Tis the Season for some holiday fun! From sparkling lights to festive markets and window displays, there’s something undeniably magical about the holidays in New England.
To help you add a little sparkle to the season I’ve put together this holiday bucket list! Try one or all to celebrate the season.
- Tour a Decked Out Castle
- Visit a Giant Gingerbread Display
- Enjoy a Festive Drink
- Have a Little Wine with Your Winter Lights
- Explore the SoWa Winter Market
- Celebrate Vintage Christmas in Portsmouth, NH
- Visit a Festival of Trees
- Experience Kennebunkport’s Christmas Prelude
- See a Lighthouse All Dressed Up
- Attend a Classic Holiday Show
- Get Creative with DIY Gifts
- Volunteer or Donate Locally
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Tour a Decked Out Castle
One of my favorite ways to get into the holiday spirit is by touring a historic mansion decked out for the season. There’s something magical about seeing these historic homes decorated with twinkling lights and festive decor.
The Newport mansions may be famous for their holiday displays, but Hammond Castle, in Gloucester, MA, offers a unique twist when it comes to dressed up homes.
Built between 1926 and 1929, this medieval-style castle is situated on the edge of a steep bluff overlooking the Atlantic Ocean. It was home to inventor John Hays Hammond Jr. and is rumored to be haunted.
During its annual Deck the Halls event, Hammond Castle transforms into a festive wonderland with each room filled with holiday decor and twinkling lights.
Add an evening candlelight tour to see the castle’s holiday decor glowing in soft candlelight.
Hammond Castle (80 Hesperus Ave, Gloucester, MA)
Visit a Giant Gingerbread Display
Decorating Gingerbread houses was always a fun tradition in our house. So getting to see these creative masterpieces is always a delight. Built from spiced gingerbread and decorated with icing and candy, they turn simple ingredients into creative masterpieces.
Each December, the Wentworth-by-the-Sea resort unveils a massive gingerbread house which becomes part of their holiday decor. Beginning in early December, the display is open to the public for viewing.
The scale of the Gingerbread house is quite impressive with some that have measured 7 feet wide and 5½ feet tall. The massive cookie creation is built with real gingerbread, butter, sugar, molasses and flour and decorated with candy, icing, and thousands of candies.
If you love gingerbread houses (or just want to see something totally cool), you need to check this out!
Wentworth-by-the-Sea (588 Wentworth Rd, New Castle, NH)
Enjoy a Festive Drink
Warm up with a holiday cocktail in a beautifully decorated setting.
In recent years, pop‑up holiday bars have become the rage, with restaurants across New England transforming into immersive, Instagram‑worthy winter wonderlands.
Among the standouts is the Miracle at The Goat. Their Portsmouth and Newburyport locations get decked out in twinkling lights and quirky holiday touches. Stop in and have a holiday‑themed cocktail with fun names like the Christmapolitan and Rum Run Reindeer.
Miracle at The Goat is only at their Portsmouth (142 Congress St.) and Newburyport (54 Merrimac Street) locations. Seating is on a first‑come, first‑served basis, so you may need to wait. The Miracle season typically runs from mid‑November through early January.
Other Miracle locations can be found around New England and all over the US.
Have a Little Wine with Your Winter Lights
Want to experience the magic of twinkling holiday lights? Stop in at LaBelle Winery, where you can sip award‑winning wine while strolling along paths illuminated by millions of sparkling lights.
LaBelle Lights transforms its winery into a dazzling winter wonderland that’s perfect for families, friends, and lots of fun.
Grab a festive drink and stroll through the illuminated installations and tunnels, including the “Snowflake Forest, the whimsical “Bubble Bridge” and a festive “Candy Cane Lane.
Beyond the lights, you can visit the on‑site market where they have all sorts of goodies, gifts and a wall full of wine. You can also grab food at the “Snowflake Snack Shack,” or make a reservation for indoor dining at the winery’s restaurant.
This holiday display is open from mid-November through mid‑January each season. General admission is $20 and discounted for seniors and children. Be sure to check their schedule for discount days, Santa visits and special events.
Labelle Lights (14 NH-111, Derry, NH)
Explore the SoWa Winter Market
While Boston’s Snowport Winter Market brings the holidays outdoors to Boston’s Seaport, the SoWa Winter Festival offers an equally festive experience indoors.
As New England’s largest indoor holiday marketplace, it’s become a favorite spot for those who want the magic of a holiday market without braving the cold. And to be honest, I’m one of those people!
The SoWa Winter Festival takes place at the SoWa Power Station, located in Boston’s South End. During the holiday season, this space becomes a bustling winter marketplace with more than 120 artisans, makers, and specialty food vendors.
Inside, you’ll discover unique handcrafted gifts, gourmet treats, and home decor. Upstairs you can stop by the bar to enjoy festive cocktails while listening to live music in a fun and festive atmosphere.
The SoWa Winter Market is a great outing with friends and family to get some holiday shopping done while supporting local artisans.
The SoWa Winter Market (SoWa Power Station, 550 Harrison Ave, Boston, MA) opens Black Friday and runs through the end of December. Closed Mondays. Admission is $10 and parking is available for $10 Cash only.
Celebrate Vintage Christmas in Portsmouth, NH
Portsmouth, NH is one of the most festive towns with its Vintage Christmas celebration which began in 2005. In fact, in 2023, House Beautiful named this seaside NH town the 4th Most Festive Christmas town in the US.
During Christmastime, this charming coastal city transforms into a festive wonderland complete with a glowing parade, tree lighting ceremony and beautifully decorated historic homes.
