Yes, folks, it’s that time again. Whether the season brings you joy or brings you dread, it’s an unstoppable force for all senses. The incessant Christmas tunes on the radio (some of which have been broadcasting since November 1), the ever-present store displays, and the twinkling lights all signal that it’s time for the holidays. For children, of course, this is simply the most exciting event of the year! For adults though, sometimes holiday headaches abound (cue this Christmas classic). This truly is a magical time of the year. That’s why in between elbowing your way through Target and running back to the post office because you ran out of stamps, try to savor some special moments this holiday season. That’s why I bring you “A Very Merry Backyard Road Trips Christmas.”
For 2023- Thanksgiving is on the earlier side which means more events for the Christmas season are actually happening in November this year.
We’ll be exploring my favorite Christmasy New England events, locales, and attractions. From Maine to Connecticut, we’ll touch all six states with places ranging from the touristy to the offbeat. Note: these days it’s almost as if each town with a center has its own Christmas celebration. So by no means is this a comprehensive list. It’s simply a list of events that I can personally recommend. It is divided between specific dates they take place in 2019 followed by ones that are ongoing.
Let the Very Merry Backyard Road Trips Christmas begin!
November 22- December 8
Macy’s annual Christmas Tree Lighting – Boston- Wednesday, November 22, 5-7 pm- Downtown Crossing (Summer Street at Washington Street)
This event kicks off during the day with children’s activities, but the tree lighting event gets underway at 5. This event features well known musical acts (this year it is Natasha Bedingfield) and, of course, a visit from Santa, as the large tree is lit on the top of the store’s awning.
Mystic Boat Parade– Mystic, CT – Saturday, November, 25 at 6 pm in downtown Mystic (Main Street)
Cheer on boats illuminated by Christmas lights and decked out festively for the season as they cruise up the Mystic River through town. While you’re in town, check out the beautifully decorated shops lining Main Street. Also in town, Olde Mistick Village is stunning for the season. A night stroll through here really feels like a walk back in time.
Copley Tree Lighting – Boston, MA – Monday, November 27 at 5 pm Copley Square (Boylston Street) at 5 pm
This fun small event is capped by a beautiful tree being lit in the square. It’s sponsored by the Fairmont Copley Plaza Hotel.
This weekend is the most event-heavy of the very merry Backyard Road Trips Christmas-y season.
Boston Common Tree Lighting – Boston, MA – Thursday, November 30 at 6 pm at Boston Common (off of Tremont Street)
This is the king of the Boston Lighting events (also including the two above lightings as well as Fanueil Hall, Columbus Park Trellis, and Prudential Center lighting ceremonies). It’s widely attended, with national entertainment. This year the headliner is singer-songwriter, Matt Nathanson. Past performers include Jon Secada and Joey and Jordan from New Kids on the Block. The Boston Common is a magical backdrop for this event as vendors sell hot chocolate, and skaters try their luck at wedging their way onto the Frog Pond ice skating rink.
Wickford Festival of Lights – Wickford, RI- Thursday, Nov 30 to Sunday, December 4 in downtown Wickford
Wickford is a quintessential New England town. In its small downtown, colonial architecture is interspersed among independent boutiques. Of course, its waterside location makes it even more charming. Their four-day seasonal stroll features shops that are open later and like many seaside locales, Santa arrives here on a boat!
Christmas in the Square– Hingham, MA – Friday, December 1, 5 – 8 pm downtown Hingham (North Street)
It seems as if the whole town comes out for this popular event! Santa arrives via firetruck in Hingham for a special event that has become a South Shore specialty for over 35 years. The shops stay open too, so “shopping small” is easy to do. There are plenty of fun activities for the kids such as Christmas carols and candy canes.
Light Up City Hall and Winterfest Parade – Norwich, CT- Light Up City Hall – Friday, December 1 at 6 pm (Broadway), Winterfest Parade, Saturday, December 3 at 1 pm
The season comes to the city of Norwich in grand style each year. In coordination with the monthly First Friday events, Norwich’s phenomenal circa 1870 City Hall is outlined with electric lights. Santa flips the switch as the building is lit. Expect family entertainment such as magicians, Christmas carolers, and holiday cheer. The next day is the annual Winterfest Parade. Norwich area businesses sponsor floats as they roll down Washington Street from Chelsea Parade to downtown Norwich. Expect decorated fire trucks, floats, and classic cars and of course, fun for all.
Kiwanis Plymouth Christmas Tree Lighting and Winter Light Road Race – Plymouth, MA- Friday, December 1 from 5:30 pm to 8:30 pm (Town Square)
Santa arrives on a fire truck to light the tree in the middle of Town Square. The festive event includes tractor-pulled hayrides, decorated storefronts, concerts, and events in the churches at Town Square. Santa visits children at the Plymouth Center for the Arts on North Street. Soon after the tree is lit, the annual Winter Light 5K road race begins as the street clears for runners braving the cold December night. Also, there is a luminaria display at the Jenney Grist Mill from 6:30 to 7:30 pm that evening.
