The Most Charming Christmas towns in New England

New England is a treasure trove of Christmas charm. Of course, if you have followed this blog you know I’m a big fan of two things: New England charm and the holiday spirit. I love the giddy feeling that floats on the chill in the air, welcoming the best in everyone to come out. In my travels, I found that some charming little towns just do. it. right. From parades where Santa comes over to town on a boat to lighthouse tours in the snow storm, I’m running the list of my favorite holiday towns in New England to visit this holiday to get in the spirit.

As you may know, I have been trying to put together a podcast. I wanted to invited creative minds and business mavens to combine two of my favorite things: inspiring each other and travel. A travel guide should be a recommendation from a friend. That’s what I aim to do on my podcast postcards podcast. Taking the friends you all know so well on social media and translate their favorite places to your favorite places. This week, we have Aubrey from the Coastal Confidence. A business maven and blogger, Aubrey runs a blog on travel and style in New England. Her posts are always colorful and charming.

Christmas in Connecticut

To get the full run down on the best Christmas celebrations in CT listen to our first episode below tune in for the secret to:

where to go to see the best Christmas lights

Exclusive can’t miss seasonal events

Where to explore the set of your favorite Hallmark movie

Listen to the Pocket Postcard Episode 1 here!

Christmas in Rhode Island

Newport Holiday Stroll – Newport Dec 7-8, 2019

If you’ve never been to this cozy village by the sea, it is a must see. This year the city is hosting it’s third annual Newport holiday stroll. Along with shopping your heart out at the stores that line the cobbled streets, stop by the Mansions on the cliff walk, live entertainment throughout the city including busking and caroling, and fun for the whole family with ice skating downtown and the Bowen’s Wharf 49th Annual Christmas Tree Lighting with Santa Claus. Don’t forget to grab your cup of clam chowder on the way home!

Christmas in New Hampshire

Nashua Winter Holiday Stroll – Nashua, NH November 30th 

Main street shuts down for caroling pedestrians during this open house style market. Wander into stores sipping hot chocolate. Great for kids and families!

Vintage Christmas – Portsmouth, NH Every weekend in December

Along with a holiday parade, this quaint coastal town is home to a lovely vintage Christmas festival at the Strawbery Banke Museum. The museum, which was a colony 300+ years ago, welcomes visitors to travel along candlelit dirt lanes to walk through a historic portrayal of winter. The magical experience will be accompanied by a full program of musical performances and theatricals.

Inn to Inn Holiday Cookie Tour White Mountains, NH Dec 14-15

Exactly as it sounds, this celebration kicks off with sweet treats baked with love from the bed and breakfasts in the area. Grab a sugary snack and feast on the snow capped mountain views. This self guided tour is great for a weekend with the girls or gran.

Christmas in Maine

Freeport Sparkle Weekend- Dec 6-15, 2019

Freeport lights up for this weekend of family fun. Events feature a Parade of Lights down Main Street, Freeport’s Talking Christmas Tree, Holiday Movie Marathon, A Reading of the The Polar Express aboard the Amtrak Downeaster, Tuba Christmas Concert, Visits with Santa, Horse Drawn Wagon Rides, Musical Holiday Light Shows, a Crooked Playhouse Village, Holiday Ornament & Craft Projects. For a full guide of Freeport see here.

Christmas Prelude, Kennebunkport   1st & 2nd Weekend after Thanksgiving Weekend.

This extravagant Christmas festival is designed to immerse visitors into the North Pole. As you walk around town, shopkeepers welcome you with warm drink, snacks, and festival coastal decor. During this two week event, Christmas carolers sing our favorite jingles, historic houses are open for tours, there are wine tastings, horse drawn wagons, and a hat parade. The two weekends differ slightly: the celebrations officially begin with the Tree Lighting Ceremony on the 1st weekend of Christmas Prelude. During the 2nd weekend, spectators can enjoy the Christmas Fireworks Display and the Pooch Parade (where man’s best friend displays the holiday spirit with Christmas apparel). sounds like a can’t miss!

Festival of Lights, Rockland Nov 29- Dec1, 2019

Come to see the world’s largest Christmas Tree made of Lobster Traps is lit up in this charming coastal town. Join the caroling, horse-drawn carriage rides, warm up by the bonfire, browse the shops, enjoy refreshments. Of course, you don’t miss Santa arriving by boat. See where to stay here 

Christmas in Vermont

Woodstock, Vermont | Winter Wassail Weekend December 7 – 9

The annual Winter Wassail Weekend in Woodstock features a parade with over 50 horse riders outfitted in 19th century costume and dress. Along with unique vintage aesthetics, the celebration offers concerts, a Saturday night Wassail Feast, historic house tours, yule log and activities for children. The shops in town stay open late for all of the names on your list.

Christmas in Massachusetts

Christmas on the Cape – Hyannis November 30-Dec 1

This year will be my first Christmas on the Cape and it is a New England staple! I could not be more excited about the proximity of the charming Hyannis or the family fun that is promised to be offered here. For starters, you can expect to see Santa driving over on a fishing boat in Hyannis Harbor and Special season brews at  at Cape Cod Beer. And let’s not forget the light drive in extravaganza that is Garden’s AGlow! Read the full guide here 

Christmas in Edgartown – Martha’s Vineyard  December 14-15, 2019

Another coastal favorite, Christmas in Edgartown was a truly magical experience for my family and I. From lighthouse lightings to a festive parade with Santa on a jeep – this heartwarming celebration has something for the whole family. To read the full guide, please read my post here.

Nantucket Stroll – Nantucket November 30-Dec 1 

The original Nantucket Christmas Stroll in 1973 was merely trying to prevent islanders from escaping to Cape Cod, 26 miles across the Sound, to do their holiday shopping.”  A great success, now more than four decades later, the stroll continues with fervent awe. Seven foot Christmas trees illuminate your walk as you admire the collections from local shopkeepers. Carolers line the street and you can’t help but feel St Nicholas will soon be there.

Winter Market – City Hall Plaza Boston, MA 

November 24-December 31:
Monday-Thursday’s: 11am-8pm
Friday-Saturday’s: 11am-9pm
Sunday’s: 11am-6pm

Regrettably, as a Boston native I very often overlook the majesty in my own zip code. The past few years the folks down in Faneuil Hall have run a cute little pop-up winter market. Little booths huddle together like arctic penguins, mimicking the festive stalls of Northern Europe. Grab a hot chocolate and skate with your loved ones or littles ones on this cozy rink. It is a great way to spend a festive afternoon.

Christmas in Stockbridge, MA 

This town’s claim to fame is a bring the backdrop for a famous Norman Rockwell painting. So, you know they do a great New England Christmas celebration. Holiday house tours, caroling, horse-drawn rides, a visit with Santa, and concerts make the weekend merry, but it’s tough to top the Sunday afternoon re-creation of Rockwell’s painting, complete with period automobiles.