Things to Do in Greenport: 7 Hidden Gems on the Coast

1. Custer Institute and Observatory

Let’s kick things off with a night under the stars. Just a short drive from Greenport, the Custer Institute and Observatory is where you can embrace your inner astronomer. This place has been helping people peek into the universe since 1927. If you’ve never used a massive telescope to look at the moon, planets, or distant galaxies, this is your chance.

Every Saturday night, the observatory opens to the public, so you can get a guided tour of the night sky. The best part? It’s tucked away in the middle of farm country, which means there’s zero light pollution to mess up your view. There’s something pretty magical about looking up at the stars from a quiet field—it makes you feel like you’ve got the whole universe to yourself.

2. Goat on a Boat Puppet Theatre

If you’re traveling with little ones (or just feel like unleashing your inner child), you should check out Goat on a Boat Puppet Theatre in nearby Sag Harbor. They put on hilarious and heartwarming performances that are fun for both kids and adults, plus they offer interactive workshops where you can create your own puppet magic.

Whether you’re catching a show or getting hands-on, it’s a refreshing break from your usual tourist activities. Sometimes you just need to sit back, laugh, and watch some puppets do their thing.

3. Fireboat Firefighter Museum

Next up, for all you history buffs, there’s the Fireboat Firefighter Museum right on Greenport’s waterfront. This isn’t just any old boat—it’s a retired FDNY fireboat that served for over 70 years, even helping out during the 9/11 attacks. 

Now docked in Greenport, the “Fire Fighter” has been turned into a floating museum where you can learn all about its heroic past as you explore the ship. You’ll get to wander through the engine rooms, check out the decks, and hear about the fires it helped fight. It’s like stepping back in time, just make sure to have your sea legs ready!

4. Lavender by the Bay

Ready for a peaceful escape? Head over to Lavender by the Bay in East Marion, where the air is filled with the relaxing scent of—yup, you guessed it—lavender. This family-run farm is a little slice of heaven, especially in the summer when the fields are in full bloom. Walking through rows of purple flowers while the breeze gently rustles through? Yes, please!

Not only is it an Instagram paradise, but it’s also a calming experience that will make you feel like you’ve wandered into the French countryside. Grab some lavender sachets, oils, or soaps from the small shop before you leave so you can take a piece of this blissful spot home with you.

5. Brecknock

If you’re into grand old buildings, then Brecknock Hall is calling your name. This stunning mansion, built in 1857, sits in Greenport’s Peconic Landing community and makes you feel like you’ve stepped into a 19th-century novel. Think sweeping staircases, intricate woodwork, and manicured gardens—an architectural dream.

When there isn’t an event happening (it’s a popular wedding venue), you can book a tour to walk around the grounds and soak in the historic aura. Often overlooked by visitors, this hidden gem is one of our favorites.

6. Southold Bay Oysters

Alright, let’s talk oysters. Greenport is known for its fresh seafood, but if you really want to dive into the experience, book a tour at Southold Bay Oysters. This spot is all about letting you get your hands dirty. 

This short tour shows you how oysters are farmed and teaches you how to shuck your own oysters. Once you’ve mastered the art of shucking, you can sit back and enjoy the fruits of your labor—some of the freshest, briniest oysters around, right on the waterfront. Pair them with a glass of local wine, and you’re living the North Fork dream.

7. Sylvester Manor Educational Farm

Take a quick ferry ride over to Shelter Island, and you’ll find Sylvester Manor Educational Farm, one of the coolest spots for nature lovers. This place is more than 350 years old and started out as a provisioning plantation in the 1600s. Now, it’s a working farm where you can explore walking trails, historic buildings, and gardens.

It’s a peaceful place to take a break from the hustle and bustle, but it’s also packed with stories of the people who’ve worked and lived on this land for centuries. From its Indigenous roots to its modern-day mission of sustainable farming, Sylvester Manor offers a refreshing and reflective look at the area’s deep history.