Towns & Strolls

• Greenport Village – A historic, walkable waterfront town with shops, bars, tasting rooms, and great food.

• Love Lane (Mattituck) – A charming little street with a cheese shop, wine bar, bakery, donut shop, and boutiques. Perfect for a slow morning or grabbing local gifts.

Wineries

• Bedell Cellars – Set in a historic barn, it has beautiful grounds and great rosé.

• Kontokosta Winery – Cliffside views overlooking the Long Island Sound.

• Lenz Winery – Laid-back vibe with excellent Bordeaux-style reds.

• Croteaux Vineyards – Popular rosé-only winery with a cozy outdoor garden.

Breweries

• Greenport Harbor Brewery – Craft beer, casual food, and plenty of outdoor seating.

Beaches & Views

• 67 Steps Beach – Stunning sunsets and Sound views.

• New Suffolk Beach – Calm, relaxing bay beach.

Local Spots

• Wickham’s Fruit Farm – Famous pies, baked goods, and fresh produce.

• Briermere Farms – Legendary fruit pies

Restaurants

Casual & Local Favorites

• Billy’s by the Bay (Greenport) – A true local hangout with good beer, live music, and buckets of seafood.

• Aldo's Coffee Company (Greenport) – Roasted on site, local coffee shop with pastries.

• North Fork Roasting Co. (Southold) – Amazing coffee and breakfast sandwiches in a house setting.

• Legends (New Suffolk) - Sports-friendly local watering hole.

Seafood & Waterfront

• Claudio’s (Greenport) – Iconic dock restaurant with seafood, cocktails, and great boat-watching.

• Minnow (New Suffolk) – Upscale seafood right on the New Suffolk Waterfront.

Great Dinners & Date Night

• The Frisky Oyster (Greenport) – Creative dishes and cocktails.

• Noah’s (Greenport) – Tapas-style coastal dining.

• North Fork Table & Inn (Southold) – Farm-to-table and one of the best dining experiences on the North Fork.