Tour de Shelter Island

A scenic bike tour around the Island in between the Forks


July 22, 2007

They come for the quaint shops, low-key beaches and gorgeous views of Gardiners Bay. Each summer, thousands of tourists flock to Shelter Island, situated between Long Island's twin forks, many arriving by ferry with their cars.

But for day trippers who want to experience the island's natural beauty without waiting at one of the ferry terminals in a long line of traffic, there is another way. Bike it.

"It's just a nice way to spend the day, whether you do all of it or part of it," said George Waldbusser, who has organized an annual ride around the island since 1981 and leads the informal group Bike Around Long Island.

The island's roads are fairly flat, winding past the sprawling vacation homes of the wealthy, pockets of oak and beech woodland and swaths of pebble-strewn beaches.

Although there are no prolonged climbs, a handful of steep sections of terrain make for a moderately difficult ride. The hills can be eliminated from the route by taking a variety of short cuts.

Waldbusser recommended going on some training rides before hitting up Shelter Island.

"You don't want it to be the first ride of the season," he said. "You want to go out and enjoy the day. You don't want it to be painful."

Shelter Island is accessible by ferry from two points: Sag Harbor and Greenport. From Greenport, the ferry trip, which costs $5 roundtrip including bike, is brief, only about 10 minutes. There are two lots at the terminal where parking is free. The ferries run every 15 minutes between 7:30 a.m. and 10:30 p.m. If you miss the ferry, kill a few minutes at the East End Seaport Maritime Museum.

The ferry landing on the south end has no amenities and no public restroom. It is about three miles from town. At the north end, bathrooms are at the ferry landing and a Mobil station in Deering Harbor.

I chose to start my adventure from Greenport because the ferry lands at the north end near the island's commercial hub. If you don't have a bike but want to rent one, Piccozzi's Bike Shop, behind the Mobil station, is about a five-minute walk from the terminal. (Bear left where Route 114 forks.) The shop rents bikes for the hour ($10-15), half day ($15-20) and full day ($20-25). Prices vary depending on the kind of bike, and helmets are available.

The shop is the only place to get air for tires or help fixing mechanical problems, such as loose brakes or skipping derailleurs.

If you forgot water or lunch, stock up at the Island Food Centre, which has bike racks, across the street from the gas station . There are several eateries along St. Marys Road and South Ferry Road, but with all the sightseeing to do, it might be a while before you reach them. The market is also a hangout for cyclists and a good place to ask for route suggestions.

Another favorite watering hole for cyclists is Planet Bliss, which serves organic cuisine, on Route 114 at Duvall Avenue. It is a more convenient lunch stop if coming from the south ferry terminal.

I ran into some difficulty navigating Shelter Island's intricate network of streets as a result of two of my personality traits: I hate relying on maps and will only ask for directions as an absolute last resort. After my first mistake -- missing a major turnoff to reach big Ram Island -- I was checking my map often, which required frequent stops.

Print out your route before leaving home and tape it to your handlebars. The island not only has many streets, but they commonly have more than one name.

Ambitious riders can combine the two. Eliminate the Rams Island section to avoid two of the larger hills on the route. Families with young cyclists can opt for an out-and-back trip to play miniature golf course, kayak in Coecles Harbor or seashell hunting on any one of the island's several public beaches.

Two suggested routes:

Big Loop

From the north ferry slip, bear left on Route 114. Coast downhill into Deering Harbor. Stop to fuel up on sandwiches at the Island Market or one of the nearby restaurants.If you're not squeamish about leaving your bike unattended, eat lunch on the dock behind the Island Market and watch the boats pull in and out of the harbor.

Continue on Route 114. Turn left on Winthrop Road, which parallels the coastline and will take you through a mix of salt marsh and harbor views. Turn left on Dinah Rock Road, which becomes Gardiners Bay Drive. Here the landscape takes on a more rural feels as you pass widely spaced houses.

