Looking for a charming coastal escape that’s close to the city but feels a world away? I always tell friends to head to Greenport! Tucked on Long Island’s North Fork, this seaside village stole my heart with its maritime charm, local wines, and fresh seafood. Whether you're craving a peaceful waterfront stroll, a little boutique shopping, or a sunset dinner by the harbor, I think you’ll love the way Greenport blends laid-back vibes with just enough adventure.
Best Time to Visit
From my experience, the best time to visit Greenport is late spring through early fall (May to October). That’s when the harbor is buzzing, farmers markets are in full swing, and vineyards open their doors for tastings. I’ve caught ferry rides on sunny afternoons and ended my days with wine by the water—you’ll definitely want to time your trip during these warmer months.
How to Get There
- By car: I usually drive from NYC—it takes about 2.5 hours via the LIE (I-495) and Route 25. You’ll pass through farmland and wineries along the way, so I always leave time for a few scenic stops.
- By train: The LIRR goes all the way to Greenport Station. I’ve taken it when I wanted to skip the drive and just relax—it’s easy and drops you right in town.
- By ferry: I’ve also arrived by ferry from Shelter Island and even New London, Connecticut. It adds a fun, nautical twist to the trip—and it’s perfect if you’re already exploring nearby coastal towns.
Where to Stay
- The Harbor Front Inn – I stayed here once and loved waking up right on the marina. It’s modern and relaxing, with views that make you slow down and breathe.
- American Beech Hotel – If you like staying somewhere stylish and walkable, this spot in Stirling Square is one of my favorites. I sipped cocktails at the bar and walked to everything I needed.
- The Menhaden – Sleek, clean, and right in the heart of town. I borrowed one of their bikes and explored the waterfront in the morning—it’s perfect if you want that modern boutique feel with thoughtful extras.
Best Things to Do in Greenport
Dive Into Nautical History at East End Seaport Maritime Museum -
All Aboard for a Journey Through Time at the Railroad Museum of Long Island -
Step Inside a Historic Landmark at Congregation Tifereth Israel -
Savor Fresh Brews and Local Flavor at Aldo’s Coffee Company -
If You’re Craving Coastal Vines and Ocean Views, Sip at Kontokosta Winery -
Dig Into Creative Eats and Quirky Vibes at Crazy Beans Greenport -
If You Love Seafood and Waterfront Dining, Head to Claudio’s Restaurant -
In Summary...
(and if you want to revisit my photo journey)- • Dive Into Nautical History at East End Seaport Maritime Museum
- • All Aboard for a Journey Through Time at the Railroad Museum of Long Island
- • Step Inside a Historic Landmark at Congregation Tifereth Israel
- • Savor Fresh Brews and Local Flavor at Aldo’s Coffee Company
- • If You’re Craving Coastal Vines and Ocean Views, Sip at Kontokosta Winery
- • Dig Into Creative Eats and Quirky Vibes at Crazy Beans Greenport
- • If You Love Seafood and Waterfront Dining, Head to Claudio’s Restaurant