Sign up for our FREE newsletters to get posts like this delivered directly to your inbox.

Long Island's East End: Coastal Charm Meets Autumn Delights

The Hamptons and the North Fork celebrate fall in a big way. The beach town communities and sprawling farms in this Suffolk County area go all out for families to enjoy the season. This popular destination is less crowded after summer, which is a huge bonus when you are looking to check out the sites and drive around the towns.

Traveling for a weekend family trip to the Hamptons from the city will take about an hour and a half to two hours by car, or you can hop on the LIRR for a train ride or catch the Hampton Jitney bus.  

Fall Fun Itinerary for the East End 

Day 1 – Farm Experiences and Beach Walks 

Morning: Memorable fall adventures await at Hank's PumpkinTown in Water Mill, one of the best pumpkin patches on Long Island. This incredible pumpkin farm is set on more than 30 acres and is full of kid-friendly fall activities, 3 unique themed-corn mazes, an apple orchard, a jump pad, massive pumpkin fields, wagon rides, farm fresh treats, tractors, and play structures galore. My kids have been visiting for years and have a blast every season.

We always plan to spend a few hours in the morning at Hank's because there is a ton to do. There is no admission fee to pick a pumpkin or buy some treats in the store; our favorite is the cider donuts. There is an admission fee for the maze park area and activities. We like to go early, because it does get crowded. Parking is free in nearby lots. Dress for the weather, as all the activities are outside.

If you purchase the admission, you receive a bracelet for the day, so you can come and go as needed or to grab lunch. Children under age 2 are free, and there are portable bathrooms and changing stations available at the farm. The photo opportunities are fantastic, so be sure to snap pictures and videos of the kids and family fun. 

My kids always work up a big appetite with all the running, climbing, and interactive play at Hank's after a few hours. A drive into nearby Bridgehampton to walk around and grab lunch is always on the agenda. Candy Kitchen has been serving up diner-style food and ice cream treats in the Hamptons since 1925. This old-fashioned luncheonette is one of the best ice cream spots in the Hamptons and North Fork for kids. You can sit at the counter to eat, or if you have a bigger group, grab a table to blast back to the past. This spot is cash only.

Another alternative spot in town to grab lunch is The Golden Pear, a favorite cafe of locals and visitors. This eatery has everything from bakery goods to sandwiches to hot food options. The Golden Pear also offers breakfast meals if you happen to be swinging through town early and need to find a bite to eat. You order at the counter and grab a table inside or outside to eat and relax. 

Take a picturesque stroll on Cupsogue Beach County Park this autumn. 

Afternoon: A visit to the beach in autumn is one of our favorite family activities when we are out East. The crowds have dispersed, and the weather is usually cool enough to enjoy a nice, long walk to see the ocean and search for some seashells and beach treasures. ​Cupsogue Beach County Park, on the East End, is a favorite among Long Island families, and our family! The park is 296 acres, located at the eastern end of Fire Island and the western end of Westhampton Island, known as Dune Road. This Westhampton spot has a big parking lot and stunning sand, along with a boardwalk. There are no lifeguards off-season, and the snack stand is closed, but taking in the views is still a treat for the whole family. 

After a late afternoon stroll on the beach, you can head into Westhampton Beach Village for dinner and check out some of the cute shops on Main Street. One of our favorite spots to eat in town is Funchos for some fantastic Mexican food. This eatery has a great kids' menu that we love, and you can grab a table inside or out at this fun and casual spot. If the kids still have energy, there is a cool pirate ship playground in town to check out after dinner.    

Day 2 – Apple Picking and Kid-Friendly Wineries  

Morning: Long Island is full of family-friendly apple-picking orchards and apple festivals perfect for the season. One of our favorites is Seven Ponds Orchard in the Hamptons. The orchards are a great size for kids of all ages, with branches low to the ground for the little ones to pick on their own. The variety of apples is always abundant, and depending on the timing, you may be able to pick blueberries, raspberries, vegetables, and sunflowers, as well as pumpkins.

We try to go early to have the orchard pretty quiet while we are picking. There is also a farm playground with an admission fee for the kids, a corn maze, and a fun tractor ride tour of the beautiful farm. The store has fresh fruits and produce, pumpkins, flowers, and more. There are cute photo opportunities for Instagram, and try to grab a little red wagon to pull your apples, because the kids love it! 

Long Island's apple farms are ripe for the picking in the fall. 

An action-packed morning at the apple orchard means the kids and adults will be ready for a delicious brunch or lunch afterwards. The Hampton Bays has family-friendly dining options, and one popular spot, Cowfish, offers a "Little Fish" children's menu with everything from a grilled cheese to grilled salmon. There are dining options for both inside and outside seating. A pirate ship-themed play area will keep the kids happy and busy before and after their meal and give you some time to relax!

Another option is to head to the North Fork for brunch and grab a bite to eat at Main Road Biscuit Co. This family-friendly restaurant offers amazing breakfast and lunch options. Our kids love the chocolate chip pancakes and always ask to go whenever we are in the area. 

Afternoon: The North Fork's popularity has drastically increased over the last few years, in part because of family-friendly vineyards on the East End. Some vineyards have live music and festivals on the weekends with fun picnic areas to hang out with the kids.

Palmer Vineyards in Riverhead has live music and a pizza truck the kids will love on some weekend days. Harbes Family Farm and Vineyard in Mattituck is a kid-friendly stop the whole family will enjoy on the North Fork. There is an admission fee to participate in the huge barnyard adventure and hay rides. There's an on-site wine barn, apple picking, and pumpkin picking. The Harbes Family farm stand has been serving up scrumptious bites and produce for the last 35 years. Be sure to try the sweet corn, apple cider donuts, and seasonal homemade ice cream! 

Family-Friendly Hotels on the East End

1. Hilton Garden Inn – Riverhead

The Hilton Garden Inn is conveniently located across the street from the Tanger Outlets and has an indoor pool, restaurant, and gym for some relaxation time after the water park excitement. Fall rates tend to be a bit lower than the summer average of about $300 per night, with prices higher on the weekends and discounts for frequent Hilton visitors. 

2. Hotel Indigo — Riverhead

This boutique-style hotel is a short distance from the North Fork vineyards and the Hamptons. It is a five-minute drive to attractions such as the Long Island Aquarium. Kid-friendly amenities at this spot include an outdoor pool, and an on-site fitness center for the adults. Hotel Indigo even allows guests to bring one pup overnight. 

3. The Hampton Maid – Hampton Bays

This Hamptons gem is situated on Montauk Highway, just beyond the Hampton Bays downtown and a few minutes from the village of Southampton. The location is ideal for families to explore different areas of the Hamptons and North Fork. Kids and adults alike will delight in the inn’s top-shelf biscuits, muffins, fresh fruit, and, of course, pancakes for breakfast. 

Read Next: Perfect Fall Weekend in the Hudson Valley

All photos by the author