Greenport, Long Island – The Perfect Relaxing Destination For Families

A family of 5 on a beach hike in Greenport, Long Island

Greenport, Long Island is absolute heaven. It feels like a small town, it is beautiful, it is on the water, it has great restaurants, cute stores, and even old-fashioned ice cream shoppes. It is the perfect family destination for a day trip or for an overnight stay. As an added bonus – if you live on Long Island – it is only a short drive East without any bridges, tunnels, or tolls!

A family of 5 sitting on a rock at the water in Greenport

Falling In Love With Greenport, Long Island

I fell in love with Greenport three years ago after a friend’s fortieth birthday party out there. I heard how amazing it was for years but never ventured out there myself. For some reason we always traveled west – to Sesame Place, Dutch Wonderland, Cherry Crest Farms, Diggerland any place with a ride and a refillable drink cup. However, this was a different experience entirely.

A family of five standing under umbrella decorations on Main Street in Greenport

This was slower, relaxed, no hustle bustle, just sitting and enjoying life. This was the place we had been looking for our whole lives. Upon completion of our raging party weekend – I immediately booked a family vacation at the same resort for a few weeks later. 

A little girl reaching for a brass ring on an antique carousel in Greenport

My husband and kids shared in my love of this beautiful North Fork town immediately. We quickly fell into our routine of spending mornings and afternoons at the beach with a walk around town to find a cute restaurant for dinner.

Two kids standing at Mitchell Park Marina in Greenport

We added in live music at Mitchell Park or a ride around the antique carousel (complete with brass rings to grab for a free ride) and it was always a great night. Every night was a great night. Every day was a great day.

A family of five on a hike in Greenport, Long Island

Our Favorite Family Restaurants In Greenport, Long Island

A few gems have stuck out over the years. As a quick note – we have approached this trip from a kid friendly perspective. Would I go to all of these places if it was just adults? Some yes – some no. These are amazing, relaxed, fun, casual places. Not getting dressed up on a Saturday night in black pants places. However – I can guarantee that you and your children will be happy that you went to them.  

Three kids in front of the Drossos sign in Greenport

If your kids are like mine and love mini golf, Drossos is a must for your list. The Tick Tock Mini Golf is connected to Drossos Motel and has been a fixture in Greenport for decades. Coupled with this favorite activity is Jenny’s at Drossos the “snack bar extraordinaire” where you can grab some delicious food (including their killer spicy chicken sandwich), fried shrimp, salad, fries, and delicious ice cream. 

A family in Greenport, Long Island

If you are looking to dine in town, our favorite restaurant out there – and quite possibly anywhere – is Crabby Jerry’s. Part of the Claudio’s family – Crabby Jerry’s is located on the pier and is super casual (read: very family friendly). Much like everywhere else in Greenport, you soon learn causal and outside also translates to delicious. We were dying to go back this year, but the rain had other ideas. We did unanimously agree it would be worth an additional day trip out there just to have one of their soft-shell crab sandwiches again. 

A woman at Lavender By The Bay on Long Island

Activities Around Greenport, Long Island

If you’re looking for a nice and relaxing activity in Greenport, we loved Lavender By the Bay in East Marion (right up the road from Greenport). Especially if you are passing through in the summer – this 17-acre lavender field is a must. It is beautiful and filled with unlimited photo ops. I could have brought a book and spent the whole day here enjoying some purple and shade while taking in the scents and scenes. 

A Greenport beach stair case going down

If you are explorers like us you can drive around and check out Greenport’s famous beaches – like 67 Steps Beach – all with long staircases going down to beaches with varying degrees of large boulders. 

Three kids on a hike at InletCounty Park in Greenport

If you like to hike there are tons of options out there including the Inlet Pond County Park. We loved this easy hike that included both beautiful forest and a shoreline stretch. 

Long Island Wineries

Of course, I’d be remiss not to mention the tons and tons of vineyards and wineries out East in Greenport’s backyard. Most are family friendly and offer a great evening activity for all.

A family at Corey Creek Tap Room on Long Island

You can check local listings to find live music, concert series, and food trucks. There is nothing better than sitting with a glass of local wine on a summer night with live music as your kids run through the grapes.

A hand holding Mattitaco tacos on the water in Greenport

Stops Enroute to Greenport, Long Island

Speaking of food trucks – during our most recent trip, we were lucky to visit our favorite food truck – Mattitaco – not once but twice. If you can’t find their Airstream you can always check out their brick and mortar location in Mattituck (just West of Greenport). Mattitaco has become one of our favorite spots to stop as we head East. Their tacos are so delicious and so fresh. Absolute taco perfection… and we don’t joke around when it comes to tacos.

3 kids at Magic Fountain Ice Cream in Mattituck

Our other must-stop spot on the way out East (and let’s be honest on the way home too) is Magic Fountain Ice Cream. Their vast flavor selection is our favorite on Long Island and their unique flavor pairings always get us so excited (feta cheese in ice cream – YES)! We were lucky enough to have quite the sampling this time as we chatted with Magic Fountain’s super sweet (pun intended) owner.

A family of 5 at The Big Duck in Flanders, Long Island

Another cool spot to stop as you head East (especially if you like Long Island landmarks) is The Big Duck in Flanders. Not much more than a quick photo op these days but apparently this duck changed the world of architecture forever. 

A little boy relaxing on the balcony in Greenport

The Most Perfect Relaxing Destination For Families

Greenport is special for so many reasons. It’s a beautiful drive through farms, close to Orient Point (and the ferry to New England), and just a great place to stop and take it easy for a few days. If you want to explore more around the Greenport area, you can also take a ferry ride over to Shelter Island. 

Three kids sitting in a car on the Shelter Island ferry

When people ask what they should do out there, I say “nothing.” Sit, look at the water, read, eat, and relax. For me – there is no better vacation. Even if it doesn’t come with a refillable cup.

Welcome to Greenport sign on Long Island

Published by Stacey Wallenstein

Stacey Gish Wallenstein created The Mint Chip Mama blog in 2013 to share her love and passion for giving children meaningful life experiences and helping moms like her navigate the challenges and benefits of raising children in the New York metropolitan area. Before becoming a full-time mom in 2010, Stacey spent the better part of the preceding decade as a high-end customer relationship management (CRM) professional for some of the most well-known brands in the hotel, luxury, fashion, and beauty industries, such as Harrah’s Entertainment, Chanel and Christian Dior, Inc. She managed customer loyalty programs for thousands of clients around the country and created social media strategies for a span of industries including healthcare services, restaurants, consumer packaged goods, specialty foods, local attractions and retail locations. After 13 wonderful years in Manhattan (the last three of which spent as a city mom), Stacey and her husband moved to Long Island in 2014, where they now reside with their three children (11, 8, and 5). There, she is a founding member of her local Parenting Center, which provides classes and coordinates events designed to educate and inform parents while fostering an environment of support and friendship within the community. Stacey is also an active PTA member ((including a former & current PTA president) as well as a Girl Scout troop leader. Her musings on motherhood, Manhattan, the suburbs, and more can be found here and on Facebook at The Mint Chip Mama. A graduate of the University of Michigan, Stacey has been active in the New York area alumni organization for nearly twenty years, serving as a board member on the school’s University of Michigan Alumni Club of New York City. She also holds a Masters in Psychology from The New School in New York City. For more updates, follow her on Facebook, Instagram, Twitter and Pinterest.

One thought on “Greenport, Long Island – The Perfect Relaxing Destination For Families

Leave a Reply

%d bloggers like this: