Why These Holiday Getaways are Worth the Trip

These spots aren't just a string of lights; they are a full-blown holiday movie scene come to life. They offer:

• Over-the-top decorations and lights that package your whole holiday feeling into one festive place.
• Family-friendly events and dining, from tree lightings and parades to cozy, kid-approved restaurants.
• Easy day trips or magical overnights, making them perfect for a quick escape or a full-on holiday staycation.

Insider Tips for Visiting Christmas Hotels & Towns with Kids

• Book. Early. This is the number one rule for a reason. Popular festive hotels (like The Red Lion Inn) and ticketed events (like Christmas by Candlelight or the Journey to the North Pole) sell out months in advance.
• Arrive Before Dusk. Parking can be tricky in these small towns. Get there while it's still light, find your spot, explore a bit, and then watch the magic as the lights start to twinkle on.
• Check the Calendar. Many towns have one-night-only parades, caroling, or tree lightings. Check the official town or event website—and our Mommy Poppins Boston Events Calendar—before you go!
• Layer Up (and Up Again). Dress for the New England cold, especially for outdoor events. Hand warmers are a game-changer for keeping little hands (and grown-up hands) happy.
• Make it a Tradition. The best part of these family holiday getaways is the tradition. Pick a new town from this list to explore each year and watch the memories stack up.

Santa comes to Christmas towns near Boston, like North Conway, NH. Journey to the North Pole photo courtesy of the Believe in Books Literacy Foundation

Festive Hotels Near Boston

For when the hotel is the destination.

The Red Lion Inn - Stockbridge, MA

• Location: Stockbridge, MA (Approx. 2 hours from Boston)
• Holiday Highlights: This is it—the quintessential New England Christmas hotel. The lobby is legendary, with a massive, beautifully decorated tree, intricate garlands, and cozy fireplaces everywhere.
• On-Site Activities: Kids love finding a spot in the cozy sitting room by the fire or rocking on the front porch, even in the cold. The inn is the centerpiece of the town's holiday magic.
• Dining: The Main Dining Room is a classic New England experience (reservations essential). The Widow Bingham's Tavern is more casual and cozy.
• Why it's Great for Families: It feels like stepping directly into a Norman Rockwell painting (which makes sense, as the museum is right down the street!). It’s pure, old-fashioned holiday magic.

North Conway Grand Hotel - North Conway, NH

• Location: North Conway, NH (Approx. 2.5 hours from Boston)
• Holiday Highlights: If you're heading north for a holiday train ride, this is the perfect family home base. The hotel is close to Settlers Green, which features the "Northern Lights" display, and the hotel itself is decked out in festive decor.
• On-Site Activities: The indoor pool is a massive hit with kids after a cold day of exploring.
• Dining: The Mountainside Restaurant is super family-friendly and has great views.
• Why it's Great for Families: It offers the perfect blend of holiday magic and family-friendly convenience, acting as a warm, cozy base camp for all your White Mountains adventures.

Christmas Towns Worth the Drive

Stockbridge hosts one of New England's most magical Christmas light displays. Photo courtesy of the Trustees

Stockbridge, MA (Approx. 2 hours)

• Signature Decorations: The entire town is the decoration. Famous for being immortalized in Norman Rockwell's "Main Street at Christmas," the town recreates the painting on the first weekend of December (check dates and ticket info, as it’s a major event).
• Top Holiday Events: Winterlights - Naumkeag is a stunning ticketed light show. The Norman Rockwell Museum is a must-visit.
• Santa Visits: Santa is often found at the Red Lion Inn or strolling the famous Main Street.
• Best Places to Eat with Kids: Main Street Cafe offers casual sandwiches and soups.

Kennebunkport, ME (Approx. 1.5 hours)

• Signature Decorations: Home to the world-famous Christmas Prelude, an 11-day extravaganza. Dock Square is the epicenter, with a giant, beautifully lit tree and shops dripping in lights.
• Top Holiday Events: You cannot miss Santa arriving by lobster boat! The Hat Parade, caroling, and sleigh rides are also highlights.
• Santa Visits: He's the star of the show, arriving by sea and greeting kids in town.
• Best Places to Eat with Kids: Alisson's Restaurant is a cozy, family-friendly spot right in Dock Square.

See what a Christmas "cottage" looks like with a holiday trip to Newport, Rhode Island.

