New England Holiday Getaways: Make Your Spirits Bright This Season

Twinkling lights, wreaths with big bows, lazy snowflakes and warm candles glowing in windows are what most of us think of when it comes to the holidays in New England.

And why not?

Of all the places to visit this time of year, none compares with the Northeast’s charming villages and towns, many of which are decked out for the season and offer tidings of holiday cheer.

Some of the best spots to hear sleigh bells jingling and merry bells ringing are only a road trip away. So grab a to-go cup for your eggnog and head to one of these holiday destinations; all guaranteed to make your spirits bright.

Kennebunkport, Maine

There’s a reason former President George H.W. Bush calls Kennebunkport home for at least half the year. Situated on the Atlantic, the quaint village with its boutique shops and fishing boats rocking in the harbor is the idyllic seaside destination.

HAL Photography

Photo Courtesy of Nonantum Resort


During the summer, the sleepy town of 3,500 swells to more than 12,000 as tourists arrive in droves for lobster tours and sightseeing.

The real attraction, however, just might be Kennebunkport’s holiday season.

Beginning the week before Thanksgiving, locals, shop owners and volunteers start by decorating the town from end to end. From common areas to the fence posts, Kennebunkport is transformed into a winter wonderland.

Santa Kennebunkport

Photo Bob Dennis


Then during the first two weeks of December the town hosts its annual holiday celebration, Christmas Prelude.

Now in its 35th year, Christmas Prelude is a menagerie of events including tree lightings, carol sings, fireworks and all things merry.

Pooch Parade

Photo Bob Dennis


There’s also the Hat Parade, which each year draws scores of participants wearing festive hats — many of them over the top. And don’t leave the dogs out: The Pooch Parade features costumed canines of every size and variety joining in a four-legged march.

Both parades are open to anyone interested in participating.

Hat Parade

Photo Bob Dennis


In true Kennebunkport fashion, Santa Claus ditches his sleigh and instead comes to town aboard a lobster boat traveling up the Kennebunk River before shifting to a horse-drawn carriage and riding through the streets to greet children.

HAL Photography

Photo Courtesy of Nonantum Resort


For adults there’s Fire & Ice held each year on the back lawn of the Nonantum Resort during the last weekend of Christmas Prelude. Ticketed guests 21 and older are invited to spend an evening enjoying ice sculptures, bonfires, local food, live music and special holiday drinks served from ice bars.

Nantucket, Massachusetts

Located 30 miles off the coast of Massachusetts and designated as a National Historic Landmark, Nantucket has long been a popular summer haunt for vacationers who come for its pristine beaches and old world charm.

But things really heat up on the island when the cold weather arrives.

Holiday festivities begin the day after Thanksgiving with the kickoff of Nantucket Noel.


Photo Courtesy of Nantucket Chamber Of Commerce


Visitors and locals alike gather at the top of Main Street to watch the lighting of more than 100 Christmas trees accompanied by the local high school choir singing carols.

The first weekend in December is Nantucket’s Christmas Stroll; a three-day celebration complete with carolers in Victorian attire, European markets selling baked items and other goods, live entertainment and storefronts decorated to the nines.

Galvin.300.Centre St Shop

Photo Courtesy of Nantucket Chamber Of Commerce

There’s even a magical talking tree on Main Street enchanting children of all ages.

Midway through the weekend, the town crier rings his bell, signaling all to follow him down to the wharf to welcome Santa, who arrives aboard a Coast Guard cutter and then leads a children’s parade through town.

Santa in baot 2

Photo Courtesy of Nantucket Chamber Of Commerce


Home for the Holidays is an event that happens on the third Saturday of December and includes a yuletide craft fair, carolers, live music, visits with Santa and a “Stroll on Inn” event, which offers visitors the opportunity to see some of the island’s most beautiful inns decked out for the holidays.

Galvin.300.Stroll Main Street Snow

Photo Courtesy of Nantucket Chamber Of Commerce


Throughout the month of December, Nantucket’s Whaling Museum hosts its annual Festival of Trees, with trees decorated by community members, organizations and local merchants on display throughout the historic museum.

Woodstock, Vermont

Nestled among the Green Mountains of Windsor County, Woodstock is pretty much the stuff of New England folklore. Covered bridges, quaint shops and cozy inns can all be found within town lines.

When the holidays roll around, however, the already delightful village is outfitted in hundreds of white lights turning it into a holiday haven, especially during Wassail Weekend.

Wassail Weekend

Photo Courtesy of Woodstock Chamber Of Commerce


For the uninitiated, Wassail is a spiced holiday drink and there’s plenty to go around as many of the town’s restaurants and bars create their own variation to serve guests during the annual event.

