned elegant B&B.
Make It a Weekend Getaway
Friday: Check in, enjoy an ocean-view dinner, and stroll Dock Square under lights.
Saturday: Participate in the lobster boat arrival, take part in the hat parade, browse craft vendors, roast s’mores by fire pits.
Sunday: Brunch at Salt & Honey Café, walk the beach (if weather allows), then depart feeling refreshed and festive.
3. Newport, Rhode Island – Gilded-Age Holiday Elegance
Why Visit Newport at Christmas
In Newport, Rhode Island, the historic mansions and seaside atmosphere combine into a lavish holiday escape. The Holidays at the Newport Mansions event (November 22, 2025 – January 1, 2026) features homes like The Breakers and The Elms decorated with thousands of lights, a stunning 15-foot-tall poinsettia “tree”, and opulent holiday décor throughout. For those seeking upscale elegance, there’s no better place.
Top Holiday Events (2025)
Mansion tours during Holidays at the Mansions: daily from November 22, 2025 until January 1, 2026.
Holiday guided tours like “Behind the Scenes: The Breakers Holiday Decorations” on Thursdays December 4, 11, 18.
Where to Stay
The Chanler at Cliff Walk – boutique luxury steeped in history with cliffside views.
Hammetts Hotel – modern design near the harbor.
Francis Malbone House Inn – intimate, historic, and full of charm.
Make It a Weekend Getaway
Friday: Arrive and check-in, then enjoy a lantern-lit tour of The Breakers.
Saturday: Brunch on Thames Street, mansion tours, then ice-skate at Gurney’s Newport.
Sunday: Harbor stroll, holiday shopping at Bowen’s Wharf, then depart in holiday bliss.
4. Portsmouth, New Hampshire – Vintage Christmas by the Sea
Why Visit Portsmouth at Christmas
In the historic coastal town of Portsmouth, New Hampshire, the downtown fills with lights, trolleys and holiday cheer for their Vintage Christmas in Portsmouth . The iconic Candlelight Stroll at the Strawbery Banke Museum (December 5-7, 12-14, 19-21, 2025) invites visitors into 19th-century scenes of yuletide tradition—complete with carolers, historic homes and snow-covered walks. Combined with boutique shopping and a lively downtown, Portsmouth blends seaside atmosphere with cozy holiday magic.
Top Holiday Events (2025)
Holiday Parade & Tree Lighting: December 6, 2025 at 5:30 pm.
Candlelight Stroll weekends in December.
Where to Stay
The Hotel Portsmouth – boutique inn in the heart of downtown.
The Bow Hotel – stylish, walkable, great for couples.
Make It a Weekend Getaway
Friday: Arrive and enjoy dinner at Black Trumpet, then a stroll through Market Square.
Saturday: Attend the Candlelight Stroll at Strawbery Banke, explore boutiques, warm up with cocoa at Cup of Joe Café.
Sunday: Quick stop at Kittery Outlets for holiday shopping, then head home.
5. Taunton, Massachusetts – The Christmas City
Why Visit Taunton at Christmas
Dubbed “The Christmas City,” Taunton, Massachusetts lights up its town green and downtown with spectacular displays each December. The Lights On Festival takes place December 6, 2025, 3 PM–8 PM, and features live music, vendors, Christmas tree lighting and visits from Santa. For travelers seeking holiday charm without a long drive, this Massachusetts destination hits the mark.
Top Holiday Events (2025)
Lights On Festival & Parade: Saturday, December 6, 2025.
Santa visits Fridays–Sundays throughout December.
Bonus Ideas for Winter Weekend Getaways in New England
Extend Your Trip
Combine Woodstock + Portsmouth for a snowy inland road-trip adventure.
Pair Newport + Kennebunkport for a coastal lights itinerary that covers both luxury and seaside charm.
Add-On Experiences
Sleigh rides or Nordic skiing near Woodstock.
Ice castles or outdoor ice-skating in northern New Hampshire.
Holiday shopping stops in Portland, Maine or Boston.
Tips for Planning Your 2025 New England Christmas Trip
When to Go
Early-to-mid-December offers excellent event overlap and fewer crowds.
Mid-week stays (Sunday–Thursday) often fetch lower hotel rates and less traffic.
How to Get Around
Fly into major hubs like Boston (BOS) or Hartford (BDL) and rent a car.
Drive times between towns generally fall within 1–3 hours, making multi-stop weekends feasible.
What to Pack
Layers: base-layer, fleece, waterproof shell.
Waterproof boots, warm hat, gloves, scarf.
Portable phone charger for photo-heavy days outdoors.
Travel Advisor Insight (Book With Me)
When you book your holiday getaway with me, you’ll receive:
Complimentary itinerary design and travel concierge support.
Access to VIP hotel perks (upgrades, breakfast for two, hotel credits) at selected boutique stays.
Special holiday-season offers and insider rates for 2025.
Final Thoughts
Each of these five towns offers a unique slice of holiday joy—from Woodstock’s snow-covered village charm, Kennebunkport’s coastal lobster-boat Santa arrival, Newport’s Gilded-Age grandeur, Portsmouth’s historic Candlelight strolls, to Taunton’s festive community-lighting spectacle. Together, they form the ultimate “where to go for Christmas in New England” list for 2025.