Great Holiday and Christmas Season Day Trips Near Long Island

Delight in the holiday magic at Hersherypark. Photo courtesy of the park
Delight in the holiday magic at Hersherypark. Photo courtesy of the park

While we all have plenty to do this time of year, it's important we remember to schedule some family time to celebrate the joy of the Christmas season.

Luckily for us, there's no shortage of holiday happenings on Long Island. But there's also a lot going on not far from here, making for a fantastic day trip or quick weekend getaway. From Manhattan to Mystic; from Westchester to Pennsylvania; and plenty of stops in between, we've rounded up some perfect holiday trips for your family to consider this year.

For more suggestions for seasonal entertainment, check out our guide to holiday fun on Long Island, our roundup of great December things to do, and our events calendar.

Christmas and Holiday Day Trips from Long Island, 2021 

Experience a fantastic show in NYC such as 'Twas the Night Before... Photo by Errisson Lawrence

New York City

Is there any place more magical than New York City during the holidays? We don't think so. Leave the car at home, hop on the Long Island Rail Road and head straight to Penn Station. From there, walk down 34th Street to Macy's Herald Square. Marvel at Macy's windows and stop in and say hi to Santa in Santaland. Make your way down Fifth Avenue, where you'll see more store windows decked out for the holidays, and then head to Rockefeller Plaza to see the city's iconic tree. While you're there, do some ice skating or watch other skaters as you sip hot cocoa. Also, be sure to visit Manhattan's famous toy store, FAO Schwarz, in its 20,000-square-foot location. There are plenty of shows to take in as well, including the famous Rockettes at the Radio City Christmas Spectacular; 'Twas The Night Before...By Cirque du Soleil at the Hulu Theater at Madison Square Garden; or one of the many performances of the Nutcracker around the city. One of our seasonal favorites, the Holiday Train Show, delights at the New York Botanical Garden until January 23, 2022. Access the botanical garden via the Bronx River Parkway, Metro-North Railroad, the B or D subway lines to Fordham Road, or the 2 or 5 subway lines to Bronx Park East.

RELATED: Polar Express Trains in the NYC and LI Area This Holiday Season

The Brooklyn neighborhood of Dyker Heights lights up for the holiday season. Photo by Alex Fitzpatrick

Dyker Heights, Brooklyn

If you're feeling adventurous, rather than return to Long Island after your NYC excursion take the R or D subway lines to the Dyker Heights neighborhood of Brooklyn. There, you'll find block after block of houses extravagantly lit up for the holidays. The destination is super popular, attracting visitors from all over the country, even the world. You can drive there, but parking is difficult, so mass transportation is your best bet. There are several tours you can take through A Slice of Brooklyn Bus Tours. The neighborhood's Facebook page has more information and updates; and for more fun things to do in the area, check out our guide to Brooklyn neighborhoods. If coming directly from Long Island, take the LIRR to Atlantic Terminal in Brooklyn, then take the D subway to 71st Street. 

Valhalla, New York

Take a ride up to Westchester County, about an hour north of Long Island, for a ton of holiday fun. Visitors can fuel up for the day at one of the many Breakfast with Santa events in the area. Then after a visit with St. Nick, watch a performance of A Christmas Carol - The Musical at the White Plains Performing Arts Center, one of the many kid-friendly holiday shows in the area. End the trip with a drive through Westchester's Winter Wonderland at Kensico Dam Plaza Park. Sponsored by the Westchester Parks Foundation, kids and grown-ups will thrill at the numerous illuminated exhibits and holiday animations, including several 30-foot tall snowflakes and an elf disco, both of which are new this year.

RELATED: Great Holiday Light Shows on Long Island for 2021

Make sweet memories at Hersheypark this holiday season. Photo courtesy of the park

Langhorne, Pennsylvania

Hersheypark Christmas Candyland in central Pennsylvania (about a three- or four-hour drive from Long Island) is a sweet day or weekend destination for the whole family. It truly is a winter wonderland, with rides for every age group and the entire park decorated with more than 4 million twinkling lights. There's live entertainment, a choreographed light show, animated displays, and of course, the big guy himself and his reindeer. You can also check out the park's zoo and tour Chocolate World. If you choose to stay overnight, there are special holiday packages for the Hershey Lodge and The Hotel Hershey. Other theme parks hosting holiday events include nearby Sesame Place and Six Flags in Jackson, New Jersey.

RELATED: Holiday Train Shows for Long Island Kids in 2021 

Enjoy the sounds of the holidays at Mystic Seaport Museum's annual Community Carol Sing. Photo courtesy of the Mystic Seaport Museum

Mystic, Connecticut

Take the ferry from Orient Point to New London, Connecticut (about a 90-minute trip) and then drive east 10 miles to Mystic, where there are plenty of holiday sites to see. The main attraction is Mystic Seaport Museum. Don't miss the museum's Lantern Light Tours, a re-creation of Christmas Eve, 1876, where visitors walk through the town and get a ride on a horse-drawn carriage. On Sunday, December 19, attend the festive Community Carol Sing. During the week between Christmas and New Year's, special holiday events take place during Holiday Magic!. During this time, visitors can explore the museum's 19th-century seafaring village, historic ships, and maritime exhibits. Be sure to visit Olde Mistick Village, where you can stroll through the 18th century-themed village and see the many shops and restaurants. 

Hartford, Connecticut

To visit this New England capital city, take the roughly 75-minute ferry from Port Jefferson to Bridgeport. From there, head north on Interstate 95 to I-91 and Hartford, where you'll find the majestic family home of one of America's most beloved authors, Mark Twain, which is decorated for a late 19-century Christmas. Hartford is also home to the Connecticut Science Center. While there, be sure to check out the museum's Butterfly Winter Wonderland. Don't leave Hartford without a visit to Bushnell Park, where Winterfest is in full swing with free skating, rentals, lessons, and more. Before you head home, enjoy dinner or lunch in one of many family-friendly restaurants in and around Hartford.

RELATED: Where Long Island Kids Can Dine with Santa This Holiday Season

Historic Philadelphia offers lights, ice skating, Santa sightings, and an authentic Christmas market. Photo courtesy of Visit Philly


There is so much to do and see in Philadelphia this time of year that it should be a must-visit destination for every Long Island family. From the season-long Electrical Spectacle Holiday Light Show to an outdoor holiday market that's reminiscent of a traditional German Christmas market and holiday light shows, a visit to Philly will get the whole family feeling over-the-top festive. If you have the time, be sure to take in a Disney on Ice performance. Then practice your moves as you go ice skating and more at the Blue Cross RiverRink Winterfest. Finish the day with a visit to the Morris Arboretum Holiday Garden Railway.

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