Home Spotlight SeriesNew England Places 2019 Best New England Holiday Events for the History Lover

2019 Best New England Holiday Events for the History Lover

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Every year New England offers a host of opportunities to mix holiday cheer with some of the historic flavor of our region, and 2019 is no exception. From carousels to trolleys to historic homes, November and December offer all manner of chances to get you Holiday History on. Here are 13 of our favorites:

New Hampshire

Christmas at the Castle – Moultonborough, N.H.

Castle in the Clouds is the Arts and Crafts style mansion built by Bath, Maine’s Thomas Plant. Plant made his fortune in shoemaking and designed the lavish mountain-top mansion Lucknow. The lavish mansion gets a Christmas facelift and is opened for visitors during the Christmas at the Castle. The event runs weekends in November, and the Castle also hosts a visit from Santa on Dec. 14.

Visitors can also make a weekend of it shopping and dining throughout the Lakes Region.

Where to Stay:

Accommodations include the Inns at Mill Falls in Meredith and the historic Pickering House Inn in Wolfeboro.

Strawbery Banke

Forty years is but a blink of an eye for the village at Strawbery Banke, but that’s how long the outdoor museum has been hosting its annual holiday Candlelight Stroll. This year the event takes place December 7, 8, 14, 15, 21 and 22. Visitors stroll from house to historic house, greeted by costumed role players and performers who recreate the traditions of times past, rediscovering the joys of simpler times.

The stroll is one of the cornerstone events of Portsmouth’s Vintage Christmas in Portsmouth festival.

Where to Stay:

Nearby Accommodations include Ale House Inn, a wonderful selection of Bed & Breakfasts and the historic Wentworth By The Sea.

Rhode Island

Christmas in Newport


The Breakers, decorated for the holidays.

Newport for the past 49 years has celebrated the noncommercial aspect of the holidays with an annual  festival that now stretches through the whole month of December. This year Christmas in Newport features a doorway decoration contest, concerts to benefit local charities, historic walking tours and mansions decked out for the holidays.

This year the Historical Society will take you to an early American Christmas on its Holiday Lantern Tours every Friday and Saturday at 4 p.m. They start on Nov. 22 and end on Dec. 28. Visitors will learn how Newporters did, or did not, observe the holidays during this evocative stroll.

Meanwhile, for visitors more interested in the city’s Gilded Age, the Breakers, Elms and Marble House will be decked out with spectacular holiday decorations. The homes are on Christmas display Nov. 23rd ‘til Jan. 1.

The Newport Preservation Society will decorate Rough Point in the style of its fabulously wealthy owner, Doris Duke. Visitors will be free to roam around the first floor or take a guided tour, or both.

Up the road in Bristol, the Blithewold Estate will be ornately decked out for the annual Christmas at Blithewold running Nov. 26 through Jan. 1.

Accommodations: In Newport you can stay at at least two hotels on the National Register of Historic Places: the 1760 Francis Malbone House, designed by Peter Harrison, one of America’s first architects, or the Newport Bay Club & Hotel, a former textile mill on the National Register of Historic Places. There’s also the quaint – and centrally located – Admiral Weaver Inn.

The Looff Carousel With Santa

In Providence, children can ride the historic Looff Carousel at the Roger Williams Park Zoo & Carousel Village while they wait to visit with Santa. The jolly old elf will be available from 10 a.m. to 3 p.m. from Friday, Nov. 29 to Sunday, Dec. 1. You can also take in a live performance of Charles Dickens’ classic, A Christmas Carol, at the Trinity Rep, from now through Dec. 29.

Accommodations: Providence is full of historic hotels, including the old Providence-Biltmore, now the Graduate, which is on the National Register of Historic Places. You could also stay at the Christopher Dodge House, a bed and breakfast built in 1858, or the Hotel Providence, a landmark in the city’s Downtown Providence Historic District.


Coolidge Presidential Birthplace

The Coolidge Presidential Birthplace in Plymouth, Vt., gets into the holiday spirit by throwing open its doors on Saturday, Dec. 7. Visitors will find the house decorated as it was in 1872, when Calvin was born. The historic complex will also feature sleigh rides, story-telling, chocolate-making and a special stamp cancellation at the post office.

Wassail Weekend


The Woodstock parade.

