Visit guide

Weekend on the North Fork

A 2-day North Fork wine country weekend itinerary with hotels, restaurants and a non-wine activity.

2-Day North Fork Wine Country Weekend Itinerary

This itinerary covers a Friday evening arrival through Sunday departure, focusing on Saturday winery visits, Friday and Saturday dinners, Sunday brunch, and a non-wine farm stand activity. It draws from established North Fork spots like Bedell Cellars, Lieb Cellars, McCall Wines, and North Fork Table, emphasizing sustainable, scenic wineries in Cutchogue and nearby areas.

Friday: Arrival and Dinner

Arrive via Long Island Rail Road to Greenport or Mattituck stations, then Uber or rent a car for the 1.5-hour drive from NYC. Check into a winery-adjacent stay like Sannino Vineyard and B&B at 15975 County Road 48 in Cutchogue, offering tastings, sustainable vineyard views, and private rooms.

For dinner, reserve at North Fork Table & Inn in Southold, housed in a late 18th-century home. The menu highlights local ingredients in dishes like farm-to-table seafood and seasonal produce; it's the top-recommended spot for its hospitality history and intimate setting. Book ahead, as it's a North Fork essential.

Saturday: Winery Trail and Dinner

Start at 10 AM with Bedell Cellars in Cutchogue, a family-owned winery using sustainable practices. Enjoy a $25 wine flight on the deck or lawn amid vineyards, often with live music and vendor stalls for a vibrant atmosphere.

Next, 12 PM at Lieb Cellars, overlooking picturesque vineyards. Order a wine flight ($25–$35), wine by the glass, and cheese/charcuterie on the deck—ideal for relaxed tasting without crowds.

Afternoon at 2 PM: McCall Wines in Cutchogue, featuring a casual tasting room, sprawling lawn with picnic tables, and 90-minute reservations. No tour buses allowed; pair flights with grazing boards for a low-key vibe.

End winery hopping by 4 PM to avoid fatigue. For dinner, return to Greenport for casual waterfront options or revisit North Fork Table if available; alternatively, grab picnic provisions from local farm stands for an impromptu vineyard meal.

Sunday: Brunch, Farm Stand, and Departure

Brunch at 10 AM near your stay—try Pip’s Café in Peconic for cozy coffee and light bites, or North Fork Roasting Co. for strong brews and pastries, fueling a relaxed start. Pair with vineyard views if at Sannino.

11 AM non-wine activity: KK’s The Farm in Mattituck, a charming farm stand with seasonal produce, local honey, baked goods, and flowers. Stock up on fresh picks amid North Fork's preserved agricultural landscape—perfect for photos and souvenirs without alcohol focus.

Depart by early afternoon via LIRR from Greenport, wrapping a compact weekend of 3–4 hours driving total.

| Day | Morning/Afternoon | Evening | Key Spots | |----|-------------------|---------|-----------| | Friday | Arrival/Check-in | North Fork Table dinner | Sannino Vineyard B&B | | Saturday | Bedell (10 AM), Lieb (12 PM), McCall (2 PM) | Greenport dinner or picnic | Wineries in Cutchogue | | Sunday | Pip’s/North Fork Roasting brunch (10 AM), KK’s Farm stand (11 AM) | Departure | Mattituck/Peconic |

This plan prioritizes 3 wineries to prevent overload, leverages rail access, and incorporates farm stands as requested. Reservations essential May–October; check for spring events like lavender at Lavender By The Bay nearby. Total word count: 512.