The holidays are a magical time of year on Long Island. Revel in the season by ice skating at one of Long Island’s many outdoor ice rinks or head to a local historic theater to see a Broadway-caliber performance of a favorite Christmas play in an intimate setting. See extravagant, larger-than-life glowing art installations or tour a Gatsby-era mansion decked for the season.
You can savor the small-town charm of Long Island’s many downtown villages as they come to life with festive concerts and events like the Dickens Festival in Port Jefferson, Flying Santa at Fire Island Lighthouse, Winterfest, and dozens of tree-lighting celebrations. While you’re there, explore the mom-and-pop Main Street shops for unique gifts for loved ones. Or head to the East End where you can drive a tractor through rows of firs, spruces and pines at more than a dozen Christmas Tree Farms where you can cut your own!
With so much to do, we rounded up the most enchanting holiday spectacles happening across Long Island this year that are worth the Long Island Rail Road trip.
Mr. Grinch Christmas Pop-Up (Farmingdale)
Now – January 8, 2023
It's The Most Wonderful Time of the Year! Yuck! Who is the mean fellow, with his skin all green and his teeth all yellow? Mr. Grinch! Visit the Christmas pop-up cocktail experience inspired by the movie: The Grinch! Join us for a stink, stank, stunk time and Christmas cheer. Indulge in Christmas themed cocktails and a small plate food menu PLUS a visit from Mr. Mean Green himself with table side interactions and photo opportunities! (Adults 21+ only).
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the Homewood Suites by Hilton Long Island - Melville, the Hilton Garden Inn Melville, or the Courtyard by Marriott Republic Airport Long Island / Farmingdale.
HOW TO GET HERE: Take the Ronkonkoma Branch from Penn Station to Farmingdale. Located at 300 Main Street, The Christmas Club is an 8-minute walk from the station.
LIRRHuntington Holiday Spectacular (Huntington)
Now – January 10, 2023
The Holiday Spectacular is back this year on Wall Street in Huntington with nightly festivities including lights, music, holiday surprises, and a tree and menorah lighting. Over five weeks, culminating on January 10, 2023, guests can visit Wall Street daily, to view this newly created Winter Wonderland. Local businesses will participate with special deals to promote the holiday season in this picturesque downtown.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the Hampton Inn & Suites Huntington Downtown, the East Norwich Inn, or Oheka Castle.
HOW TO GET THERE: Take the Port Jefferson branch from Penn Station to Huntington. Wall Street is a 6 minute rideshare from the station.
26th Annual Dickens Festival (Port Jefferson)
December 2- 4, 2022
The Village of Port Jefferson will magically transform into the Dickensian era with streets filled with roaming characters such as Father Christmas, Dickens Mayor, Scrooge, the Town Crier and the beloved chimney sweeps. The events are open to the public and most attractions are free of charge, so everyone – from the very young to the young at heart can join in the fun.
The festivities will feature many returning favorites: ice skating at the Village Center, a cappella performance by choirs and harmony groups, Nutcracker performances, magic shows by The Great Wizard of the North, and fine musical performances by area musicians. In addition, this year’s festival will feature Theater Three’s Annual production of A Christmas Carol.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Danford’s Hotel & Marina in Port Jefferson or Three Village Inn in Stony Brook.
HOW TO GET HERE: Take the Port Jefferson branch from Penn Station to Port Jefferson. Downtown Port Jeff is a 5-minute rideshare trip.
Freeport’s Nautical Mile of Lights Annual Boat Parade (Freeport)
December 3, 2022
Sponsored by the Freeport Chamber of Commerce, this unique event showcases festively decorated boats along Freeport’s Nautical Mile. Boat owners go all out decorating their vessels, and homeowners along the route adorn their yards with lights.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at The Freeport Inn & Marina or Best Western Mill River Manor in Rockville Centre.
HOW TO GET HERE: Take the Babylon branch from Penn Station to Freeport. The marina is a 6-minute rideshare from the station.
Chabad Center for Jewish Life Menorah Lighting (Merrick)
December 18, 2022
The Chabad Center for Jewish Life of Merrick-Bellmore-Wantagh presents their grand menorah lighting and parade with a fire truck and vintage car with rooftop menorahs! Come for the grand 12-foot menorah lighting, hot latkes, delicious donuts, music, dancing, and more!
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at The Freeport Inn & Marina, Long Island Marriott, or The Allegria Hotel in Long Beach.
HOW TO GET HERE: Take the Babylon branch from Penn Station to Merrick. The outdoor festivities take place at the LIRR parking lot, starting at 3:30 PM.