It’s just down Route 4 from Rutland, Killington and Woodstock, which offers the Woodstock Wassail Weekend Dec. 13-15.  There’ll be music, a holiday tour of houses on the green, yule logs, an artisan market and the 35th annual parade.

Woodstock has many fine lodgings, including the Jackson House Inn, formerly the Wales N. Johnson House listed on the National Register of Historic Places. Other inns, such as The Woodstock Inn & Resort and The Blue Horse Inn, are within Woodstock’s charming historic district.


Christmas at Victoria Mansion

Head to Victoria Mansion in Portland from Nov. 29, 2019 to Jan. 5, 2020 to see how local artists, florists and designers decorated the mansion’s 19th-century interiors. Also known as the Morse-Libby Mansion, the landmark building shows what lavish living was like in 19th century America.

Accommodations: Portland has several charming Victorian-era hotels, including the Inn at St. John, The Francis and the Inn at Park Spring.

Christmas Prelude

Since 1982, Kennebunkport has held Christmas Prelude events, which now stretch from Dec. 5-15 and include historic house tours. The Kennebunkport Historical Society kicks off the two-week gala with a reception at the 1853 White Columns house. White Columns is later open for tours, and the Seashore Trolley Museum offers rides in a heated streetcar through the Maine woods.  Then on Dec. 11, Kennebunkport holds candlelight tours of the town’s historic inns. You can stay at them too. They include the Captain Lord Mansion, the Captain Jefferds Inn and the 1802 House Bed & Breakfast.


Black Nativity

Boston’s captivating production is the longest running performance of Harlem Renaissance poet Langston Hughes’ song-play in the world. The show, in its 49th season, runs from Dec. 6 to Dec. 22 at the Emerson Paramount Center.

Accommodations: The Parker House Hotel, now the Omni Parker House, has been lodging guests – including Charles Dickens — on the same site since 1855. The luxurious Liberty Hotel has been transformed from the historic Charles Street Jail, built in 1851 and emptied of prisoners in 1990.

Christmas By Candlelight

Sturbridge Village, a recreated 19th century New England Village, holds its annual Christmas By Candlelight celebration on Dec. 6-8, Dec. 13-15, Dec. 20-23 and Dec. 27-29. The event features a roaring bonfire, sleigh rides, live musical performances and holiday traditions such as roasting chestnuts, yule logs, mistletoe and demonstrations of period holiday baking and cider mulling.

Accommodations: You can stay in Sturbridge Village itself at the Old Sturbridge Inn and Reeder Family Lodge or in Sturbridge at the Publick House Historic Inn and Country Motor Lodge.

Christmas in Salem

The seaport city of Salem celebrates Christmas over three days with a candlelight stroll, a concert and a tour of richly decorated – and historic — houses in the Upper McIntire. Historic Salem, Inc., sponsors the 40th annual event, which will run from Dec. 6-8.

Accommodations: Salem offers several historic hotels, including the Hawthorne House and the Salem Inn, and the Marblehead Inn in Marblehead, the next town over.




A table set for the holidays at the Joseph Webb House.

The Webb-Deane-Stevens Museum will hold its annual “Three Centuries of Christmas Tours” on weekends: Saturday, Dec. 7, 10 a.m. to 4 p.m., through Sunday, Dec. 29, 1 to 4 p.m. Admission is $12. The Silas Deane House will showcase an 18th-century New Year’s Day Calling, since the Puritans didn’t hold with Christmas. The Isaac Stevens House will depict holiday celebrations of a middle-class household during the early to mid-1800s. Finally, the Joseph Webb House will show decorations typical of the early 20th century. Tickets are $12.

Accommodations: You can stay in one of two bed & breakfasts located right in the Old Wethersfield Historic District: The Silas W. Robbins House and the Chester Bulkley House.

Mystic Seaport Museum

The 40th anniversary of the Mystic Seaport’s Lantern Light Tours will feature a new spin on Dickens’ A Christmas Carol. Tourgoers will be treated to a 70-minute traveling play in which Mallory’s Ghost tries to save his partner and Greenmanville from becoming an expanse of deserted shipyards. Performances run from 5-8:30 p.m. on Nov. 23, 29, Dec. 6 and from 5-10 p.m. on Nov. 30, Dec. 7, 13-15, 20-22.

Accommodations: In downtown Mystic, the Whaler’s Inn has been hosting guests for 125 years, and the nearby Spicer Mansion, which dates to 1853, recently opened to guests.

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