Base: Greenport, both nights. Take the Hampton Jitney North Fork line from Manhattan at 9:00 a.m. (fall schedule, daily); it reaches Greenport at 11:35 a.m. The rest of the day is on foot within a few flat blocks: Front Street, Main Street, Mitchell Park on the harbor and the North Ferry slip. The ferry’s walk-on fare is $3 each way. Pace: easy for a group: about two hours on the bus, flat village blocks, then a long lunch and a rest at the hotel before dinner.
Coffee and the bus out
Where to eat: pick up pastries and coffee at Bourke Street Bakery inside Grand Central Terminal, open daily from 6 a.m., then walk to the Hampton Jitney’s East 41st Street stop between Third and Lexington Avenues. Buy tickets ahead on the Jitney site and sit together; the ride is about 2½ hours.
The bus leaves the city through Queens and runs out along the middle of Long Island before the fields and vineyards begin past Riverhead. Watch for the first farmstands and vine rows near Aquebogue: that is the start of the North Fork.
Expert tip: check the fall schedule the week you go. The North Fork line’s schedule effective October 15, 2026 runs one morning bus out at 9:00 a.m., so it is worth booking all your seats together.
Lunch on Front Street
Where to eat: walk from the Greenport stop to Front Street Station, a casual restaurant and bar on Front Street that opens for lunch from noon, Monday to Saturday. Order a round of chowder and fish sandwiches and settle in.
Afterward, browse Front Street and Main Street: old brick and clapboard shopfronts, bookshops, galleries and boutiques. Greenport has been a whaling port, a fishing port and an oyster town, and the working boats are still in the harbor a block away.
Mitchell Park and the harbor
Walk down to Mitchell Park and Marina on the harbor, a free waterfront park with a boardwalk, benches and views across to Shelter Island.
Sit on the boardwalk with coffee from Blue Duck Bakery Café on Front Street, open daily from 8 a.m. to 4 p.m., and watch the fishing boats come in. This is the classic Greenport view and the best place to get your bearings.
A walk-on ride on the North Ferry
Walk to the North Ferry slip in the village and ride the small car ferry to Shelter Island as walk-on passengers. The fare is $3 each way, the crossing takes about 10 minutes, and boats run every 8–15 minutes by day. Stand on the open deck for the harbor view back to Greenport.
Ride over and straight back, or step off for a short walk along the road above the landing before the next boat. Be back in Greenport by late afternoon to change before dinner; the late boats run until about 11:45 p.m. on weekdays.
Where to eat and stop
- Breakfast · Bourke Street Bakery (Grand Central) — pastries and coffee inside Grand Central Terminal before the bus; open daily 6 a.m.–9 p.m.
- Lunch · Front Street Station — a casual restaurant and bar on Front Street; lunch from noon, Monday to Saturday.
- Dinner · Ellen’s on Front — a Greenport restaurant at 38 Front Street; Friday dinner 5–9 p.m. Reserve for a group.
- Quick stop (snack): Blue Duck Bakery Café — coffee and pastries on Front Street; daily 8 a.m.–4 p.m. per its listing.
- Quick stop (other): The North Ferry — a $3 walk-on ride each way to Shelter Island; about 10 minutes across.
Grand Central → the Jitney stop on East 41st Street: about 5 minutes on foot. Manhattan → Greenport by Hampton Jitney: about 2½ hours. Greenport stop → Front Street: about 5 minutes on foot. Front Street → Mitchell Park: about 2 minutes. Mitchell Park → North Ferry slip: about 5 minutes on foot; the crossing is about 10 minutes each way.
Where to stay
- The Menhaden (Greenport) — a renovated hotel in Greenport village, a short walk from Front Street and the harbor.
- The Harbor Front Inn (Greenport) — or an inn on Front Street across from the harbor, open all year.
Dinner: at Ellen’s on Front, 38 Front Street; reserve for a group.
Tomorrow: wine country by taxi, starting about 20 minutes west at Horton Point.
Bad-weather plan
Rain on Day 1? Front Street’s shops, galleries and cafés are made for a wet afternoon. Skip the ferry in a storm or high wind, and sit out a downpour over a long lunch and coffee at Blue Duck instead.
Stay: Greenport base · Anchor: the North Ferry · book the Jitney seats together
Good to know: Greenport is small and walkable; the Jitney stop, Front Street, Mitchell Park and the ferry slip are all within about a ten-minute walk of each other.
