Discover the magic of maritime adventures at South Street Seaport Museum. Photo by Richard Bowditch
Discover the magic of maritime adventures at South Street Seaport Museum. Photo by Richard Bowditch

Dozens of Fall Day Trip Destinations for Long Island Families

Now is a perfect time for Long Island families to plan a fall day trip or weekend getaway to one of a dozen family-friendly destinations. The weather is cooler, Mother Nature provides some beautiful scenery, and there are even a couple of long holiday weekends that give everyone an extra day to spend together.

To help get you on your way, we’ve put together a list of the top fall getaways for Long Island families this season. Some are close by, while others require a few hours in the car or a ride on a ferry. No matter where you go or how you get there, you’re sure to create some great memories.

For more seasonal travel ideas, check out our Fall Fun Guide.

Fall Family Day Trips Around Long Island

Apples are ripe for the picking on the East End. Photo by Jaime Sumersille

Hop in the car and head east on the Long Island Expressway. Pass through Riverhead and keep on going because Long Island’s North Fork offers much to do for families this time of year. From kid-friendly wineries to fall festivals and pumpkin picking, to biking and hiking paths, there are a host of activities for every member of your family. Crowds can get crazy, so be sure to get an early start. And be sure to visit the quaint communities of Mattituck, Southold and Greenport.

Alternatively, head east on Sunrise Highway to the Hamptons. Stop at one of several communities, where you’re sure to find a street fair, farm stand, or pumpkin patch. Have a bit more time? Keep on going to the end of the Island, where Montauk awaits. Visit Montauk Point Lighthouse and climb to the top to take in the breathtaking view (kids must be 41 inches tall to climb). Walk along the beautiful beaches and check out the many shops and restaurants in town. Get in some hiking or biking at Montauk Point or Camp Hero state parks

Shelter Island is a fun day trip, but getting there requires a short ferry ride from either the North or South Fork. You can take your car over, but once you’re on the island, rent bicycles to explore the 27-square-mile island. Take walks along the beautiful beaches, have lunch in town. Play a round of mini-golf and have some ice cream at Whale’s Tale. Visit Mashomack Preserve, where you can check out the interactive exhibit at the field house before you embark on a hike.

Back to the west, take a short ferry ride from Bay Shore, Patchogue, or Sayville and you can be at one of the many Fire Island communities in no time. Each one offers something unique. Definitely check out Fire Island Lighthouse and the Sunken Forest. Most ferries run through mid-November, but check individual schedules. Insider's secret: Because it lies on the Gulf Stream, Fire Island waters are often swimmable into October.

There is no shortage of walkable, scenic villages all across Long Island, each one perfect for a day of exploring and sightseeing. Check community websites for fall festivals, local events, and sites worth seeking out. Visit the vibrant cities of Long Beach and Glen Cove. Explore the harborside communities of NorthportPort Jefferson, or Cold Spring Harbor on the north shore or head to the south shore and visit Freeport, Long Beach, and Patchogue

Fall Day Trips for Families Interested in Long Island History 

Families can step back in time at Old Bethpage Village Restoration. Photo courtesy of OBVR

History abounds throughout Long Island, so why not treat your family to a daylong outing that is fun and educational? Visit Sagamore Hill, President Theodore Roosevelt’s Oyster Bay home for more than 30 years. Take a guided tour of the Walt Whitman Birthplace State Historic Site, which dates back to 1918. Learn about life during the pre-Civil War era at Old Bethpage Village Restoration, or discover more about Long Island's indigenous people at the Shinnecock Nation Cultural Center and Museum in Southampton.

Spend a day in Stony Brook, where your family can explore the many exhibits at the Smithsonian-affiliated Long Island Museum. Walk among the shops and stop for lunch at Stony Brook Village Center, then tour the grist mill, which is listed on the National Register of Historic Places. Be sure to visit Avalon Park and Preserve for a hike and some duck-watching, and check out the Avalon Sky Lab.

Fall Day Trips to New York City for Long Island Families

The Pershing Square beams sit on the High Line; just be careful where the kids walk. Photo by Rowa Lee/courtesy of Friends of the High Line

For a change of scenery, take the Long Island Rail Road (or drive) to New York City. Pick a neighborhood and start exploring its many sights and sounds. Walk across the Brooklyn Bridge or along the High Line—there's an entrance at West 34th Street, between 10th and 12th avenues. Sample the ethnic diversity of Greenwich Village, check out the city’s many family-friendly museums and parks, including the South Street Seaport Museum. See a Broadway show, enjoy the Columbus Day Parade, and teach your children the art of people-watching. Governors Island, accessed by ferry from Brooklyn or Lower Manhattan and one of our favorite kid-friendly destinations, is open until October 31. 

