We originally ran this story in August of 2014–it’s been updated with additional information. After a return trip we’re pleased to report that the North Fork is better than ever.
You don’t need a car to get out of town for a few days. Greenport, on the tip of Long Island’s North Fork is an excellent spot to explore by bike. Between the surrounding vineyards, Shelter Island and the town itself, a fishing village that is re-emerging from some pretty depressed economic times, with tons of new restaurants and shops lining the small downtown, there’s plenty to do, see, explore and taste.
No bike? Rent one. Dan’s Bike Rental includes a basket, lock, helmet, light and map, and they will drop a bike off at your hotel, or meet you at the train or Jitney. Rates start at $25/day, and they will come replace your bike and rescue you if you break down. Do note, these are easy-going, upright stance, city bikes, not serious road bikes. The general area is very flat, but if you’re traveling with speedsters on road bikes you should prepare yourself for a slower ride than the rest of the pack.
How to get there: If you’re planning on renting a bike, take the Long Island Railroad. Considering summer traffic, the three-hour trip is generally faster than the bus, and more comfortable. It is possible to take a bike on the LIRR, but only on certain cars on certain trains–it’s a pretty lengthy list of rules and regulations, and if you’re part of a group with bikes (unless you have nifty folding bikes) forget it. Depending on when you leave, the fare runs from $20-28, each direction. The Jitney on the other hand, is a snap with a bike. Just show up with your bike and they’ll stow it in a luggage compartment and then charge you once you’re on board. The fare is $23 each way ($19 if you reserve online), plus an additional $15 for your bike, and you get complimentary bottled water and chips onboard, usually. There are a few departure points from Brooklyn, as well as many in Manhattan. Check the schedule for departure times and options–it’s very easy to change reservations from your phone, should your plans shift. The downside? Traffic.
Where to stay: Greenport is not the Hamptons, but lodging can still be pricey. The Greenporter, which is located very close to the train, the Jitney and to the center of town is a modernized motor inn with comfy beds, a pool and a restaurant. Prices start around $209 a night for a queen room midweek (they drop slightly, to $179 in the fall), more on weekends and holidays.
About a mile outside of Greenport you’ll find the Silver Sands Motel, which is like entering the land that time forgot, in the best possible way. There’s a pool, and it’s right on the water, with a little sandy beach and a tiny boardwalk where fellow vacationers tend to sun themselves in deck chairs and hold informal and convivial cocktail hours come late afternoon. Rooms range from $150-200 a night in the summer (the cabins have tiny kitchens and come with a daily breakfast of fruit, cereal and muffins). It’s a relaxing spot that feels like a real find. You can sit on the beach, sipping bottles of North Fork rosé and chatting deep into the evening, or commandeer a Weber grill for a cookout. The rooms haven’t been updated in some time, but between the private beach, the pool, which is lovely, and the overall laid back vibe, you won’t mind unless you were planning on spending the weekend watching television and ordering room service. This is not the place for that.
Biking: Figure out how long a ride you want to do and then use this map of local wineries to plot out a course. With tasting, snacking and side excursions, like Horton Point Lighthouse or Catapano Dairy Farm for fresh goat cheese, a 30- to 40-mile ride will likely take most of the day. The terrain is quite flat so you can comfortably cover quite a bit of distance. You can also stick close to to Greenport and focus on nearby tasting rooms. A word of caution: Unless you rented a bike and can call for help, bring some basic repair supplies like replacement tubes and a bike pump. There is very little public transportation and the only bike shop in the area is Country Time Bike in Mattituck. There are a few Uber drivers in Greenport but if you break down in the middle of nowhere with no supplies, you’re going to have a time of it.
There are two main roads along the North Fork, 48 and 25. Spend some time figuring out a route that will take you off those roads as much as possible. While 25 is shady and travels through small towns, 48 is hot, busy and not much fun to bike on. The shoulders are wide, but definitely plan your trip so that you’re off those roads and onto the more scenic and relaxing side roads as much as possible, taking say, Soundview Avenue and Oregon Road which are both just gorgeous.
If you’re not that into wine, or want a shorter ride, head directly to Shelter Island. (More on this below.)