Waterdrinker Family Farm Winter Wonderland (Manorville)
Now – December 2022
Waterdrinker Family Farm’s Winter Wonderland is now open! Come and enjoy hot cocoa by the Airstream Christmas Village. With activities such as ice skating, mini golf, an obstacle course, gingerbread village, fire pits and s’mores, ice skating, and so much more, there’s something for everyone! And their Christmas Tree Lot is open so you can pick out the perfect tree for the season. The Winter Wonderland is open Wednesday-Sunday throughout the month of December.
OVERNIGHT STAY OPTION: Make it a weekend getaway by taking advantage of the MTA Away Deal to Hotel Indigo Long Island - East End or stay at The Preston House.
HOW TO GET HERE: Take the Ronkonkoma branch from Penn Station to Riverhead. The farm is a 13 minute rideshare, or buy the MTA Away Deal, which includes round-trip transfers to Hotel Indigo.
Christmas Land (Tanger Outlets Deer Park)
Now – January 8, 2023
Get your shopping done while experiencing all things Christmas! Explore the world of Christmas cheer and be transported to an imaginative land with a one-of-a-kind experience. Christmas Land is an interactive installation that celebrates the vibrant colors and traditions of your favorite holiday with over a dozen environments across 20,000 square feet of space.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at Jake’s 58 Casino Hotel or the Hilton Garden Inn Islip/MacArthur Airport.
HOW TO GET HERE: Take the Ronkonkoma branch from Penn Station to Deer Park. Tanger Outlets provides a free shuttle from the station to the festivities.
A Christmas Story at the John W. Engeman Theater (Northport)
Now – December 31, 2022
In the heart of quaint Northport village that still bares the trolley tracks last used in the 1980s, the John W. Engeman Theater at Northport is a premier year-round professional theater that casts its actors directly from the Broadway talent pool. This holiday season, their main stage show is the beloved tale, A Christmas Story, with performances featuring Broadway talent Lanene Charters as Miss Shields and Jennifer Evans as the mother. Their winter children’s shows include Frosty, running from November 26 to December 31, and Frozen Jr., running from February 4 to March 5.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the Chalet Inn & Suites or Hampton Inn & Suites Huntington Downtown.
HOW TO GET HERE: Take the Port Jefferson branch from Penn Station to Northport. The theater is a 6 minute rideshare from the train station.
Winter Lantern Festival (Smithtown)
Now – January 8, 2023
Immerse yourself in an awe-inspiring whimsical world of light that celebrates Chinese culture. The NYC Winter Lantern Festival, a vibrant Chinese-inspired holiday light show, will dazzle families on Long Island this winter. The artistic event made its debut this year at Smithtown Historical Society as the Suffolk Winter Lantern Festival. Over 150,000 handmade lanterns are illuminated in the shapes of animals, flowers, dinosaurs and more.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at the Smithtown Inn Town House Motel or Three Village Inn in Stony Brook.
HOW TO GET HERE: Take the Port Jefferson branch from Penn Station to Smithtown. The festival is a 5 minute rideshare from the station.
LuminoCity Festival, “Pure Magic” (East Meadow)
Now - January 8, 2023
Follow Lumi, the magical lightbulb who hails from Unicorn Kingdom, through a wondrous world of ancient civilizations, illuminated jungles, and glowing art installations. LuminoCity is partnering with Nassau County this holiday season to bring you a world of magical light installations that come to life at Eisenhower Park in East Meadow. Check out the MTAaway Deal to save 10% off tickets to this family favorite!
This year’s theme, “Pure Magic” will deliver a state-of-the-art production that brings art, light, and color to life through remarkable displays. Children will be in awe of the mystical, fantastical displays illuminating 17 acres of grounds.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at La Quinta Inn & Suites by Wyndham Garden City, The Garden City Hotel, or Coliseum Inn & Suites – Garden City.
HOW TO GET HERE: Take the Ronkonkoma or Port Jefferson branch from Penn Station to Westbury, then catch an 8 minute rideshare to the event.
Shimmering Solstice at Old Westbury Gardens (Old Westbury)
Now - January 1, 2023
Shimmering Solstice at Old Westbury Gardens is an unforgettable walkthrough experience of holiday lights, sights, and sounds! Be prepared to be enchanted by magical light displays and seasonal soundtracks that are set along Old Westbury Gardens’ beautiful paths that will lead you through the world-famous Walled Garden, Rose Garden, South Lawn and Allée, just to name a few.
Designed for Old Westbury Gardens by Lightswitch (a collective of internationally recognized lighting, media, and visual designers), Shimmering Solstice allows guests to experience what is familiar every day in a whole new shimmering light. For this year’s dramatic finale, an even more astonishing finale show will be displayed on the south face of Westbury House.
OVERNIGHT STAY OPTION: Make it a weekend getaway by staying at The Garden City Hotel or SpringHill Suites Carle Place Garden City.
HOW TO GET HERE: Take the Ronkonkoma or Port Jefferson branch from Penn Station to Westbury, then catch an 8 minute rideshare to Old Westbury Gardens.
