Four quintessential New England towns welcome Christmas-season visitors
By Telly Halkias
Horse-drawn sleigh rides, carolers, town square Christmas tree lightings, shoppers, arms piled high with packages, bustling through the downtown — the quintessential ingredients of a New England Christmas Town.
At least that’s how renowned illustrator Norman Rockwell captured the essence of the holiday season in New England — a slice of Americana that has fueled the nation’s imagination since its founding.
The essence that he captured, from Thanksgiving right up to Christmas, is that of local communities, residents and visitors alike, bonding in the ambiance, décor, and unity of celebrations meant to bring people together in a season known for its joy and harmony.
Travelers seeking out the warmth, charm and community spirit of Rockwell’s paintings and illustrations need only to look to towns and villages of The Berkshires and Southern Vermont, where the artist lived and worked. In Stockbridge, Mass., visitors can literally step into Rockwell’s painting, “Stockbridge Main Street at Christmas (Home for Christmas),” during the town’s three-day festival of the same name. This year, the 28th annual Stockbridge Main Street at Christmas, will take place Dec. 1-3.
Barbara Zanetti, executive director of the Stockbridge Chamber of Commerce, said residents look forward to this time of year just as much as the throngs of visitors.
“Being right after Thanksgiving, it’s a time to enter the Christmas season with our downtown decorated and welcoming to everyone who visits, and this weekend bring out visitors ,” Zanetti said.
One of the more popular events is the “Holiday Historic House Tour,” which features a selection of the federalist and colonial homes and Gilded Age cottages from Stockbridge, Lenox and Lee. Local historian Carole Owens said this year’s stops were “carefully selected to delight and sometimes to even amaze.”
The highlight of the weekend, taking place that Sunday, is the annual recreation of the painting, “Stockbridge Main Street at Christmas,” which hangs just a few miles down the road in the Norman Rockwell Museum.
The recreation differs a bit from the painting with about 50 instead of 16 antique automobiles, but comes complete with Roger the Jester and all of the painting’s other trappings, including the Red Lion Inn, for a few fun-filled hours.
Follow Route 7 north into Vermont to Arlington and Manchester, where Rockwell lived and worked prior to moving to Stockbridge, to find a historic corridor filled with plenty of winter and holiday delights.
While eight miles apart and each with its distinct feel, both Arlington and Manchester have long joined forces in holiday activities, as Route 7A provides a scenic winter drive experience. There are quaint shops along the way, anchored by – what else – arguably one of the most well-stocked Christmas décor establishments anywhere, Christmas Days, found right between the two villages.
But back to Arlington, the place where Rockwell called home (and you can still see it) and also where he had local citizens sit as models for his now-iconic paintings, many which graced the cover of The Saturday Evening Post.
Arlington is the starting point of a regional celebration, nearly a month of events for locals and visitors called Manchester Merriment, which runs from Nov. 24 to Dec. 31, encompassing even the celebration of New Year’s Eve.
Along with some of the area’s most welcoming people, over two Saturdays, Dec. 2 and 9, visitors are welcome to take on the Historic Inn Christmas Tour.
The tour, which can be entered upon at multiple locations, ideally begins at the regal Arlington Inn, where innkeeper Elizabeth Berger looks forward to it each year.
“We love the holiday inn tours because we get to show off the inside of the inns, and each property is so unique.” she said. “The visitors are in such great spirits, and we often hear them say they are going to try and ‘decorate like that’ at home. It’s such a fabulous way to kick off the holidays, welcoming happy people and knowing that the event [sends] all of the proceeds to the local food shelters.’
The tours are a perennial hit. Visitors can decorate a holiday cookie, enjoy chocolate and wine pairings, sing some holiday tunes with a live pianist, and more. Being self-guided, one can pick somewhere new to go or stay longer at a favorite place.
Manchester Merriment continues to offer up a full slate of events. One of the favorite for kids is the Lighted Tractor Pull in Manchester on Dec. 2. Antique and modern tractors adorned in lights and holiday trimmings make their way down Main Street. Each tractor is uniquely decorated in the spirit of the season and shines bright in the winter evening. And of course, there are more children present having fun than the eye can see.
A final stop in Southern Vermont brings us to Woodstock, where at the start of the Christmas season, the town welcomes visitors during its annual Wassail Weekend.
The event, which runs from Dec. 8-10, begins that Friday with sleigh rides at the Billings Dairy Farm and Museum. The farm will host visitors all day throughout its facilities and offer up sleigh rides across its expanse.
On Saturday, Woodstock puts on its own highly popular version of a Christmas-decorated historic homes tour. Guests can soak up the warmth of old New England, when Woodstock’s most charming houses deck their halls and open their doors.
The tours, which are self-paced and begin at the town hall theater, have docents awaiting at each location to provide historical information and answer questions. Some of the homes feature live performances by local musicians.
After the tours, on Saturday afternoon, is the Wassail Equestrian Parade through the center of Woodstock. More than fifty horses and riders dressed in holiday costumes and period dress from the early 19th century greet well-wishers lining the streets. Santa Claus puts in an appearance and then heads on to Little Theater on River Street, where he continues to entertain the children.
New Englanders like to say there is no place like right here for the holidays. These four quintessential towns, all different in their own ways, have the common thread of hospitality running through them during the Christmas season, and welcome all comers.
If you go…
Stockbridge Main St. at Christmas
Information: stockbridgechamber.org or call 413-298-5200
Friday, Dec. 1
5-6:30 p.m. Readings Around the Hearth
Gather ‘round to hear classic stories of the season at the Stockbridge Library, Museum & Archives. Free Admission.
Saturday, Dec. 2
11-4 p.m. Holiday House Tour
Visit historic homes, inns and private homes in Stockbridge, Lenox and Lee. This self-guided tour stops at Blantyre, Naumkeag, Eastover Resort, The Charles Owen House, Federal House Inn and the Old Rectory. Tickets are $20 each and may be purchased in advance through the Stockbridge Chamber of Commerce or on the day of at the Red Lion Inn. Tickets are not at the house tour stops.
11-11:30 a.m. Children’s Holiday Story Time
Stockbridge Library Museum & Archives. Free Admission.
6-7 p.m. Caroling Luminaria Walk
Meet in front of The Red Lion Inn, Main Street with your candle or flashlight and join the festive caroling, followed by a Luminaria walk to the First Congregational Church.
7:30 p.m. Holiday Concert
Holiday musical program by the Berkshire Lyric and the Blafield Children’s Chorus held at the First Congregational Church. Tickets are $25 each. General admission seating.
Sunday, Dec. 3
Noon – 2 p.m. Stockbridge Main Street at Christmas Recreation
Main Street becomes a magical New England village with over 50 antique cars parked along the street (weather permitting) and a full range of festive activities to delight the child in everyone. Enjoy Roger the Jester and lunch at the Christmas Food Booth. Holiday music by Monument Mountain Regional High School. Create holiday fun at Santa’s workshop sponsored by the Norman Rockwell Museum and visit with Santa.
Commemorative buttons offering admittance to Sunday’s Main Street activities are $5 each. Children under 12 free. Horse drawn wagon rides by Clay Hill Farm will also be available for an additional fee.
Tickets: Purchase in advance through the Stockbridge Chamber of Commerce or in person the week of the events at The Red Lion Inn. Tickets to all events are limited. Advance purchase is strongly suggested as they can sell out.
Saturday, Nov 25
Manchester Tree Lighting
Manchester Merriment kicks off with a visit from Santa and Mrs. Claus at the annual tree lighting ceremony on the Factory Point Green. The festivities begin at sunset. Santa and Mrs. Claus will arrive by fire truck.
Saturday, Dec. 2 and Saturday, Dec. 9
Noon – 4 p.m. Historic Inn Christmas Tour
Starting at the Arlington Inn, the 2017 Historic Inn Christmas Tour will take you to historic, elegant and modern inns and hotels in Manchester and Arlington. Tickets for the self-guided tour come with a map of the participating inns and hotels. Proceeds from ticket sales will benefit area food pantries.
Saturday, Dec. 2
5:30 p.m. 6th annual Lighted Tractor Parade
Bring your favorite lawn chair and watch area non-profit organizations, businesses and townspeople show off their tractors, floats, buses and more as they compete for prizes as they parade through town and light up the night. The parade will be followed by a visit by Santa and Mrs. Claus.
Information: woodstockvt.com or 802-457-3555
Friday, Dec. 8
10-4 p.m. Christmas at the Farm
Visit Billings Farm and Museum, 69 Old River Road , Route 12N & Old River Road, for demonstrations, tours and sleigh rides. More information: billingsfarm.org
5-7 p.m. Woodstock History Center Open House
Take a stroll to the Woodstock History Center, 69 Elm Street, for an open house that includes a tour, holiday music, and light refreshments. More information: woodstockhistorycenter.org
Saturday, Dec. 9
9:30- 2 p.m. 16th Annual House Tour at Woodstock Village
A Wassail Weekend favorite! Experience the warm hospitality of old New England,. Tours are at your own pace. Tours begin in the Woodstock Town Hall Theatre. Tickets: $35 before November 30. $40 for adults, free for children 17 and under. More information: pentanglearts.org/event/house-tour-201
2 p.m. 33rd Annual Equestrian Parade
Watch the parade from the Village Green in the center of town. Coordinated by High Horses Therapeutic Riding Program and the Woodstock Area Chamber of Commerce.
8-10 p.m. Christmas with the Celts at Woodstock Town Hall Theatre
Christmas with the Celts combines fiery new arrangements of modern seasonal classics, including John Lennon’s “Happy Christmas,” with ancient carols. Tickets: $40 for reserved seating for adults; $35 for Pentangle members; $20 for children ages 5-17. More information: pentanglearts.org/event/christmas-with-celts
Sunday, Dec. 10
4-6 p.m. Annual Messiah Sing at Our Lady of the Snows Catholic Church
The annual conclusion to Wassail Weekend. Louis Burkot directs a world-class ensemble and four featured soloists in a stirring rendition of the Christmas portions of Handel’s Messiah. The audience joins in for the choruses, so bring your libretto. Suggested donation of $10. More information: pentanglearts.org/eventmessiah-2017
Telly Halkias is a national award-winning, independent journalist. He lives and writes from his homes in southern Vermont and coastal Maine.