Newport, RI (Approx. 1.5 hours)

• Signature Decorations: See how the Gilded Age titans celebrated Christmas. The Newport Mansions (The Breakers, Marble House, and The Elms) are unbelievably decorated with hundreds of poinsettias, giant trees, and elegant lights.
• Top Holiday Events: Christmas at the Breakers is the classic daytime tour. Don't miss Sparkling Lights at The Breakers, an outdoor evening light show. The Bowen's Wharf tree lighting is also a magical night.
• Santa Visits: Santa often makes an appearance at the Bowen's Wharf lighting.
• Best Places to Eat with Kids: Brick Alley Pub & Restaurant is a Newport classic—it's loud, fun, has a great salad bar, and is very kid-friendly.

North Conway, NH (Approx. 2.5 hours)

• Signature Decorations: This is the ultimate holiday train town. The Conway Scenic Railroad station is festive and old-fashioned, and nearby Settlers Green has thousands of lights.
• Top Holiday Events: The #1 must-do is the Journey to the North Pole on the Conway Scenic Railroad. You must book tickets for this the moment they go on sale (often in the summer!).
• Santa Visits: He's the main event on the Journey to the North Pole train ride.
• Best Places to Eat with Kids: Muddy Moose Restaurant & Pub is a local legend, with a fun, rustic atmosphere that kids love. Flatbread Company is another easy, delicious choice.

Old Sturbridge Village (Sturbridge, MA) (Approx. 1 hour)

• Signature Decorations: This isn't a town, but a living history museum that recreates a 19th-century New England Christmas. Think simple, rustic, and incredibly cozy.
• Top Holiday Events: Christmas by Candlelight is the premier event. This ticketed evening experience features sleigh rides (weather permitting), gingerbread baking, carolers, and the entire village lit by candlelight.
• Santa Visits: You'll find a traditional, 19th-century-style Father Christmas.
• Best Places to Eat with Kids: The Bullard Tavern right on-site serves classic New England fare in a historical setting.

Only an hour from Boston, Portsmouth has holidaty fun and plenty of Christmas activities.

Portsmouth, NH (Approx. 1 hour)

• Signature Decorations: A historic, brick-lined seaport with a European feel. Market Square is the festive center, with a giant tree and beautifully decorated storefronts.
• Top Holiday Events: The Candlelight Stroll at Strawbery Banke is a must-do, offering a candle-lit walk through 300+ years of holiday traditions, complete with ice skating and carolers. There is also “A Vintage Christmas” for those interested in seeing how the holiday was celebrated in days of old.
• Santa Visits: He's often at the Candlelight Stroll.
• Best Places to Eat with Kids: Popovers on the Square is perfect for a warm drink and a (you guessed it) popover.

Newburyport, MA (Approx. 45 mins)

• Signature Decorations: A charming coastal town with classic New England architecture. Market Square has a giant tree, and the brick sidewalks are perfect for strolling.
• Top Holiday Events: The town hosts Holiday "Invitation Nights" (check dates) where shops stay open late.
• Santa Visits: Santa's Workshop is set up right in Market Square on weekends!
• Best Places to Eat with Kids: Michael’s Harborside is a fun, local favorite that has lots of fresh seafood and a lovely view of the water.

Rockport, MA (Approx. 1 hour)

• Signature Decorations: A quintessential, artistic seaside village. The main attraction is the unique Lobster Trap Christmas Tree on Bearskin Neck, set against the backdrop of the famed Motif No. 1.
• Top Holiday Events: "Christmas in Rockport" features caroling, Santa's arrival, and the tree lighting. You can also witness a nativity play that parades right through the village!
• Santa Visits: He arrives in true Rockport style—by lobster boat!
• Best Places to Eat with Kids: Roy Moore Lobster Co. is a classic (if open) for a no-frills bite, or head to My Place by the Sea to take in dinner with a view (a little fancier but worth it!).

Ogunquit, ME (Approx. 1 hour 15 mins)

• Signature Decorations: This "beautiful place by the sea" sparkles for the holidays.
• Top Holiday Events: The Christmas by the Sea festival is the main event (check dates, usually early/mid-December). It features a parade, a bonfire on the beach, caroling, and a chowder fest.
• Santa Visits: He's the star of the parade.
• Best Places to Eat with Kids: The Omelette Factory for a great, family-friendly breakfast to start your day.

New England truly shows off during the holidays, and these towns are waiting to be part of your family's story. Whether you're planning a sleigh ride in Sturbridge, watching Santa arrive by lobster boat, or cozying up by the fire in a grand hotel, the important part is just going. Find the spot that sparks that holiday feeling, send this to a friend to start the planning, and book your tickets or hotel. You might just be starting your new favorite family tradition.

All photos courtesy of the author unless otherwise noted.