Holidays in the Harbor – Scituate, MA – Friday, December 1 from 4 to 8 pm (Front Street)
Get your Christmas shopping done for everyone on your list at all of the unique and varied boutiques that line Scituate Harbor. As part of their First Friday night events, expect mulled wine, hot chocolate, and candlelight illuminating the way, and of course plenty of holiday cheer and music from the businesses.
Holidays on the Green – Plymouth, MA (The Pinehills) – Saturday, December 2 from 11 am to 4 pm (Summerhouse Drive)
The annual Holidays on the Green in the main square of the Pinehills community (Plymouth, MA) is quite simply fun. Santa’s around and visits kids at the post office. The stores are open for business, carolers sing, and food trucks are on-site. There is plenty of family fun such as roasting marshmallows, and wait for it, a Reindog Parade. This is a must-see! At 3 pm watch as herds of mutts strut their stuff wearing their festive best. Each dog is announced as each costume tries to outdo the next. It’s a hoot! The tree lighting is at 4 pm. Look for a petting zoo and characters such as Frosty the Snowman to make an appearance.
Santa’s Arrival by Boat and Tree Lighting – Rockport, MA- Saturday, December 2 from 1 pm to 5 pm (Dock Square)
Another truly classic New England event. Rockport, the quaint seaside town in the North Shore of Massachusetts, is magical at any time of the year. Couple it with festive decorations and Christmas caroling and it’s unmatched. Santa arrives at the harbor on boat. From there he hops a firetruck as it leads to the tree lighting down Bearskin Neck. Another spot to do Christmas shopping at independent stores, Rockport’s event is just an excuse to visit this picture-postcard town.
Portsmouth Holiday Parade – Portsmouth, NH- Saturday, December 2 from 6 pm to 8 pm (Islington/Congress Streets)
This extensive parade travels down Islington and Congress streets before turning right onto Pleasant. The Christmas Tree, located in Market Square, is also lit this evening, starting at 5:20 pm. Talk about Christmas shopping! Portsmouth is the perfect place to pick up something for everyone on your list. The rows of boutiques make it easy to find stocking stuffers for even the most finicky friend.
December 12-15
Although there are only three major events on this list, they are biggies!
Wassail Weekend – Woodstock, VT – Friday, December 8 to Sunday, the 10, 10:00 am to 7:30 pm (Center and Elm Streets)
Maybe this event would be the most likely to represent the quintessential New England Christmastime event? It’s so tough to choose! Whether it does or not, make sure to head up north for this weekend, at least once. Woodstock is all the finest elements of Vermont (mountains, small-town charm, independent businesses, good food and drink) all wrapped up together. This is a whole town affair as all of the stores partake in the celebration. There are demonstrations all over such as at the Billings Farm Museum. On Saturday, a parade winds its way through the center of town and features equestrian riders, floats, and of course, Santa. The tree is lit on the town green and yummy cider, cocoa, and mulled wine abound.
Christmas in Edgartown – Edgartown, MA (Martha’s Vineyard)- Thursday, December 7 to Sunday the 10th (Main Street, etc)
Or could this be the most fantastic event? Similar to Woodstock, this is a multi-day affair. It includes a parade, Santa, great shopping at the local boutiques (with some fantastic sales too), and a tree lighting. One of the favorite traditions here though, would be the annual chowder fest! (I’ve always thought it was a better idea to have a chowder fest in colder weather rather than in the hot summer anyway). There is plenty to do in this fabulous island town. Christmas carols are heard on high and the whole village becomes a holiday-wonderland. At night, strolling through the side streets of Edgartown is magical, as twinkling lights illuminate the buildings and Auld Lang Syne is heard in a speaker of a nearby house.
Holiday Pops! – The Plymouth Philharmonic – Plymouth, MA Saturday, December 9 at 3 and 7:30 pm and on Sunday at 3 pm Memorial Hall (Court Street)
You don’t need to drive into Boston for a breathtaking performance of Christmas Orchestral Pops. The Plymouth Phil, under the direction of conductor, Steven Karidoyanes, offers a delightful program of holiday theme favorites and lesser-known pieces. The selections change annually.
December 16
Kingston Luminaries – Kingston, MA – Saturday the 19th, 5:30 to 8 pm (Main Street)
The Luminaries is the opposite of the pomp and circumstance and the hectic pace the megamall. It is truly a community event. The roads are blocked from vehicular traffic and luminaria line both sides of the road throughout the historic section of town. There are cookies at the former (now a museum) firehouse, a concert, and activities for kids at the community center and a festival of trees put on by the Boy Scouts.
Ongoing Christmasy Themed Events and Places
Cape Codder Resort Enchanted Village – Hyannis, MA – month of December, ongoing.
This Cape Cod hotel mainstay is awash in holiday lights throughout the month of December. Wander through the corridors and into the courtyard to see wonderful illuminated lights that are seemingly everywhere. On Friday, Saturday, and Sunday nights kids can meet Santa, cookies are available to purchase, and carolers greet visitors with the sounds of the holiday. Make sure to take a look at the elaborate train set in the lobby. (free)
Heritage Museum and Gardens- Gardens Aglow – Sandwich, MA, weekend evenings, November 24 to December 23.