Turn left on Ram Island Drive. Waves lap onto sandy beach on both sides of this narrow spit of land. Don't forget to look up at the giant stick nests built by ospreys on top of the telephone poles. At the summit of the first climb is the historic Ram's Head Inn . You can stay straight or bear right because the road here is a giant loop. Make sure to stop at Reel Point Preserve at thepeninsula's tip. This is one of the few sandy beaches on the island, and it has gentle waves.

Retrace the route to the island's mainland. Turn left on Gardiners Bay Drive/Ram Island Road. About a mile up the road, the Whale's Tale will be on your right. Bear left on St. Marys Road. Havens House, a museum, is on your right about a half mile. Mashomack Preserve is a few hundred feet on your left. Bikes are not allowed on the trails. Bike racks are available at the visitor's center.

Another quarter of a mile, turn right on Midway Road, which snakes past past narrow inlets with moored sailboats. Follow the road north and stop at Tuck Shop for ice cream. Turn left on West Neck Road, then right on Sunnyside Drive. Meander back to the ferry landing via the Heights.

Small Loop

Ride past the lacy Victorian houses in the Heights on Grand Avenue. Turn right on Prospect Avenue. Turn right on Serpentine Drive. Left on Shore Road. Right on West Neck Road. Left on Brander Parkway.

To get to Shell Beach, turn left on Oak Tree Lane and follow to the end. To complete the loop follow Brander until it turns into Peconic Avenue. Turn Right on Lilliput Lane and left on Brander. Bootleggers Alley will be on your left. Turn right on Rocky Point Avenue. Left on Shore Road.

One of the steepest hills on the island is just after Crescent Beach. At the top of the hill, turn left on Sunnyside Drive and head back through the Heights.

Top 10 stops along the way

1) Deering Harbor - Stop for some lunch at Island Food Centre and watch the ships pull into the harbor.

2) Reel Point Preserve - Strip off your socks for a stroll along the preserve's sandy spit.

3) Whale's Tale or Tuck Shop - Both serve icecream. The Whale's Tale has an 18-hole miniature golf course with a maritime theme. It has statues of a gray whale,leaping dolphins, seahorse and a seal balancing a red ball on its nose. It's the perfect halfway stop if you're doing the big loop. If the kids are tired, it's easy to head back to town by a shorter route along Manwaring and North Ferry roads.

4) Havens House - This historic house and museum, run by the Shelter Island Historical Society, was built in 1743 by one of the first families to settle on the island. It is open Fridays through Sundays, 10 a.m. to 2 p.m.

5) Mashomack Preserve - Bicycling is not allowed in the park, but there is a bike rack at the visitors center. The park consists of 2,100 acres and 10 miles of coastline. Trails range in length from 1.5 miles to 11 miles. The preserve is open daily from 9 a.m. to 5 p.m.

6) Shell Beach - Just one of the island's many hidden beaches, Shell Beach is only accessible by bike or foot. Follow Oak Tree Lane until you hit the sea.

7) Bootleggers Alley - Shelter Island has a long history of smuggling, dating back to the 1600s when it was bought by Barbados sugar merchants who harvested the island's oak trees for barrels to ship rum. The alley became indispensable, once more, during the Prohibition era.

8) The Heights - Browse the quaint antique shops, galleries and boutiques around Bridge Street. When cycling, be careful of impatient drivers, particularly during the weekend's high traffic days. The streets are narrow and there isn't a lot of room for bikes. There is a pharmacy if you need to tend scrapes,bruises or mosquito bites or if you need sunscreen.

9) Coecles Harbor - Get away from the hubbub at the northern end of the island by going kayaking in this peaceful harbor.

10) Crescent Beach - Stop on the western edge of the island for a cocktail or two at Sunset Beach restaurant, but don't have too many because a steep climb up Shore Road awaits you.

What to bring

1) Plenty of water and a snack

2) A windbreaker or nylon shell in case the wind picks up or you get caught in an unexpected thunderstorm.

3) Bathing suit and towel if you planning on swimming at any one of the island's

4) Bicycle pump and spare tube and tire irons for changing a flat

5) Sunscreen

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