Explore Long Island’s North Fork with this day trip guide

Jamesport Vineyards offers vineyard views, along with live music and snacks.
Jamesport Vineyards offers vineyard views, along with live music and snacks. Photo Credit: Brooklyn Winery

East End getaways usually entail a car and a pricey overnight stay, even in the off-season. But an affordable day trip can be within reach this fall, as long as you don’t mind enduring hours on the train. Get your fix of wine, fresh seafood and fall scenery with our guide to a Saturday day trip.

8 A.M.

Pack a book or download a movie, grab some breakfast and get on the 8:12 a.m. train from Penn Station to Riverhead ($21.25), arriving at 10:25 a.m.

11 A.M.

Take a 10-minute Uber to your first winery of the day, Paumanok Vineyards (1074 Main Rd., Aquebogue). Try the Cabernet Franc, chenin blanc or a bottle of vintage sparkling for early fall sipping. Be sure to grab a seat on the back deck for gorgeous vineyard views and a dose of sunshine.


For your second stop of the day, walk 5 minutes down the road to Jamesport Vineyards (1216 Main Rd., Jamesport), which boasts a beautiful back lawn where wine sippers get together to enjoy live music and light snacks. Fruit is farmed sustainably, giving way to healthy, terroir-driven wines. The Reserve Petillants are some of the most thirst-quenching bottles on the entire North Fork.

1 P.M.

Lunch at a winery? You bet. Take an 8-minute Uber to Macari Vineyards (150 Bergen Ave., Mattituck), one of the North Fork’s signature wineries. The wines, such as the sparkling Cabernet Franc or chardonnay estate bottles, are deliciously age-worthy — and pair well with the family’s homemade pizza sold from a food truck out back.

3 P.M.

Grab one last Uber for the 20-minute ride to Greenport, the North Fork’s charming town center. Perk up with a coffee at Aldo’s Coffee Company (103-105 Front St.), then take a couple hours to explore the town’s galleries, ceramics shops and specialty boutiques.

6 P.M.

For pre-dinner drinks and oysters, look no further than Little Creek Oyster Farm & Market (37 Front St.), which serves up freshly shucked oysters and local beer all on a harbor-side patio.

7 P.M.

Continue the seaside theme by grabbing dinner next door at Claudio’s (111 Main St.), a historic family-run, waterside seafood joint. Must-haves include the baked clams, crispy calamari and lobster rolls. Pair with a local white wine or a pint of Montauk Wave Chaser IPA.

9 P.M.

It’s time to head back to the city. Take the 9:11 p.m. train from Greenport ($21.25), getting to Penn Station by midnight. And don’t miss it — it’s the last one of the night!