In October, Long Island’s North Fork is a haven for families who flock to the Columbus Day, harvest and Halloween celebrations. Best known for its North Fork Wine Trail, there are still rural, centuries-owned farms and small-town charms along with all the roadside vineyards and family-friendly wineries.
Beyond the abundant activities, and whether your style is casual or classy, you’ll want to sample the NoFo specialty: a lobster roll. The best fresh, lightly dressed, local lobster meat on a brioche or a bun is served from a food truck in the parking lot at North Fork Table and Inn (in Southold); at Braun’s Grill, the eat-in or to-go restaurant at the famed Braun’s Seafood Company, in Cutchogue, where it’s served with coleslaw, potato salad and a pickle; at Love Lane Kitchen, a cheerful gathering spot on Love Lane, Mattituck; and as a BLT at the Jamesport Manor Inn.
Here are 13 activities for fall fun on the North Fork!
Go to a Fair
The annual Riverhead Country Fair, takes place on the Peconic Riverfront Sunday, Oct. 13 and offers pony and amusement rides, food stands and competitions, vendors, plus displays by artists, farmers and homemakers.
Pick apples
In Jamesport, Woodside Orchard offers 27 apple varieties and baked goods, which the multigenerational Gammon family opens for apple picking on weekends, until Columbus Day. Their Aquebogue Orchard is open for picking weekdays (closed Wednesdays) and offers cider tastings and doughnuts in their tasting room.

Woodside Orchards
Pick a Pumpkin
The Harbes Family Farm and Vineyard offers you-pick pumpkins and weekend hayrides. At the Harbes Barnyard Adventure, the eight-acre paid admission area, there are farm animals and multiple choices for fun and games on jumbo jumpers, in the playground, at the sports zone, in the Gnome Hedge Maze or on a trike track.
Pet Goats
Kids can pet and feed the animals at Goodale Farms, Riverhead, which houses chickens, cows, goats, pigs, a pony and sheep. The farm uses no antibiotics, steroids or growth hormones and sells fresh, natural dairy and meat products.
Stare at Stars
On Saturday nights, it’s fun to don a hoodie, bring a blanket and stare at the stars at the Custer Institute and Observatory in Southold. Volunteers greet guests at dusk at the nation’s oldest public observatory (c. 1927). Oct. 5 is a special International Observe the Moon Night event in cooperation with NASA.
Ride a Carousel
Folks flock to Greenport Village to ride one of the 36 horses in the antique carousel housed within the Jess Owen Carousel House, the waterfront glass building in four-acre Mitchell Park. Grab the brass ring to win a free ride (open daily to Nov. 30, except Thanksgiving Day.)
Cruise to a Lighthouse
Take a two-hour (4:30–6:30 p.m.) narrated cruise on Oct. 26, from the East End Seaport Museum, in Greenport, and tour the interior of Bug Light, c. 1871, one of the few offshore lighthouses in the United States that admits visitors. In October, the lighthouse is haunted and ghost stories, costume contests and treats add to the nautical experience. The museum has maritime exhibits, plus a 750-gallon saltwater aquarium.
Visit a Family Friendly Winery
Some Long Island Wine Country wineries welcome children with picnic areas, farm animals, live music, food trucks, non-alcoholic beverages and snacks. In Calverton, there are picnic areas and pony rides at Baiting Hollow Farm Vineyard
. There’s wood-fired pizza at Jamesport Vineyards. There are dozens of petting animals at Martha Clara Vineyards in Riverhead (and it’s a food truck stop!). McCall Wines features an authentic barn and serves burgers, plus picnic space and outdoor games, such as volleyball, bocce and corn hole add fun to a visit to Osprey’s Dominion in Peconic.

Woodside Orchards
Take the Corn Maze Challenge
During apple-picking season, Lewin Farm in Calverton invites families to a five-acre, 20–35-minute corn maze challenge, weekends through October.
View Toy Trains
Toy trains and memorabilia delight Thomas the Train fans in two Railroad Museum of Long Island locations within restored freight houses in Riverhead and Greenport.
Visit a Historic 19th Century Farm
Hallockville Museum and Farm is a non-profit group that illustrates 19th-century farm life for a 250-yea- old family farm. There are guided tours of the interiors and innumerable programs, including how to make handcrafted items and, on Oct. 27, you can meet boat builders at the Maritime Traditions program.
Glean the Fields
Gleaning, the ancient practice of picking non-harvested produce and providing for the needy is always a win-win plan. Garden of Eve — a 50-acre certified organic farm in Riverhead — hosts its annual Gleaning of the Fields event Sunday, Oct. 21 at 10 a.m. to benefit Long Island Cares’s food pantries — which serve more than 250,000 people a year. (Registered participants stay for lunch.) The farm features farm animals, outdoor sofa seating, birthday parties and farm beer.
Celebrate Halloween on Saturday
The Bats Barnacles and Broomsticks Halloween party at Long Island Aquarium will take place 11 a.m. to 4 p.m. Saturday, Oct. 26 with vendors, tricks or treats. Kids who come in costume get a 5 percent discount.
This slice of Long Island stretches from Riverhead east to Orient Point, between the Long Island Sound and Peconic Bay. From Manhattan, cars and jitneys travel 70 odd miles east (via the Long Island Expressway 495 to Exit 73 and follow County Route 58 east); Long Island Rail Road trains connect the city (via Jamaica) to Mattituck or Greenport; and the Cross Sound Ferry links New London, Connecticut, with Orient Point.
Read This Next
5 Family-Friendly Museums in Charleston
Destinations / North America
Aug 22, 2024#WhereverFamily
Insta FeedDestinations / Europe
Oct 23, 2026The Perfect Lancaster County, Pennsylvania, Itinerary for a Preschooler
For my daughter’s 3rd birthday, we decided, rather than more toys collecting dust in every room of our house, to take a weekend trip to celebrate. And, at just about 1.5 hours away from home, Lancaster, Pennsylvania, proved the perfect weekend — and road-trip — destination.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Destinations / Europe
Oct 23, 2026Head to This Spanish Resort for an Immersive Multigen Experience
Vacations including all generations in a family are priceless. When you find a place like Camiral in Giron, Spain, you find a place where you can make family memories to last a lifetime.
Destinations / North America
Oct 22, 2026Why You Should Explore Boston This Winter
Families looking to explore Boston and participate in festive winter happenings will be pleased to know Boston Frostival returns this December for its second season. Frostival’s activations will run for three months and include special holiday celebrations showcasing the city as a winter destination in never-before-seen ways.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Destinations / Europe
Oct 22, 2026Surprising Experiences for Kids in Lanzarote, Spain
The northernmost of Spain’s Canary Islands, Lanzarote sees fewer tourists than the better-known islands of Tenerife and Gran Canaria. But those who choose this smaller island are rewarded with beautiful beaches and experiences they won’t find anywhere else.
ShareThis