Falling for Fall Kids Activities on Long Island


With the end of the summer season, comes the busy fall season. Kids are back in school, routines are normalizing and the real estate market is picking back up. Fall is a great time to do things with kids throughout Long Island. We asked agents, who also are parents, what some of their favorite fall activities are with children on the East End. What do they recommend to clients with families and how do some of these attractions impact real estate sales?

Ryan Springer

One of the great aspects of living on the North Fork is being able to enjoy my favorite season, which is fall. My children and I love to take advantage of a slightly less busy time and soak in the last few days of the beach and surfi ng in the Hamptons. The ocean is still warm and the crowd is light. We have a strong love of the water and also enjoy many days boating and fi shing, and are often times the only boat out. With the advent of so-called “agritainment,” there is also something for all ages to enjoy at many local farms. It’s been my experience that many day trippers have fallen in love with our region and return to purchase a home of their own to enjoy the wide open space or be on or closer to the water. I can’t say I blame them, what’s not to love? Whether it be wine tasting for the adults, pumpkin and apple picking or hay rides for the kids, or boating for the family, the North Fork truly has tons to offer. Just don’t tell too many people, us locals try to keep it a secret!

Julia Krispeal

As the summer sun dips below the horizon, Long Island awakens to the bustling charm of fall. With children returning to school and routines finding their groove, It’s an ideal time for family adventures and a fresh look at the real estate market across the East End. It’s a season of change, and what better time to explore the beauty of Long Island with your family? Many local real estate agents such as myself, who are parents, eagerly share their cherished autumn activities. I always recommend pumpkin-picking escapades at orchards like Hank’s Pumpkintown or Harbes Family Farm. There are fall festivals almost every weekend through Thanksgiving. Harborfest, Autumn Fest and even Long Island’s well-known Oyster Festival are all popular choices for families of all ages! The Southampton Octoberfest and Montauk Seafood Festival draw crowds of locals and visitors alike. These events create a sense of community and often influence potential buyers, showcasing the region’s vibrant culture and fostering emotional connections to neighborhoods. Community-focused events such as harvest festivals foster a sense of belonging and strengthen the emotional ties between families and their prospective neighborhoods. This connection often plays a pivotal role in real estate decisions, transforming fall into a season of both change and opportunity in the housing market.

Pauline Spiller

When the kids go back to school it is technically still the summer season, however, it immediately transitions into fall with the cool crisp air at the morning school bus pickup. Although my youngest child is hitting the age of being an adult and doesn’t take the bus anymore and my middle child is away at college, I will get to do it all over again with the newest addition to our family, my granddaughter. Every year our annual tradition of apple picking out east is what we look most forward to doing during this time of year. Breeze Hill Farm’s apple orchard, in Peconic is one of our favorite places to go. BHF also has a special place in my heart as it is where my oldest daughter got married. As a realtor, I love being that entrusted person with the source of information and resources for my clients, especially those with families on what to do on Long Island. Not only during the fall season but all year round. When I am exploring the island with my own family, I always keep in mind what buyers may be looking for when purchasing their home, as far as location and amenities in the areas so I can help match-make them with their perfect home. Local business is what keeps the real estate market thriving so it’s important to support.

Michael Furino

We love going to all the local farms and nurseries in the fall. Usually Hicks, Heritage Farm and White Post Farms have great activities for the kids and are great venues to get out of the house for a few hours. I think these attractions can slow sales slightly because people are busy this time of year and may not be house shopping as aggressively. We also usually see a slowdown in sales because buyers who needed to be in for the school year have already purchased and there’s just less on the market but with the inventory so low, homes are still seeing quick sales when priced correctly. It’s always tough to pinpoint exactly why sales are up or down but the market still seems to be healthy for the time being.

Molly Deegan 

Following the bustle of the summer season on the East End, the calmer energy and cooler temperatures open the door to a wealth of activities for families. With no shortage of things to do, it is no wonder why the East End remains such a desirable place to buy a home. Harvest season is the perfect time to visit the many working farms and orchards that anchor the East End to its more rural roots. Those following the crowd will find plenty of entertainment at destination spots like Hank’s Pumpkin Town in Water Mill, or the ever-popular Harbes Family Farm on the North Fork in Mattituck. For a quieter dip in the seasonal activities, Wickham’s Fruit Farm in Cutchogue, Waterdrinker Family Farm in Manorville, or one of my personal favorite farmstands, Briermere Farms in Riverhead, never disappoint. (Be sure to try their chocolate cream pie!) Stop for a tasting at one of the many wineries or grab a pint at one of the East End’s popular breweries like the Jamesport Brewery or the Riverhead Ciderhouse, where there is often live music on the weekends. As a busy parent, business owner, and homeowner on both the North Shore and the North Fork, I can attest to the fact that the proximity to so many wonderful places, the beautiful scenery, and the abundance of seasonal activities across the Island all help maintain a healthy local real estate market.

Bridgit Elkin and Eric Elkin

A big part of what makes Fall on the East End so wonderful is that we’re able to take advantage of what summer offers, without the crowds and with the benefit of more reliable structure in our schedules. Warm, sunny days might mean a trip to the beach, Orient State Park, Greenport’s carousel or the adventure of choice for our two girls (ages 2 and 4), a trip to the Montauk lighthouse and museum with a stop at Greenport’s Goldsmith’s toy shop on the way home. Perfect rainy days could bring a trip to the Long Island Aquarium in Riverhead or the Children’s Museum of the East End in Bridgehampton (we have an annual membership and go often). Most seasonal businesses remain open through the fall and our family takes full advantage, as do our clients. Of course, there is apple picking, corn mazes and plenty of entertainment to be had at the many beautiful farms we have out here on the East End. Experience the “off-season” on the East End and you quickly learn there is a wonderful year-round lifestyle to be had out here this equates to added value for anyone considering the region as a second or primary homeowner.