Things To Do
Kontokosta Winery
Winery on the Long Island sound
Orient Beach State Park
Admission is $8 per car. Enjoy sweeping views of the ocean and arguably the best beach on the North Fork. Visit the Sun Shine Shack for oysters and snacks or Duryea’s for their lobster salad. Stop by Opties and Dinghies on your way back for yummy ice cream
Croteaux Vineyards
Our favorite vineyard on the North Fork. They serve Rosés only. Get the Chloe!
Lieb Cellars Tasting Room
Modern tasting room with fantastic whites
Goldsmith's Inlet Park
Stunning spot with great walking trails that lead you through the forest to the beach. You need a Southold parking permit to park here, so ask you hotel / airbnb.
Crescent Beach
The best beach on Shelter Island. Public parking available. Grab food at the Roaming Islander food truck
McCall Wines
Spacious and cozy, all-wood tasting room with some of the best wines on the North Fork.
Corey Creek Tap Room
Owned by Bedell Cellars, this is their smaller offshoot where they make small batch wines and wines that are off the beaten path. Killer frosé too.
Matchbook Distilling Co.
Super innovative distillery making creative spirits, aperitivos and wines. They have a create your own gin experience (must book ahead) and offer tours and tastings at their tasting room.
Lenz Winery
A pretty and intimate tasting room with a great white wine flight.
67 Steps Beach
Great insta spot. Rocky beach at the end of a quiet road.
Shelter Island Country Club
Public 9-hole golf course on Shelter Island. Call for tee times.
Greenport Harbor Brewing Company
The original location of the Greenport Harbor BrewCo. They also have a larger location in Peconic. Enjoy a variety of their beers on tap.
Duryea's Orient Point
If you’ve been to Duryea’s in MTK, you know the deal. Come here for their lobster cobb and enjoy the beach club.
The Pridwin
Newly renovated and just opened this August, this spic and span spot has a spa and great waterfront dining.
Fortino's Tavern
The new Fortino’s is a fun dining spot on a dock (indoor dining also available)
Island's End Golf & Country Club
Semi-private 18 hole golf course. The public can book tee times online for a nominal fee. Enjoy beautiful views of the LI Sound while you play a few rounds.
American Beech
Swank boutique hotel with a restaurant, American Beech, and cocktail bar, Black Llama that’s open until Midnight
Brix & Rye
Cocktails and food in town. Open until 1:30am. Speakeasy vibes
Ram's Head Inn
Located on Ram’s Head Island in Shelter Island (which is worth a trip to alone), Ram’s Head Inn is a quintessential Shelter Island institution. There is a restaurant serving lunch and dinner.
Claudio's Waterfront
Raucous spot open until 1:30am with an expansive deck and outdoor bar. This is Crabby Jerry’s sister restaurant and located right next door so we recommend guests stop here after Crabby Jerry’s.
Bike Rentals
Dan’s Bike Rental Bikes for delivery only Call/text 212-380-1119 Nofo Bikes E-bikes for rent only 631-599-9858 310 Front St Greenport, NY 11944 East End Bike Tours Offers guided or self-guided bike tours throughout the North Fork 631-871-1666 13200 Main Rd Mattituck, NY 11952
Oyster Trail
Check out local oyster farms in the area