Fall Day Trips to New England for Long Island Families

Mystic Seaport tells the story of America and the oceans. Photo courtesy of the museum

Hop a ferry from Orient Point and sail over to New London, Connecticut. The crossing takes about 90 minutes. From there, it’s just a 10-mile drive east to Mystic, where there is plenty to keep your family busy for a day or an entire weekend. The main attraction is Mystic Seaport: The Museum of America and the Sea, but don’t forget Mystic Aquarium and, of course, lunch or dinner at Mystic Pizza, made famous in the movie of the same name.

If you have a weekend free, plan a trip to Boston, a city loaded with history and charm. Enjoy the fall foliage as you head up I-95 north. Once you arrive, park your car and walk the Freedom Trail, a 2½-mile route that lets you leisurely meander through the city and takes you to 16 historic sites, including Boston Common, America’s oldest park, Paul Revere House, and Old North Church. If you prefer not to drive, take Amtrak from the New London station to one of four Boston-area stops in less than two hours.

Fall Day Trips to Upstate New York for Long Island Families

Kids will thrill to the Playground of Giants at the Storm King Art Center in the Hudson Valley. Photo by Shira Kronzon

Another destination that is particularly picturesque during the fall is the Hudson Valley. Admire the colorful foliage while hiking and biking along the area’s many trails. There are plenty of farms for apple and pumpkin picking. If you plan on staying the weekend, check out the all-inclusive, family-friendly Rocking Horse Ranch in Highland.

If your family can’t get enough football, why not head to West Point for an Army game? Visitors are welcome to take a scheduled tour of the United States Military Academy and visit the West Point Museum. The pregame pageantry can't be rivaled.

Fall Day Trips to Pennsylvania for Long Island Families

The state of Pennsylvania makes for a perfect fall weekend getaway. Great Wolf Lodge in the Pocono Mountains, with its giant water park and other indoor attractions, is hugely popular with families. For a change of pace, visit the quaint, historic town of Jim Thorpe. Situated in Pennsylvania’s Lehigh Gorge, it offers a walkable downtown filled with shops and restaurants, Lehigh Gorge Scenic Railway train rides, and the annual Fall Foliage Festival. And, of course, Philadelphia is brimming with fall festivals and other events for  families. Visit the Philadelphia Zoo, take in a show at the Free Library of Philadelphia, and stop by one of the city’s many family-friendly museums.

A version of this post was originally published in 2015. 

Montauk Lighthouse
2000 Montauk Hwy
Montauk, NY

Montauk Point State Park
50 S Fairview Ave.
Montauk, NY

Camp Hero
1898 Montauk Hwy.
Montauk, NY

Sagamore Hill
20 Sagamore Hill Rd.
Oyster Bay, NY

Walt Whitman Birthplace Historic Site
246 Old Walt Whitman Rd.
Huntington Station, NY

Old Bethpage Village Restoration
1303 Round Swamp Rd.
Old Bethpage, NY

Shinnecock Nation Cultural Center and Museum
100 Montauk Hwy.
Southampton, NY

Long Island Museum
1200 Route 25A
Stony Brook, NY

Avalon Park and Preserve
200 Harbor Rd.
Stony Brook, NY

Whale's Tale
3 Ram Island Rd.
Shelter Island, NY

Mashomack Preserve
47 S Ferry Rd.
Shelter Island, NY

Mystic Seaport: The Museum of America and the Sea
75 Greenmanville Ave.
Mystic, CT

Mystic Aquarium
55 Coogan Blvd.
Mystic, CT

Mystic Pizza
56 W Main St.
Mystic, CT

Rocking Horse Ranch
600 State Route 44/55
Highland, NY

Great Wolf Lodge
1 Great Wolf Drive
Scotrun, PA 18355

Philadelphia Zoo
3400 W Girard Ave.
Philadelphia, , PA 19104

Free Library of Philadelphia - Parkway Central Library
F 1901 Vine Street
Philadelphia, PA 19003
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