Holiday Strolls 2024
Boston and Beyond
These events blend shopping, entertainment, and holiday charm, making them must-see experiences:
Boston's Beacon Hill Holiday Stroll (Highly Anticipated)
Date: December 5, 2025
Time: Evening (typically begins around 6 PM)
Highlights: Live holiday music, festive shopping, and the lighting of the Christmas tree on Charles Street. Explore the charming historic streets of Beacon Hill adorned with lights. The shops along Charles Street (some of Dev’s favorites) stand out. The bookstore is the only one of its kind (so warm inviting and quite beautiful), Upstairs Downstairs (where Dev gets much of her home furnishings) is sophisticated and fun...great art too! And, Charles Street even has a cat bar (yes, a kitty cat café called Sanctuary. You can enjoy your lavish pastries in the company of some purring paws. Yes, real live cats live here and are happy to have your company. There’s no place like Charles Street. And since its one of Devon’s favorites, you know its GREAT!
Christmas by Candlelight at Old Sturbridge Village
Dates: Weekends throughout December
Highlights: Step back in time to experience 19th-century holiday traditions with live music, tree lighting ceremonies, and festive demonstrations.
Christmas in Newport (Newport, RI)
Dates: Entire month of December (kickoff on December 1)
Highlights: Tree lighting, mansion tours, ice skating, and performances, including "The Nutcracker" at Rosecliff Mansion.
Discover Newport
Christmas Prelude in Kennebunkport 2024
Dates: December 5–15, 2024
Kennebunkport's Christmas Prelude is a two-week celebration filled with traditional holiday cheer and creative local events. Highlights include the Dock Square Tree Lighting Ceremony (December 6), where caroling and community joy mark the season's official start, and the Lobster Trap Tree Lighting in Cape Porpoise. Families can enjoy unique activities like the Hat Parade, Pooch Parade, and Storybook Christmas at the Kennebunkport Conservation Trust. Adults can indulge in the Fire & Ice Festival at the Nonantum Resort, featuring ice sculptures, bonfires, and elegant holiday treats. Explore charming shops, bonfires, and festive trolleys during this enchanting event. House Tours, and Wine Tasting, Hot Cocoa served, Carolers in the streets, and Candlelight singing are just a small part of what is offered in this fantastical annual event. FYI, going during the week might be best. We went last year and arrived smack dab in the middle of a Saturday afternoon, and it felt more like NYC!
Visit Maine Net
Nantucket Christmas Stroll 2024
Dates: December 6–8, 2024
The Nantucket Christmas Stroll offers a cozy, festive atmosphere with Santa arriving via a Coast Guard cutter, carolers in Victorian attire, and beautifully decorated streets. We find it like going back in time with the cobblestone streets and old fashion street lights. Nantucket is truly like no other place and the Nantucket Stroll (and we’ve been to them all), is our most beloved.
The holiday market features local crafts, while restaurants and inns provide warm, seasonal delights, some of the decorating going all out and hard to beat! This event is part of Nantucket Noel and draws visitors with its small-town charm and traditional spirit. This is not to be missed. Accommodations may be limited so start planning for 2025!
Grey Lady GirlSomeone recently asked us how did the Nantucket Stroll begin. We did some researching and this is the story...
More than 50 years ago, the originators of the first Nantucket Christmas Stroll were trying to discourage islanders from traveling to Cape Cod, 30 miles across Nantucket Sound, to do all their holiday shopping. They were hoping island residents would do their shopping locally.
Rewind to 1973, a year when local merchants kept shops open late that first Friday in December, inviting locals to do all their holiday shopping on-island. That evening, christened as a “Christmas Shoppers Stroll,” was a mere three hours in duration and was a huge success. Shopkeepers entertained shoppers with wine, hot chocolate, tea, mulled cider, fruitcake, and holiday cookies while they perused crafts, books, clothes and wares, and other holiday gift items. In subsequent years, the event grew exponentially, drawing larger crowds until it became a nationally- and, ultimately, internationally-renowned holiday event. Now organized by the Nantucket Island Chamber of Commerce, this popular and festive event is typically held during the first full weekend of December.
