Bedell Cellars [link] - Gorgeous vineyard (a runner up wedding venue for us!)

Sparkling Pointe [link] - For those that like sparkling wines

Kontokosta [link] - Great water views and close to Greenport, can get busy so definitely book ahead

McCall Winery [link] - Probably one of our favorites. You get to sit in refurbished horse stalls as seating areas

Rose Hill Vineyards [link] - Formerly Shinn Estate, small and humble spot with good wine options

RGNY [link] - Great all around spot , indoor and outdoor seating options

Greenport Harbor Brewing Company [link] - Right in downtown Greenport, cute tasting room

Jamesport Farm Brewery [link] - Located next to their farm, take advantage of their food trucks!

Matchbook Distillery [link] - Create your own gin at this Greenport distillery

Claudios / Claudios on the Waterfront [link] - Very cool wrap around bar and good seafood, on a pier into the bay

American Beech Restaurant [link] - Cool decor and ambiance, indoor/outdoor

Ellens on Front [link] - Delicious food, quaint family owned spot

Green Hill BBQ [link] - If you are looking for a meat heavy option, this is a good one

Anker [link] - Great seafood and upstairs bar

Kontiki [link]- Tropical, asian fusion with fun tiki vibes and tapas style food

Brix and Rye [link]- For the cocktail lover, great pizza options for a more informal dinner

Grana Trattoria [link] - Great Italian spot in Jamesport

Jedidiah Hawkins House [link] Very cool , old Victorian house for dinner, also in Jamesport

A Lure [link] Great seafood spot on the water

Waypoint [link] Waterfront restaurant with a menu full of fresh caught seafood options and locally grown produce

The Preston House [link] Modern American cuisine with unique cocktail options

North Fork Doughnut Company [link] Not to be missed! Baked fresh each day and offering the most eclectic flavor options.

Magic Fountain [link] A legendary spot for some amazing ice cream!

The Treatery - [link] cookies, cupcakes, chocolate, and more!

Blue Duck Bakery - [link] Delicious cakes, breads, and pastries

Roadside Farms

There are a bunch of roadside farms where you can pick pumpkins, get get fresh apple cider and pick up other fresh veggies to bring home. One of our favorites is Harbes Family Farm in Mattituck. (Fun fact: we lived right next to it for a month during Covid!)

Another one for locally grown items to explore is 8 Hands Farm - be sure to visit their farm store and café. A great stop for a true farm-to-fork experience.

Hiking Trails

There are a bunch of trails and beaches to take a walk if the weather is nice. Hallock State Park Preserve was one we explored during our summer month out here. You can also check out Orient Beach State Park for a scenic walking route and a beautiful beach.

Ferry to Shelter Island

Take a quick ferry ride (maybe 5 min) over to Shelter Island to walk around or go explore their beaches. There is also a quaint public golf course that John and I have played. [Ferry schedule here]

Walking down Love Lane in Mattituck

There are a bunch of cute shops including a delicious cheese shop and, of course, Love Lane Kitchen.