A highlight of the event is a visit to Strawbery Banke, where you can take a cozy Candlelight Stroll through centuries-old buildings illuminated by hundreds of lanterns. Experience what the holidays were like in earlier times watching hearth cooking demonstrations and enjoying live period music and caroling.
The downtown is also bursting with holiday cheer with horse‑drawn carriage rides, a free vintage trolley shuttle and festive window displays. Other seasonal highlights include holiday concerts and shows at The Music Hall theater, gingerbread-house contests, and outdoor ice skating at the pond rink.
Where to Stay:
- Hotel Thaxter – A beautifully restored 1860s boutique hotel in downtown Portsmouth with a cozy restaurant just steps away from the the city’s downtown.
- Homewood Suites by Hilton – This modern, suite-style hotel in located in the heart of the city with easy walking access to Portsmouth’s shops, restaurants, and waterfront.
Vintage Christmas (Portsmouth, NH)
Visit a Festival of Trees
Across New England, Festival of Trees events light up the season, showcasing beautifully decorated Christmas trees, festive displays, and fun holiday experiences for visitors of all ages.
These celebrations help support local charities and community causes, giving visitors a chance to celebrate the season while giving back.
The Sea Festival of Trees in Salisbury, MA brings holiday magic to the Blue Ocean Event Center. This community fundraiser has more than 150 decorated and glowing Christmas trees on display. Each tree is donated by local residents and businesses and raffled off at the end of the event.
Stroll through each room to find your favorite designs and take a chance at winning one to take home. These themed creations are the perfect inspiration for decorating your own tree while supporting the local community.
Be sure to grab a sweet treat or cocktail while you wander about or take a twirl on the indoor “Seaside Ice” rink.
Make it a fun filled holiday outing and check out the special events like Sippin’ Santa Girls Night Out, Ugly Sweater night or Brunch with Santa and The Grinch.
Admission is $10 at the door. Once inside, raffle tickets, skates and other gifts are available for purchase.
Sea Festival of Trees (Blue Ocean Event Center – 4 Ocean Front N, Salisbury, MA)
Experience Kennebunkport’s Christmas Prelude
Kennebunkport’s Christmas Prelude is one of New England’s most beloved holiday traditions. Since 1982, this coastal Maine town has welcomed visitors from near and far to celebrate the season in true New England style. The town has even been recognized as a top Christmas town by HGTV and Country Living.
For two weeks each December, the town transforms into what feels like a Hallmark Christmas movie come to life, with twinkling lights, decorated trees, and dazzling holiday storefronts. Some highlights of the event include the Dock Square tree lighting, visits with Santa, a Pooch Parade and candlelit caroling at the Franciscan Monastery.
Set along a picturesque harbor, Christmas Prelude offers a magical experience that captures the nostalgic spirit of the season. With so much going on, you may want to stay a while.
Where to stay:
- Kennebunkport Inn – If you’re looking to stay where the action is, this is the perfect place. Located right in the center of town, this beautiful Inn is walking distance to shops and restaurants.
- The Boathouse is a boutique hotel and restaurant overlooking the Kennebunk River and it’s walking distance to Dock Square.
Christmas Prelude (Kennebunkport, ME)
See a Lighthouse All Dressed Up
Experience New England’s coastal charm with a lighthouse decked out for the season.
During the holiday season, many New England lighthouses get decorated with lights, wreaths, and decorations.
The iconic Nubble Lighthouse in York, Maine is one of those lighthouses that becomes a festive beacon along the rugged New England coast. Nestled on its rocky island, the lighthouse is illuminated with twinkling lights that reflect off the Atlantic waters, creating a magical winter scene.
For more holiday festivities, stop by the towering Lobster Trap Christmas Tree, located at Fox’s Lobster House across from the lighthouse. Together, the Nubble Lighthouse and lobster trap tree make a great spot to snap a photo to capture the spirit of the season and the charm of Maine’s seaside towns.
Nubble Light (Sohier Park, Sohier Park Rd, York, ME)
Attend a Classic Holiday Show
If you’re looking for a fun outing, seeing Charles Dickens’ “A Christmas Carol” brought to life on stage is a perfect way to celebrate the season.
Since 1966, the North Shore Music Theater (NSMT) has played a vital role in New England’s performing arts scene. A highlight of its holiday season is its original adaptation of Charles Dickens’ classic story of Ebenezer Scrooge that has been a tradition since 1989.
The production is full of dazzling special effects, dramatic lighting and offers a festive, immersive experience that captures the spirit of the season. Experiencing this production at least once is a must and making it a tradition is even better.
North Shore Music Theater (54 Dunham Road, Beverly, MA)
Get Creative with DIY Gifts
Handmade gifts are always special, and tapping into your creative side makes the process even more fun. Attend a workshop where you can craft something beautiful to decorate your home or give as a heartfelt gift.
Studios like Hammer & Stain offer guided DIY sessions to make holiday signs, ornaments, seaglass trees, and more.
I love Hammer & Stain North Shore (211 Rantoul St, Beverly MA) but there are other locations in New England and in other parts of the US.
Volunteer or Donate Locally
The holiday season is also a time to pause and think about those who may be less fortunate. While many families enjoy festive traditions and activities, many others are facing challenges.
Supporting local toy drives, coat drives, or community nonprofits is a simple way to spread the warmth this season.
Consider taking a moment to donate to local organizations like Toys for Tots, Cradles to Crayons, regional food pantries or other local charitable organizations.
Even a small gesture, a new toy, a warm winter coat, a bag of groceries, or a couple of hours volunteering, can brighten the season for someone who needs it most.
Wishing you all a joyful, peaceful, and meaningful holiday season.
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