The holidays are a magical time of year on Long Island. From various light displays and holiday festivals, to Gatsby-era mansions decked for the season in stunning décor, to snow covered beaches, cozy cafes welcoming visitors in to defrost amid holiday shopping, and more – the enchantment of the region during the winter season unfolds like scenes from a Hallmark Christmas movie.
Small towns and villages throughout the island come alive with festive charm as their holiday lights twinkle throughout the streets, and their local shops and restaurants fill with cheer of those looking to soak up the delights of the season.
Instead of staying in to watch this year’s latest holiday flick (we all know how they end!) why not get out and experience that small town holiday charm for yourself?
Read on for the perfect list of places to visit this season, ideal for surrounding yourself in the magic of the holiday season with friends and family, all while living out your main character Hallmark Christmas movie dreams.
Port Washington is a lovely waterfront hamlet located in Nassau County on the North Shore. Only 17 miles from New York City, Port Washington is the perfect choice to escape the everyday, busy city routine and indulge in some holiday spirit – that definitely sounds similar to the plot of a Hallmark Christmas movie! Quaint streets adorned with sparkling lights lead to charming shops, offering unique holiday treasures. The waterfront glistens with seasonal decorations, providing a picturesque backdrop for festive strolls. From community celebrations to waterfront festivities, Port Washington invites you to experience the holidays in a setting that blends coastal charm with yuletide magic.
Searching for that quintessential holiday charm? Milleridge Village at the historic Milleridge Inn is your answer. Located in Jericho, every day is Christmas at this collection of specialty shops. Enjoy the spirit of the season in the year-round Christmas Shoppe, the General Store, the Café, Candy Shoppe, bakery, and restaurant. Whether looking for the perfect holiday gift, a delicious meal, a sweet treat, or just wanting to take a Christmas-themed stroll with a loved one, this hidden treasure on Long Island is perfect for any occasion!
Oyster Bay invites you to savor the magic of Christmas in a setting that combines historic allure with North Shore coastal grace. The town's maritime heritage is illuminated by the glow of seasonal decorations, casting a warm glow over its natural beauty. Visit for a meal and some holiday shopping amid the booming dining scene and unique shops or embrace the history of the small town this holiday season with a trip to Planting Fields (pictured above), decked out in beautiful holiday décor, or Sagamore Hill, the former home to 26th U.S. President, Theodore Roosevelt.
Babylon Village transforms during the holiday season to radiate a cozy and welcoming vibe to all who visit, capturing the essence of a classic Christmas. The charming streets, adorned with greenery and holiday lights, lead to boutique shops offering the best holiday finds. Restaurants and bars such as Mary Carroll’s, The Villager, The Local, and Lily Flanagan’s, as well as the decadent Torta Fina Bakery, invite you to savor good food and even better drinks in a warm and cheerful atmosphere.
Cold Spring Harbor
Discover the magic of the season in Cold Spring Harbor, a delightful small town offering festive joy for every holiday enthusiast. Explore the charming shops like My Favorite Place and Say La Vie, where you can find treasures to wrap in holiday cheer. Then, satisfy your hunger at local eateries, bakeries, and cozy coffee shops such as Sweetie Pies on Main. Dive into the Christmas spirit with a visit to this North Shore gem, sure to make your holidays memorable.
Dressed in holiday charm, Huntington's chic downtown becomes a festive retreat this time of year, offering both upscale dining options as well as more casual choices, perfect for any holiday celebration or night out. Indulge in the warmth of the season at the harbor front steakhouse Prime or the brunch hot-spot Toast & Co. Immerse yourself in the arts and culture hub, where The Paramount hosts seasonal concerts, comedy shows, and special holiday events. To complete the Christmas magic, venture to Oheka Castle to experience the enchanting estate in all of its glory decorated for the holiday season.
Step into a Christmas postcard in the charming Northport Village, a historic waterfront gem on the Gold Coast, settled in the 1600s. Wander through the village, where the nostalgia of the early 1900s lingers through various shops, ice cream parlors, and old, winding trolley tracks that run through town. Immerse yourself in the holiday spirit with dinner and a show at the historic John W. Engeman Theater, a treasure since 1912. For a merry finale, visit Del Vino Vineyards for a festive winery experience.
Stony Brook Village
In the heart of the holiday season, the picturesque village of Stony Brook transforms into a Christmas haven steeped in historic tales. Dive into the festive spirit by exploring the town's rich history. Unwind in the charming downtown adorned with seasonal decorations, offering quaint eateries and premier shops. Fan of Billy Joel? Be sure to stop by the Long Island Music & Entertainment Hall of Fame in the heart of the village to explore the brand new, first of its kind Billy Joel dedicated exhibit, showcasing several years of rare memorabilia!
During the holidays, Port Jefferson transforms into a charming, seaside winter wonderland, especially during its annual Dickens Festival (pictured above). Its walkable downtown through popular shops and restaurants dressed in holiday décor invite everyone to experience a joyful and memorable holiday season visit. Grab a meal at one of the many establishments, such as Ferryman’s Grille or Local’s Café. Looking to stay overnight? Danfords Hotel & Marina has you covered with beautiful harborside lodging.
Photo Credit: Jeremy Garretson
Celebrate the holiday season in the picturesque waterfront village of Greenport, where the air is infused with festive cheer. From local families, to visitors, historians, and boat lovers, all alike find themselves living their best Hallmark Christmas movie-type lives while visiting this nautical escape in the festive off-season. The waterfront community comes alive with twinkling lights and décor dressing its vibrant downtown as activities and entertainment spill from the doors of local restaurants, bars, hotels, shops, and more. While in town, check out places like Claudio’s Restaurants, American Beech hotel and restaurant, and Greenport Harbor Brewing Co.
Hamptons & Montauk
Escape to the famed Hamptons on Long Island’s South Fork for a Christmas like no other, treating yourself to a setting of unparalleled coastal elegance. Amid the upscale retreats, discover a winter wonderland that marries sophistication with festive cheer. Whether stopping by Sag Harbor, Bridgehampton, Southampton, Easthampton, or venturing to the end of the island for Montauk, find sprawling estates and downtowns along the way, adorned with elegant decorations lining the streets, exuding luxury and holiday spirit. Upscale boutiques in each downtown offer curated gifts, and gourmet restaurants serve delectable seasonal fare. Bundle up and enjoy serene walks on pristine beaches then cozy up and relax at a spa or settle into a charming overnight stay at places like Topping Rose House in Bridgehampton or Gurney’s Resort in Montauk.