16 Uniquely New England Holiday Events

16 New England Christmas Holiday Events

1. Winterfest and the Tunnel of Lights in Connecticut

2. Northern Lights Express in Connecticut

3. Winter Solstice Celebration in Vermont

4. Main Street at Christmas in Massachusetts

5. Foundry Artists Association Holiday Show in Rhode Island

6. Mills Falls Marketplace in New Hampshire

7. Christmas Holiday Celebration Inn at Thorn Hill & Spa in New Hampshire

8. Kennebunkport Christmas Prelude in Maine

9. Winter Wassail Weekend in Vermont

10. Christmas at the Nonantum Resort in Maine

11. Weekends at The Lord Jeffery Inn in Massachusetts

12. Santa Brunch at the Beechwood Hotel in Massachusetts

13. Christmas on the Hill in Rhode Island

14. A New England Christmas at Interlaken in Connecticut

15. Christmas by the Sea in Maine

16. Annual Tree Lighting at Water’s Edge in Maine

Unique Holiday Vacation Ideas - Where to Stay

• Connecticut Lodging
• Maine Lodging
• Massachusetts Lodging
• New Hampshire Lodging
• Rhode Island Lodging
• Vermont Lodging

Connecticut: A fun, festive activity for families and children alike, the Winterfest at the Connecticut Trolley Museum features a trolley ride and lots of Christmas carols. Choose from a closed car to avoid the cold, or the open electric sleigh. The Tunnel of Lights is a sight to see! In addition to the trolley ride, the museum itself is a winter wonderland during the season, with lots of decorations, holiday snacks and, of course, Santa Claus. Admission is only a few dollars per person and Winterfest takes place each weekend in December and is one of the most unique Christmas events in Connecticut.

Connecticut: Keeping with the theme of Christmas trains, and not even traveling that far away for the second experience on our list, the Northern Lights Express takes off from the Railroad Museum of New England in Thomaston, Connecticut. Journey to Santa’s workshop and maybe even spot the big guy himself during the ride. The expedition commences each weekend between Thanksgiving and Christmas Eve. The train is filled with decorations and, if you reserve first-class service, you’ll receive a longer visit with Santa, a hand-delivered gift, hot chocolate service and an additional visit with Mrs. Claus and the elves.

Vermont: At Smugglers’ Notch Resort, enjoy a Winter Solstice Celebration Dec. 21. The longest night of the year is welcomed in high style, starting at 3 p.m., with a variety of fun activities. It all kicks off with a winter carnival, then a performance by Cirque De Fuego, the regional premier fire performers, and Burlington Taiko. Along with the live music, there’ll be a bonfire with plenty of s’mores, hot chocolate and apple cider to go around. The evening ends at 8 p.m. with a torchlight parade and fireworks display.

Massachusetts: If it’s an all-American holiday you’re craving, Stockbridge, Massachusetts delivers. Main Street at Christmas channels Norman Rockwell’s famous paintings, which depicted, yes, Stockbridge’s Main Street during the holiday season. You can expect holiday house tours, horse-drawn sleigh rides, visits from Santa, holiday concerts, caroling and more. The celebration takes place Nov. 30–Dec. 2, so you’ll want to make plans now to not miss this iconic event filled with plenty of classic Americana.  This is a classic New England holiday event.

Rhode Island: If you still haven’t wrapped up all your Christmas shopping, or if you have those few people on your list who are just difficult to buy for, make a trip to Pawtucket, Rhode Island, for the Foundry Artists Association Holiday Show, Nov. 29–Dec. 2 and Dec. 7–9.  Unique regional artists come together to display their wares. Admission to the show is free, but you’re encouraged to bring a canned item to benefit the local community. A silent auction also takes place, this year benefiting Friends Way, the only family bereavement center in Rhode Island.

New Hampshire: On Dec. 2, Mills Falls at the Lake in New Hampshire hosts the Mills Falls holiday marketplace, 12–4 p.m. Beyond the wonderful holiday shopping, expect horse-drawn wagon rides, a visit from Santa and strolling carolers. You can even enter to win a $500 holiday shopping spree, perfect for helping out with a little of your gift-giving. Holiday refreshments will also be provided, so you’re sure to stay cozy and warm.

