Life in in the city moves fast—but just a couple of hours away, the North Fork of Long Island offers rolling vineyards, relaxing tasting rooms, and fresh coastal air that’s perfect for a midweek reset. If you’re craving a quick break from the hustle and bustle, a weekday wine tasting trip to the North Fork could be your dream escape. Here’s how to plan the ultimate North Fork getaway that’s relaxing, delicious, and low on crowds—but big on charm.
The best part about a Long Island wine trip is how easy it is to reach from NYC—especially midweek, when traffic and train crowds are lighter.
By Car:
Take the LIE (I-495 E) to Route 25. The drive is scenic, especially once you hit Riverhead.
By Train:
Hop on the LIRR from Penn Station to Greenport. Weekday trains run regularly, and you can Uber or rent bikes for vineyard-hopping.
By Ferry (If Coming from Connecticut):
Take the Cross Sound Ferry from New London to Orient Point for a breezy, scenic route straight onto the North Fork.
Weekdays on the North Fork feel like you’ve discovered a local secret. Here’s why it’s the ideal time to go:
No crowds: Forget lines or long wait times at tastings or packed restaurants.
Chill vibes: Vineyard staff have more time to chat and guide you through your tasting.
Better reservations: Score tables at top-rated restaurants without a wait.
Hotel deals: Many boutique inns and B&Bs offer midweek discounts.
If you’re planning a weekday wine tasting trip, these are the must-visit spots:
This boutique vineyard is the perfect midweek destination. Their relaxing patio is ideal for sipping in the sun, and their crisp whites and rosés are beginner-friendly and summer-perfect. Bonus: They often have weekday specials and lighter crowds.
Known for artful blends and a beautiful modern tasting room, Bedell is great for those seeking both sophistication and approachability.
Specializing in sparkling wines, it’s a bubbly midweek treat—great for toasting your spontaneous getaway.
No Long Island Wine Country trip is complete without incredible food. Midweek means shorter waits and quieter tables.
Love Lane Kitchen (Mattituck): A cozy favorite for breakfast or lunch.
Southold General (Southold): Espresso, artisanal sandwiches, and take-out picnic bites.
Touch of Venice (Cutchogue): Classic Italian with local seafood and wine pairings.
Pack a picnic and enjoy it at vineyards like Suhru & Lieb that allow outside food with wine purchases.
A midweek stay means peaceful nights and potential off-peak rates.
The Menhaden (Greenport): Modern luxury with rooftop firepits and free bikes.
The Shoals (Southold): Waterfront charm with oyster tours and sunset views.
Sound View (Greenport): Beachfront rooms, a great on-site restaurant, and laid-back coastal style.
Greenport Village: Boutique shopping, coffee stops, and harbor strolls.
Lavender by the Bay (East Marion): In bloom by mid-July, it’s an Instagram favorite.
Orient Beach State Park: Hike, bike, or lounge by the bay with fewer crowds.
Whether you’re craving crisp rosé, artisanal bites, or just a quiet place to breathe, a weekday wine tasting trip to Long Island’s North Fork is your low-stress, high-reward getaway. With fewer crowds, better service, and just a short trip from NYC, there’s no reason to wait for the weekend.
So, go ahead—sneak away from the city and sip your way into relaxation.
