THINGS TO DO

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The train and bus both let off at the Greenport Visitor's Dock, located on the picturesque harbor. Vacationers can take in the fresh sea air and browse the village map conveniently placed outside, or pop into the Shelter Island Ferry information booth next door and pick up a map of the town, complete with shop, restaurant and lodging info.

Do not fear, once off the train you will directly face Third Street, and at this point there are only two ways to go—either left or straight ahead. If you continue straight along Third Street, you will shortly intersect Front Street (also Route 25) at the light, one of the town's main shopping rows. And once there, it is virtually impossible to get lost since Greenport's central shopping and outdoor activities are primarily on two easily navigable streets. Make a right and you will see several town maps posted along Front Street to help you get your bearings. When at the corner of Front and Main streets, you've reached the hub of the town.

For adventurous spirits, the Bike Stop on Front Street rents bikes for jaunts around Greenport and anywhere else you'd like to pedal. Tandems are available too, so bring a friend. Rates are $22/day, $18/half-day.

If you like antique shopping, you'll love Greenport. With well over 100 unique stores, boutiques, galleries and specialty shops, this sleepy seaside town is a renowned treasure cove. The two shopping thoroughfares are Front and Main, but be sure to poke around in side streets and places like Sterling Square, Bootlegg Alley and Sterling Commons.

The Furniture Store Antiques, on Front Street, is a must see for its beautiful linens, antique tools and eclectic finds from the turn of the century. Housed in a converted butcher's shop from the 1870s, the cozy store is a relic from the past with its rusty wooden beams and hidden nooks. Ask owner Jim Thompson, and he'll be glad to show you around. Pop in next door at Mixed Bag Antiques (above the whole foods café) and discover gems which could only be found in your grandmother's attic.

Also of interest is Lydia's Antiques and Stained Glass, on Main Street, where you will find a wide array of stained glass lamps and homemade furnishings. Nearby, on East Front Street, is Pair of Paws—not a pet store, but a jewelry and crafts store featuring "funky things from artisans near and far."

A couple of doors down, at the corner of Front and Main streets, stands the colorful red and white façade of Sweet Indulgences, one of the largest confectionery stores in Greenport. The colorful candles and hanging plants will overwhelm the senses, not to mention all the yummy chocolate on display.

Also, don't miss a stroll through Preston's Marine Supplies, located on Main Street Wharf. This revered store is more like a museum, selling everything from lighthouse lamps and antique model ships to furniture. Locals and visitors alike flock here for all their marine hardware and sports equipment.

Art lovers should check out the Artists Gallery, on Main Street, featuring local artists and photographers, and one of the largest Haitian art galleries in the country. Art Sites, on Front Street, is a space for modern art and sculpture.

Conveniently located on Third Street at the Ferry Dock is the old East End Seaport Maritime Museum (closed in the winter). The building is home to informative exhibits and yachting artifacts and memorabilia. Learn more about Greenport's rich maritime history at the Stirling Historical Society and pick up information on the wonderful Victorian homes dotting the waterfront.

If you just want to get away from it all, especially Claudio's Marina, which tends to be a bustling thoroughfare once summer is in full swing, stroll the opposite way down Main Street. Enjoy the relative quiet on one of the town's most scenic routes, which affords lovely views of old Colonial and Victorian dwellings.

In spring and summer, take one of several cruises leaving from Greenport. The Mary E, an historic 75' schooner, sails from Preston's Dock, along the waters of Greenport, Orient and Peconic Bay. The impressive 105' 2-mastered topsail schooner, Malabar, also offers day sails, charters and educational trips. Boats sail from Mitchell Park.

Greenport has more to offer than antiquing and great seaside leisure—there's also great wine! Take a guided tour to some of North Fork's finest wineries. Vintage Tours offers a personalized tour, pick-up and drop-off service, wine tasting and a complimentary gourmet lunch. Reservations are required. But if time doesn't allow, check out Turnhaven Cellar on Front Street, just a block down from the train station, and pick up a bottle of one of the region's superb wines. This quaint, local winery offers complimentary tours and wine tasting from its tasting room. (Closed Jan-March.)

Consider a side trip to explore beautiful Shelter Island. The pristine, naturalistic destination is accessible by ferry, which leaves every 15-20 minutes, and transports cars, bikes and motorcycles. Tickets can be bought at the Ferry Dock, near the bus and train stations on Third Street. Weather permitting, the ferry runs year-round.

Orient Beach State Park, on North Country Road (Route 25), about eight to 10 miles out of Greenport, is only 15 minutes by car, and is open year-round. Not your usual state park, this popular beach haven affords beautiful views of Gardiners Bay and Shelter Island Sound, with several species of birds and wildlife inhabiting the interior. The narrow strip of beach runs four miles, with a handsomely restored lighthouse at the very tip. A taxi from Greenport to the park costs around $15, but at least you avoid the $4 parking fee in the summer when the beach tends to get overcrowded.

LODGING

One of the loveliest B&Bs is right in the heart of the village, the Bartlett House Inn, on Front Street near the beautiful Saint Agnes Church. Open year-round, this 10-room Victorian guesthouse features two fireplaces, cast-iron tubs and stained glass windows. Rates vary depending on season, but range from $115-$180 (higher beginning May 1st, with a two night minimum weekend stay).