Heritage Museum is outstanding when it is open for the season, heck we even added it to our Upper Cape itinerary earlier in the year. For the holidays though, it’s breathtaking. Sit on Santa’s lap in an antique car at the auto museum. There is mulled wine, along with marshmallows to roast in the outdoor cafe. The windmill is illuminated by lights. As you walk through the grounds, the gardens are literally aglow, as trellises are bedecked in twinkling lights. The special exhibit hall features a working toy train and a gingerbread house competition (and the carousel is open for riders in the art museum). (Admission) *these tickets are selling out fast!
Strawberry Banke Candlelight Stroll – Portsmouth, NH – Saturdays and Sundays, December 2 to the 17nd
The living history museum of Strawberry Banke comes alive for the season as visitors can walk the grounds and peek in and out of the buildings as they are decorated for a historic trip through holiday celebrations. (Admission)
Boston Ballet’s The Nutcracker – Boston, MA, Boston Opera House, Tremont Street. November 24 through December 31
Tchaikovsky’s The Nutcracker comes to life like never before on the annual Boston stage. The world-renowned Boston Ballet’s theatrics with the timeless musical accompaniment is something you won’t forget. (Tickets needed)
Blink! – Fanueil Hall Marketplace – Boston, MA – Faneuil Hall. December, 4:30 to 10 nightly.
Be astounded by the sites and sound of the season as the marketplace is awash in holiday lights. The performances run every half hour during the season with the official tree lighting ceremony taking place on December 3 at 7:30. (Free)
Olde Sturbridge Village Christmas by Candlelight– Sturbridge, MA. Fridays through Sunday evenings – November 24 to December 30,. 3 to 8 pm.
Take a stroll back in time where Olde Sturbridge Village becomes a view into a historic holiday. Listen to music, explore the buildings and take a ride in a horse-drawn sleigh as the living history museum becomes a can’t-miss holiday excursion. (Admission)
Mystic Seaport Lantern Light Tours – Mystic, CT – Mystic Seaport, Greenmanville Rd, Mystic, CT. weekends, December 8 to December 23, 5 to 10 pm
Celebrating its th anniversary, this historic event is a play that is staged throughout the grounds and buildings of the Seaport museum. Follow the actors, based on Dickens’ A Christmas Carol as you venture back to the 19th century. (Admission, tickets strongly encouraged in advance.)
Hartford Holiday Lights Fantasia – Hartford, CT- nights, Thanksgiving to New Year’s Day, Goodwin Park, Maple Ave.
Drive through Goodwin Park and be amazed at the extensive holiday light displays that won’t help but bring a smile to your face. (Admission)
Enchanted Village – Avon, MA- located inside Jordan’s Furniture, November 10 to January 1. (Stockwell Drive)
Similar to The Christmas Place, one wouldn’t expect a holiday wonderland inside this giant furniture store. The Enchanted Village was once a Christmastime tradition at the Jordan Marsh department store in downtown Boston. After years of being boxed up, Jordan’s Furniture purchased the display and brought it back to life. It’s a walk through a Victorian Christmas village with animatronic figures of children in street and home scenes. (free)
Edaville Festival of Lights – Carver, MA – November 9 to December 31, evenings-Thursday-Sunday. (Pine Street)
The family-favorite fun park, home of Thomas Land and Dino Land comes to life during the holidays with this annual tradition. The Victorian village houses Santa and there are Christmas displays around every corner. Christmas music is heard overhead and the train ride around the perimeter of the property views all of the magical displays of the property. Best of all, all the rides are running (except Dino Land). Kids truly find this event special!
Christmas at the Newport Mansions – Newport, RI, November 17 to December 30 (Bellevue Ave)
The spectacular Breakers, Marble House, and Elms are all open for tours during the holiday season. Of course, these mansions are astounding all year round, but something about seeing them decked out in complete holiday garb just makes the experience that much more special.
Other A Very Merry Backyard Road Trips Christmas-y Stuff
The holiday spirit can find you wherever you are, even without leaving the house. Putting up the Christmas tree, a fire in the fireplace, a city street stroll, these are just some examples. One of my favorite seasonal activities is taking Christmas light rides. In Connecticut, the Amarante Christmas Wonderland in Dayville is worth a visit and in Massachusetts, Pembroke’s light display on Lilah Lane, where the whole road takes part is truly outstanding. Additionally, visiting a classic inn such as the Grand Victorian Inn in Bethel, Maine or the Quechee Inn at Marshland Farm in Quechee, Vermont, is a perfect holiday getaway for a very merry Backyard Road Trips Christmas.
Of course, these are just a few suggestions for wonderful seasonal events in New England. Whatever you do this holiday season, whatever you celebrate, enjoy yourself and have a truly happy holiday.
PS
Recommended Christmas Viewing: In a time where there are so many new made for television (or pick your streaming service) Christmas “classics,” there are a few annual programs that are a must for me. One, of course, is A Charlie Brown Christmas and I do love National Lampoon’s Christmas Vacation and The Christmas Story. A few of my favorites include the Will Vinton Claymation Christmas and Rick Steves’ European Christmas. To me, both of these really capture the essence of the holiday in very different ways.
