Your Perfect North Fork Weekend Itinerary: Summer Edition

As the sun-drenched days grow longer and the ocean breeze warms the air, the North Fork of Long Island bursts into full summer bloom. Imagine vineyard picnics, clambakes by the bay, and small-town charm set to the soundtrack of cicadas and waves. Whether you're craving relaxed leisure or coastal adventure, the North Fork offers a perfect escape — and at its heart is The Shoals, your waterfront home base between Southold and Greenport.

Here’s how to spend the ultimate summer weekend on the North Fork:

Friday Afternoon: Check-In & Chill Your weekend starts at The Shoals, where breezy suites and marina views create the perfect vibe. Whether you arrive by boat or car, embrace a slower pace of life. Unpack, pour a refreshing local rosé, and relax on your private balcony as the harbor softly hums in the background.

Friday Evening: Sunset, Seafood & Small-Town Strolls Start with a Sip: Enjoy a glass of chilled rosé with sweeping Sound views at Kontokosta Winery, just minutes away.

Dinner Reservation: The Frisky Oyster in Greenport is a must. The Oysters Friskafella are legendary, and the vibe is upscale yet relaxed.

Post-Dinner Wandering: Enjoy the golden hour in Greenport Village. Ride the historic carousel, get an ice cream cone, and explore charming waterfront shops.

Saturday Morning: Wake, Walk & Wander Caffeine & Coastline: Fuel up at Aldo’s Coffee Company with their signature biscotti and strong brew, then head to 67 Steps Beach for a peaceful stroll along the rocky shoreline.

Weekend Bonus: If it's Saturday, visit the Greenport Farmers Market, where local vendors sell everything from fresh produce to North Fork-made jams and pickles.

Saturday Afternoon: Vineyard Vibes Summer is for sipping. These wineries are all within an easy drive from The Shoals.

• Bedell Cellars – Lush grounds and award-winning blends

• Pindar Vineyards – Music, food trucks, and sunflower fields

• Sparkling Pointe – Bubbly tastings in an elegant, French-inspired room

Take your time. No need to rush when each glass is a celebration of summer.

Saturday Evening: Waterfront Dining & Nightcaps Casual by the Bay: Claudio’s Waterfront is a North Fork icon. Fresh seafood, great cocktails, and a lively dockside scene.

Refined and romantic: North Fork Table & Inn elevates local ingredients into a tasting menu worth lingering over.

Back at The Shoals, enjoy the quiet of the marina, a starlit sky, and maybe a nightcap on the deck.

Sunday Morning: Brunch & Boutique Finds Brunch Spot:Bruce & Son serves brunch done right — think duck hash, sourdough pancakes, and farm-fresh everything.

Boutique Browsing: Before you head home, explore local gems like:

• Lido – Coastal-chic fashion

• The Weathered Barn – Artisan décor and gifts

• One Love Beach – Surf gear and summer-ready essentials

Sunday Afternoon: Choose Your Adventure For the Creative Soul: VSOP Projects gallery offers a rotating display of thought-provoking art.

For Nature Lovers: Take a walk along Arshamomaque Preserve’s peaceful trails and enjoy the sights and sounds of summer.

For One Last Toast: Stop at Macari Vineyards in Mattituck to end your weekend with sustainable wines and sweeping vineyard views.

Before You Leave: One Last Bite Squeeze in one more bite if time allows:

• Southold General – Grab a gourmet sandwich and coffee for the road

• Noah’s – Creative small plates in a laid-back, nautical setting

Why The Shoals Is the Ultimate Summer Stay

• Waterfront suites with marina access

• Prime location between Greenport and Southold

• Complimentary cruiser bikes

• On-site food truck and summer programming

• Personalized tips from local-savvy hosts

At The Shoals, summer isn’t just a season — it’s a state of mind.

🌞 Ready to Make It a North Fork Summer to Remember? Book your stay at The Shoals and let your North Fork weekend begin.