The Morning Glory Bed & Breakfast is a short walk up Main Street, a half-mile from the main shopping square. The B&B is conveniently situated near two bays, town beaches and the Horton Lighthouse. Features include three rooms and full breakfast. Room rates range from $125-$175 per night, depending on season.

Watson's By the Bay Bed & Breakfast, on Bay Avenue, sits in the hub of activity, two blocks from Claudio's Marina. Rates range from $100-$150, double occupancy. (Open from Memorial Day to mid-October only.)

Townsend Manor Inn, on Main Street, is a good alternative to the local B&Bs which can quickly fill up during the summer season. This motel inn has 23 rooms and houses both a restaurant and a marina—it's one of the most inclusive accommodations in town, since everything is practically next door. Rooms, suites and private apartments are all available. Rates start at $75/night.

If you'd rather rough it, try the Eastern Long Island Kampgounds on Queens Street and Route 48, about a half-mile west of downtown. Sites are available for tents, trailers and motor homes, and the grounds include a swimming pool, store, laundry and playground. Bikes are also available to rent! Rates range from $27-$33 for the Family Plan, which covers two adults and two children under the age of 17.

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DINING

To borrow an apt expression: "Seafood is King in Greenport." It is fair to say that, although the town also has a variety of other types of restaurants, cafés and pit stops to choose from. But if you're a seafood lover, you've definitely lucked out.

Dine by the docks in style at Claudio's, on Main Street, one of the oldest family-owned restaurants and a landmark since 1845. They offer fine seafood. Around the corner, just along the docks, Claudio's Clam Bar on the Wharf is a popular fish and chips local hangout, with outdoor dining and music in summer. If Claudio's price range is too high for some, Crabby Jerry's, right next door at Main Street Dock, is a great alternate. You'll find affordable entrées with all the outdoor dining ambiance of its swanky neighbor.

The Coronet Luncheonette is an old-fashioned diner serving a hearty selection of breakfast and lunch dishes. Across the street, at the corner of Front and Main, is Bruce's Café and Cheese Emporium, a hip, trendy coffee spot serving delicious soup and sandwiches; sit by the window and people-watch at your leisure.

Stop by the Harbourfront Deli, at 10 Front Street, and feel like you've stepped back in time. Order an old-fashioned egg cream or lemonade, slip into a booth with a good book and hope for another Harrison Ford spotting. For the best hot chocolate and biscotti in town, head to Aldo's Too on Front Street.

Finally, if you have a few minutes to kill waiting for your train or bus back into the city, grab a beer or a bite at the Chowder Pot Pub, on Third Street. It's conveniently located across the street from the station, with bayside seating outside in summer (closed during winter).

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NIGHTLIFE

Enjoy the breezes at Claudio's, where you can enjoy dinner and live entertainment nightly in summer, then step out on the marina for a breezy stroll along the water's edge. Michael's Pub & Restaurant is a favorite late night hang out where locals enjoy the good jukebox and live karaoke on Wednesday nights.

The Village Cinema is located at Front and Third Street in the heart of town, across from Michael's, and is an easy ten-minute walk from most B&Bs. Surprisingly, it's quite large and has some of the best recent movies around, so no need to panic about small town selections.

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TRANSPORTATION

TRAIN:

Long Island Railroad trains run from Penn Station to Greenport. Take the Ronkonkoma branch.

Travel Time: 2 hours, 45 minutes.

Call 718-217-LIRR for details.

BUS:

Sunrise Express Coach Line runs direct from NYC to Greenport, but you need to call and confirm a seat ahead of time, especially during spring and summer. Buses can be caught on 44th Street near Third Avenue.

Schedule: Buses leave and return three times a day.

Travel Time: About 2 1/2 hours.

Call 800-527-7709 for more information.

CAR:

Take the Long Island Expressway east to Exit 73 (County Road 58/Orient). Continue east on Route 58 which becomes Route 25. Greenport is approximately 25 miles east of Exit 73.

Travel Time: About 2 1/2 hours.

CAR RENTAL:

Rent A Wreck is the only choice in town, so you know they're swamped in summer. Be sure to reserve as far in advance as possible during the high season. 631-477-9602. Main Road/Route 25, near the 7-11.

LOCAL TRANSPORTATION

FERRY:

North Ferry Company Inc.

Ferries to Shelter Island leave from the dock near the train station.

Schedule: Numerous times an hour from 6am to midnight.

Call 613-749-0139 for details.

TAXI:

Greenport is small and easy to navigate, which makes the need for taxis virtually none. But should you need one to get out to Orient Beach, or to one of North Fork's many wineries, Maria's Taxi (631-477-0700/765-2221) is the local service. Taxis don't usually wait for passengers by the train station unless it's the busy season.

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TRAVEL TIPS

* The seasons greatly influence this peaceful seaside town, and the best time to see things is early—spring heralds warm breezes and relative seclusion. If you like things hopping, you might want to venture in high summer, or after the crowds ease off, in late fall. Winter tends to be one of the quietest times of the year and most of the town's seaside specialty shops, marinas and B&Bs close for the season.

*Shops tend to close down on Tuesdays and Thursdays, so take into consideration which day of the week you'd like to visit.

* And most importantly—reservations, reservations, reservations! Especially at the small B&Bs around town, which can fill up in no time.

LINKS

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MAP

For a detailed map of Greenport, please click here.