Travel

The most Christmas-y towns in New England

These towns are full of holiday spirit.

By Kristi Palma

November 27, 2023

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New England is brimming with Christmas spirit, and some cities and towns are taking holiday cheer to the next level.

If your goals this season involve spending time in places that feel like a Hallmark holiday movie, the following destinations are certainly up to the task.

Stockbridge, Mass.

Stockbridge, named among the most “magical” Christmas towns in the U.S. by Country Living, invites folks to literally step into a Norman Rockwell painting when the town re-creates the 1967 Rockwell painting “Stockbridge Main Street at Christmas (Home for Christmas)” every December during Stockbridge Main Street at Christmas. Guests enjoy holiday markets, live performances, historic property tours, and more as old-fashioned cars line Main Street. This year’s Stockbridge Main Street at Christmas event takes place Dec. 1-3.

Nantucket, Mass.

Nantucket, well known for summer fun, hosts winter fun in a big way during its annual Christmas Stroll full of special sales and promotions at island stores. Visitors can shop Santa’s Village at the Christmas Stroll Marketplace, sing Christmas carols, shop craft shows, take tours, watch live performances, and view dozens of decorated Christmas Trees lining downtown streets. For even more Christmas trees, head to the Whaling Museum‘s annual Festival of Trees featuring trees decorated by community members. Nantucket was named among the best Christmas towns in the U.S. by Travel + Leisure. The island’s 49th annual Christmas Stroll takes place this year Dec. 1-3.

Essex, Conn.

There is plenty of holiday fun planned this year at the 14th annual Ivoryton Illuminations in Essex, named among the most “magical” Christmas towns in the U.S. by Country Living. The event includes a tree lighting, holiday street market, letters to Santa, petting zoo, elf scavenger hunt, cookie decorating, and more. Also in Essex, families can board the North Pole Express and enjoy sing-a-longs, hot chocolate, and cookies, courtesy of the Essex Steam Train and Riverboat. For overnight trips, consider staying at the historic 1776 Griswold Inn, one of the oldest continuously operated inns in the country. Ivoryton Illuminations festivities take place Dec. 2.

Kennebunkport, Maine

Santa famously arrives by lobster boat every year during Kennebunkport’s annual Christmas Prelude. Before that, visitors can enjoy trolley rides, caroling, a street festival, lobster bakes, crafts, fireworks, and more. Jenna Bush Hager attended last year with her family and said, “I basically stepped into a Hallmark Christmas movie.” Kennebunkport was named one of the best Christmas destinations in America by Conde Nast Traveler and one of the most “magical” winter towns in the U.S. by TripsToDiscover.com. The Christmas Prelude takes place this year from Nov. 30 to Dec. 10.

Woodstock, Vermont

During Woodstock’s annual Wassail Weekend, the town becomes “the ultimate winter wonderland,” wrote Thrillist. Visitors enjoy three days of events that include a parade, carriage rides, artisan markets, film screenings, holiday performances, and a chance to experience 1890s holiday traditions on a working dairy farm. Thrillist named Woodstock a small town with the most holiday cheer in America and Country Living named it among the most “magical” Christmas towns. Wassail Weekend takes place this year Dec. 8-10.

Ogunquit, Maine

Ogunquit was named among the best Christmas towns in America by Travel + Leisure in large part due to its annual Christmas by the Sea festival. The event brings tree lightings, a parade, concerts, craft shows, children’s activities, a bonfire, fireworks, Santa’s arrival, and more. Don’t forget to check out the Harbor Candy Shop on Ogunquit’s Main Street, noted Travel + Leisure, for great stocking stuffers. The Christmas by the Sea festival takes place this year Dec. 8-10.

Newport, R.I.

Wander through elaborately decorated Gilded Age mansions in Newport this holiday season, named among the best Christmas towns in America by Reader’s Digest. The lavishly decorated Elms, Marble House, and The Breakers sport Christmas trees, wreaths, and more. At the latter, folks can view a 15-foot poinsettia “tree” in the Great Hall, made up of 150 poinsettia plants. Outside, tens of thousands of colored lights twinkle across 13 acres during Sparkling Lights at the Breakers. Holidays at the Newport Mansions is ongoing through Dec. 30.

Portsmouth, N.H.

Visitors to Portsmouth experience a Vintage Christmas each year, complete with a holiday lights parade, gingerbread house decorating contest, musical shows, a free Vintage Christmas Trolley, and an elaborately decorated Market Square. Strawbery Banke, a living history museum on the waterfront, features a Candlelight Stroll among decorated historic buildings, hot apple cider, and a bonfire. Portsmouth was named among the best Christmas towns in America by Reader’s Digest. Vintage Christmas takes place throughout the month of December.