This year’s Nantucket Christmas Stroll is being celebrated as the 50th because Stroll was canceled one year during the pandemic. The event will feature more than 100 decorated holiday trees throughout the downtown area, along with a 20-foot tree at the top of Main Street. All these trees will be lit up at dusk the day after Thanksgiving with a special Illumination Ceremony led by Nantucket’s Town Crier: a fun family gathering with caroling.
The A-LystOnce again this year, the Nantucket Historical Association is transforming their Whaling Museum into a glittering winter wonderland. Starting on December 6 and continuing through the month of December, more than 50 uniquely decorated and crafted trees designed by local businesses, artists, individuals, and non-profit organizations make up the Festival of Trees showcase. The NHA often hosts additional holiday events: visit their website at nha.org for details.
The Fun Never Ends
In addition to its longstanding traditional events, the Nantucket Island Chamber of Commerce has announced weekend highlights and activities on Stroll Saturday that include: the sale of Annual Stroll pins and merchandise; Storefront and Tree Decorating Contests; a downtown marketplace from 10 am to 3 pm featuring food, crafts, beverages; live entertainment on a stage set up on Main Street; and the arrival by boat of Santa Claus announced by Nantucket’s Town Crier. Island business people are walking tours, book signings, hikes, special sales, holiday theatre performances, concerts, and stroll receptions. For exact details, dates, times, and locations of this year’s events, visit the Insider’s Guide to Nantucket: Nantucket.net.
Over the decades, the Nantucket Chamber of Commerce has enlarged and improved Christmas Stroll weekend, but it is the island’s warm welcome and hospitality that add to the holiday spirit and feeling of fellowship on Nantucket Island.
Invitation Night - Newburyport, MA
If you love the idea of the Nantucket Stroll but don’t want to get on a boat or a plane and sail thirty miles out to sea, there is always invitation night in Newburyport. This historic town comes to life at the holidays and merchants go all out to lure the customers into their shops. They serve champagne, fabulous appetizers, homemade cookies and punch, and so much more. There is a tree lighting ceremony and carolers, and even decorated Pedi cabs to take your around town.
Having attended this fantastic holiday event December for the last two decades, we think their website says it best: Mark your calendars, book a babysitter, and call your friends to make plans for three great nights in Newburyport! Enjoy merchant hospitality, live entertainment, shopping, and dining in beautiful and festive downtown Newburyport, The Tannery, Merrimac Place, and Horton's Yard. Spend your evening strolling from shop to shop as you stock up on holiday gifts while enjoying munchies and beverages offered by local merchants. These Newburyport Invitation Nights will get you in the holiday spirit and will turn any Scrooge into Kris Kringle.
Please join us on the first 3 Fridays in December from 6:00PM - 9:00PM... like we said, they mean it! Mark your calendars and get to Newburyport. Ho Ho hope to see you there
Only In Your StateAnd, if you go, our favorite shop is Partridge in a Bear Tree....Stop there first for some amazing holiday punch (a secret recipe) the late owner, Kevin took it to heaven with him!
Wellesley Holiday Stroll
Date: December 8th, 2024
Not to be outdone, we’re excited to tell you about the one and only Wellesley Stroll!
We’ve had the pleasure of attending this charming event (yes, you might call us professional strollers), and it’s always a delightful experience. One of the highlights is the fantastic scavenger hunt, which not only offers some terrific prizes but also adds an interactive element to the festive fun. You’ll find yourself exploring the town in search of holiday surprises, and it’s an activity that’s perfect for families and groups of friends alike.
Adding to the seasonal magic, there are talented carolers serenading visitors with classic holiday tunes, creating a cozy, nostalgic atmosphere. And this year, rumor has it that Barbie herself will be making a special appearance, bringing a touch of glamour and whimsy to the event. Whether you’re a Wellesley local or visiting from out of town, the Wellesley Stroll is the perfect way to soak up the holiday spirit, discover unique local shops, and enjoy festive cheer with the community.
The Swellesley ReportDozens of carolers will be strolling throughout Wellesley Square.
12:00-5:30: Meet Frosty and Rudolph as they stroll throughout the Square.
1:00-5:00: Pictures with Santa on Central Street.
5:00-5:30: Town Tree Lighting Ceremony at the Wellesley Square Fire Station.
And be sure not to miss the scavenger hunt with terrific prizes!
These events capture the essence of New England holiday traditions, offering memorable experiences all! WE can never have enough holiday strolling! It’s in our DNA!