But it’s not all about booze.

There also are festive activities through the weekend. Among them is a holiday house tour, where guests are invited to wander through some of the town’s historic homes decked out for the season. Docents are on hand to answer questions and some of the houses have local musicians performing.

Woodstock also hosts an annual Horse and Carriage Holiday Parade.


Photo Courtesy of Woodstock Chamber Of Commerce


Like a scene plagiarized from Charles Dickens, participants dressed in 19th-century attire ride a 2-mile loop through town while more than 2,000 spectators look on.

woodstock i

Photo Courtesy of Woodstock Chamber Of Commerce


Once the parade is finished the official yule log is lit, starting a giant bonfire on the town green. Carols are sung to celebrate and volunteers light 400 luminarias on the green along with the town’s Memory Tree, which honors loved ones.

Other activities during the weekend include a Messiah Sing, sleigh or wagon rides (weather dependent) at Billings Farm and Museum, craft shows and live music events.

Portsmouth, New Hampshire

Just a few hours northeast of Connecticut, the historic seaport of Portsmouth is an easy ride and a great place to make a dent in your holiday shopping.

The city has numerous boutiques, and shops and the Kittery Outlets are only 10 minutes away in neighboring Maine.

However, you’ll likely want to stay put and take advantage of Portsmouth’s month-long holiday celebration, Vintage Christmas.


Photo Courtesy of Greater Portsmouth Chamber Of Commerce


Commencing each year with the lighting of the Portsmouth Christmas Tree, the festivities continue with an illuminated night parade that runs down Isington Street and though Market Square.

The Strawbery Banke Museum offers Candlelight Strolls through its 10-acre outdoor history museum where guests can experience how the holidays were celebrated in the days of old.

Decorations, lanterns, carolers, costumed characters and a bonfire all help set up an old-fashioned scene, and there are candles just about everywhere.


Photo Courtesy of Greater Portsmouth Chamber Of Commerce


The Labrie Family Skate at Puddle Dock Pond, an expansive, outdoor ice rink at the museum, is open daily for public skating,  and on Candlelight Stroll weekends, skaters dressed in period attire put on a Currier & Ives-inspired show.


Photo Courtesy of Greater Portsmouth Chamber Of Commerce


An annual gingerbread house contest receives dozens of impressive entries made by local artists, businesses, families and community members, all of which are on display at Discover Portsmouth Center through Dec. 23.

To make getting around a little easier, The city provides free transportation on the weekends (and Dec. 16) via the Vintage Christmas Trolley, as well as free parking the week of Christmas.

Old Saybrook, Ivoryton And Essex, Connecticut

There’s no place like home for the holidays and what better getaway than one that’s in your own backyard?

Picturesque and welcoming, Old Saybrook’s historic buildings and tranquil location on Long Island Sound make it a great place to visit all year long.

But dressed up for the holidays and with so much going on, it will really get you into the spirit.

Old Saybrook’s annual Winter Stroll, on Dec. 2 this year, entices visitors for a night of shopping, refreshments, music, horsedrawn carriage rides and a visit from Santa.


Photo Courtesy of Old Saybrook Chamber Of Commerce


The following weekend the town hosts its long-running Torchlight Parade with an array of costumed drum and fife corps marching down Main Street playing spirited selections from days gone by.

In nearby Ivoryton, Illuminations, the village’s annual holiday light show, gets underway on Dec. 3 with a carol sing, a visit from Santa Claus and the lighting of one of the tallest living Christmas trees in the state.

Ivoryton I

Photo Courtesy of the Ivoryton Playhouse


The show features more than 300,000 lights dancing to music throughout the month of December.

In Essex, the Valley Railroad Company invites guests to climb aboard the Essex Stream Train which offers two holiday events including the Santa Special, a one-hour daytime train ride aboard festively decorated cars and the North Pole Express, a 90-minute nighttime journey with musical performances, sing-alongs, refreshments and a special guest star dressed in red.

Santa w Girl in PJs

Photo Courtesy of the Essex Steam Train


Also in Essex, the historic Griswold Inn continues its long-standing tradition of celebrating the holidays with a special game menu, staff dressed in period costumes and carolers making the rounds to get everyone in the holiday spirit.

Finally, whether you’re in need of trimmings or just some ho-ho-holiday inspiration, you’ll find both at the Pink Sleigh Christmas Shop in neighboring Westbrook.


Photo by Susan Haddad


Housed in an old post-and-beam country barn, the shop is chock full of holiday accoutrements, ornaments and all things Christmas-related. The Pink Sleigh opens its doors in July and wraps up for the season on Christmas Eve.

Originally Published Hartford Magazine November 2016