Wine: Here are a few thoughts on vineyards to visit. It’s a gorgeous ride to Shinn Estates along Oregon Road, and they have a menu of small plates to order from. Don’t plan on spreading out your own snacks here, but do plan on sampling a flight of their biodynamic wines. Shinn also has an inn, where room rates start around $260 per night. One Woman Wines is very rustic and lovely, and one of the closer wineries to Greenport. Macari Vineyards is about 15 miles from Greenport, so it makes a good midpoint for your trip, and the tasting room and grounds are stunning, with plenty of spots on the wrap-around porch to relax with a glass of chardonnay. You can purchase cheeses, many of them local, crackers and other wine-appropriate snacks here for a picnic. If you’re feeling like you want to log more miles, head to Paumanok, another five miles past Macari.
Best bites: The restaurant scene in Greenport has exploded over the past few years, and the two spots you most often hear mentioned are Noah’s and The Frisky Oyster. Both serve excellent, fresh seafood, and local ingredients, like duck, heirloom tomatoes, and yes, oysters, stud the menus. Basically, neither the dishes, nor the prices would be out of place in Brooklyn. So do go expecting good food and Long Island-centric wine lists, but don’t expect a bargain.
Sadly, the wonderful and cheap old-school Coronet Diner in Greenport has closed. Across the road from the Silver Sands you’ll find a fairly nondescript restaurant called the Heights Deli Café. They serve all manner of American breakfast staples, but you can also order pupusas, which come served with a red salsa and a bright, vinegary coleslaw. Highly recommended.
For classic breakfast, try Erik’s in Southold. It’s on the way to most vineyards and serves egg sandwiches, pancakes, huevos rancheros and has pretty good coffee. A note on coffee. If you have a cold brew problem, as so many of us do, bring some with you, as you won’t find anything that will satisfy your caffeine cravings on the North Fork. Grady’s and Alchemy Brewlab both make nifty self-contained brew kits where you just add water to a coffee sachet, and then brew it in the bag they provide–ideal for traveling.
Near the water in Greenport, Little Creek Oyster Farm has a tiny spot with picnic tables and outdoor seating serving some of the freshest oysters you’ll find anywhere, plus a Long Island-centric wine list. You can order your bivalves shucked or get a bucket of 24 unshucked oysters for $30 and they’ll set you up with gloves, knives and show you how. The menu is limited to oysters, clams, pickled items and a lackluster clam chowder, so be warned that if you come hungry you may need to figure out a second stop for dinner. And, though they’re the same touristy seafood monstrosities you see in every oceanfront town, there are several lobster-bib-type places on the wharf, including the temptingly-named, Crabby Jerry’s. Keep in mind that dinner service ends earlier here than in Brooklyn, even on summer weekends. Show up at 10pm looking for a table and some places may no longer be seating.
For picnic supplies and snacks, The Market, on the main drag downtown, is a health food store with plenty of snacks and drinks.
Don’t miss: Shelter Island. The ferry to Shelter Island leaves every 10-20 minutes from 6am to midnight, every day. It’s $2 each way for pedestrians, $5 round trip with a bike. The tree-lined roads and water views make for easy, relaxing bike riding, with some hills for a change, and there are a few restaurants and cafes on the island where you can stop in and recharge. Riding to Ram’s Head County Park on the northeast corner of the island is beautiful and relaxing and there’s water access at the end so you can take a dip and cool off.
There are also inns and hotels, and a even a high-end resort owned by André Balazs, the hotel impresario behind The Standard, called Sunset Beach, which, unless you’re a fan of paying $16 for a cocktail while bombarded by droning club music, you should really avoid. If you were playing Sunset Beach Bingo, the squares would include side boob, bad plastic surgery, vanity tattoos, status anxiety, yachts, and midlife crisis. It’s probably worth visiting for just one drink as an ethnographer of New York State. Don’t even think about eating brunch here. Don’t do it to yourself. To be fair, though, their cocktails are delicious.
If you’re feeling ambitious, you could also plan a trip where you take the North Ferry to Shelter Island from Greenport, bike across the island, then take the South Ferry to Sag Harbor to visit Channing Daughters Winery and Wolffer Estate and then spend some time on the beach. It’s possible to take the Jitney back from the South Fork as well, just make sure to reserve a spot, especially on weekends.