Blame It on the Rain

Fear and expectations on Shelter Island

May 28, 2009
Outside Magazine

REI Adventures' guided, four-day hut-to-hut trip covers eight miles of the AT daily in New Hampshire's White Mountains before dropping guests off at three Appalachian Mountain Club huts. $460 per person; August–October;


"I'M GOING TO BRING YOU down to the pregnancy level," my wife, Leslie, told me, turning off NPR as we idled in Long Island traffic. I had no idea what she meant, but it didn't sound good. Nor did the forecast: rain, rain, rain. So we'd be spending our last pre-baby adventure holed up inside. Reading. Sigh. Two months later, we'd be Mommy and Daddy. How would we escape then?

At least the trip would be cheap, thanks mostly to the Chequit Inn, which has simple rooms for as little as $90. Plus there was the ferry, the only way to get to Shelter Island and a way to leave behind the sort of people who think, What if something happens at 4 A.M. and I need to go home?

We'd packed our usuals. Me: bike, kayaking gear. Her: books, camera. Saturday began cloudy but dry, with Leslie reading in bed and me pedaling a 25-mile loop. There were real hills (which I didn't expect), holy-crap seaside homes (which I did), osprey nests, and a maze of creeks, ponds, and bays. I got lost and had to crank back to make the free continental breakfast.

At 11 A.M., Leslie dropped me off to meet Jay Damuck, the fifty-something owner of Shelter Island Kayaks, and took her belly and camera to Bootleggers Beach, where she befriended a pair of swans. Damuck unfolded a map of the amoeba-shaped island and pointed out the best of many protected coves. We launched in Coecles Harbor, where Damuck helped establish a water trail. "It stays empty all summer long," he promised as we cruised along the undeveloped shores of the 2,100-acre Mashomack Preserve.

Over lobster that night, Leslie clicked me through her photos of the mirrored water as I tried to will away the impending rain. One more ride would be so nice.

The storm hit at 3 A.M. and we slept in and I woke up ready to do nothing. But instead we drove to a beach to stare into the teeth of the wind and, later, walked into Mashomack, where the frogs cheered the downpour. We had our best meal of the weekend at Mark It with G, a cozy place that specializes in macaroons.

So the expecting was the hard part. You can do a lot in the rain.

EXPENSE REPORT Round-trip ferry ( $22. First-night steamers at the Dory ( $47. Two nights at the Chequit (shelterisland­ $210. Rentals from Shelter Island Kayaks ( $60. Takeout lunch somewhere: $25. Lobster dinner at Two Ed's (631-749-0261): $59. Lunch at Mark It with G (, plus sweets to go: $52.