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!
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.
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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