New Hampshire: If you want to actually get away for the holiday itself, maybe get out of town to avoid the inevitable hustle, bustle, stress and drama that sometimes accompanies the big day, the Inn at Thorn Hill & Spa is ready to welcome you to its annual Christmas holiday celebration. Stay over Christmas Eve and Christmas to enjoy some private, guest-only dining where you’re treated like family (or maybe even better than family!). You can also enjoy some live music courtesy of the house band, complimentary Champagne and even a surprise gift. This is a great New England vacation idea for the holidays!

Maine: Kick off the holiday season in seaside style, when you visit Kennebunkport for its annual Kennebunkport Christmas Prelude, Nov. 29–Dec. 9. The full week of fun includes the arrival of Santa by lobster boat, lots of chances to fill your tummy with delicious regional fare, candlelight caroling, loads of Christmas lights, concerts and an arts and crafts show.

Vermont: Show up for Winter Wassail Weekend in Woodstock, Vermont, Dec. 7–9, to celebrate the holidays with a parade of more than 50 horses and riders sporting unique costumes and period dress. In addition to the entertaining parade, you can enjoy holiday concerts, a Wassail Feast, house tours and family-friendly activities that are sure to keep the kids busy (like breakfast with Santa and children’s Christmas book readings). The local shopping outlets also stay open late, so you can pick up that last-minute gift or two.

Maine: There’s certainly no shortage of Christmas events when you stay at the Nonantum Resort in Kennebunkport. Enjoy Christmas concerts performed by the Kennebunkport Consolidated Chorus, both Dec. 1 and 8. Stop by for breakfast with Mrs. Claus and the Elves on Dec. 2, then for breakfast with Santa and Mrs. Claus on Dec. 9. Also Dec. 2, Nonantum Resort hosts a Merry Tuba Christmas, a Christmas concert performed by a tuba choir. Then, Dec. 3–6, get your fill of Christmas cookies with the Cookie Crawl, which starts at Nonantum Resort and continues on to local inns, shops and galleries.

Massachusetts: Every December weekend is a holiday delight at The Lord Jeffery Inn. Each Friday, enjoy live holiday jazz, 6–9 p.m., along with specialty craft cocktails and seasonal menu specialties. Saturday, attend a holiday tea in the cozy library, accompanied by a classical harpist, with festive cocktails. End the holiday weekend the right way with Sunday brunch with Santa. It all makes for a relaxing and stress-free few days as you count down to Christmas.

Massachusetts: The Beechwood Hotel serves up arguably one of the best brunches in the region. The award-winning spread features a special guest Dec. 2, when Santa comes to visit. While children 12 and under enjoy the festivities, the parents can try out the decadent buffet of chef-created specialties and culinary creations, along with a Bloody Mary or Mimosa.

Rhode Island: Celebrate Christmas Day in luxury at Castle Hill Inn in Newport, Rhode Island. The inn is decked out in stylish Christmas decor, perfect to admire from your seat by the fireplace, where you sip some eggnog or munch on another seasonal treat. Upon your arrival, you’ll also receive some festive welcome amenities and you’ll be sent home with a commemorative ornament (though you won’t have any trouble at all remembering such a spectacular holiday spent at Castle Hill!).

Connecticut: Escape to beautiful Lakeville, Connecticut, for Christmas Day, when you stay at Interlaken Inn for a relaxing holiday retreat. A perfect getaway for couples, you have a New England Christmas breakfast for two to look forward to, as well as a traditional Christmas Day dinner, including all your holiday favorites, from prime rib to figgy pudding, to cognac eggnog. All you have to do is show up hungry — no grocery shopping, ingredient prep, hours over the stove or dishes to be washed for this holiday feast! What could be better than that?

Maine: In Ogunquit, Maine, Christmas by the Sea is an annual town-wide celebration with a tree lighting, Christmas parade, beach bonfire, polar plunge…the list goes on and on! Stay Dec. 7–9 and you’re sure to fill every minute of your itinerary with holiday fun. All weekend, you can take advantage of open houses at various shops, for hot cider and cookies while you browse. Then, throughout the weekend, plan your stops at various tree lightings, Christmas parties, caroling concerts and more.

Connecticut: Water’s Edge Resort and Spa hosts a family-friendly tree lighting celebration each year, open to the public at no charge. Admire the beautiful Christmas tree before getting your photo taken with Santa and decorating some yummy Christmas cookies. Keep warm with complimentary hot cocoa and coffee. This year’s tree lighting takes place Dec. 1, 4:30-6 p.m.